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Chemistry of Heterocyclic Compounds

 
Articles from the last few issues of Chemistry of Heterocyclic Compounds
 

Synthesis of 6-alkyl-2-dialkylaminomethyl-7-hydroxy-3-(4-methylthiazol-2-yl)-4H-chromen-4-ones

  [CiTO]
In Chemistry of Heterocyclic Compounds, Vol. 48, No. 8. (2012), pp. 1181-1186, doi:10.1007/s10593-012-1119-7

Abstract

Amination of 6-alkyl-2-chloromethyl-7-hydroxy-3-(4-methylthiazol-2-yl)-4H-chromen-4-ones by secon-dary cyclic amines gives the corresponding 2-dialkylaminomethyl derivatives. ...

 

Synthesis of 1-aminonaphtho[1,2,3-cd]indol-6(2H)-ones

  [CiTO]
In Chemistry of Heterocyclic Compounds, Vol. 48, No. 8. (2012), pp. 1177-1180, doi:10.1007/s10593-012-1118-8

Abstract

A novel method has been developed for preparing N-substituted 1-aminonaphtho[1,2,3-cd]indol-6(2H)-ones by nucleophilic substitution of the nitro group in 1-nitronaphtho[1,2,3-cd]indol-6(2H)-ones. ...

 

4-hydroxy-2-quinolones. 203*. Reaction of 1-hexyl-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acid 4-pyridylmethylidene hydrazide with bromine

  [CiTO]
In Chemistry of Heterocyclic Compounds, Vol. 48, No. 8. (2012), pp. 1200-1203, doi:10.1007/s10593-012-1122-z

Abstract

It has been shown experimentally that upon the reaction of 1-hexyl-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acid 4-pyridylmethylidene hydrazide with molecular bromine in glacial acetic acid not only the azomethine carbon atom is brominated, but also the position 6 of the quinolone ring. ...

 

Direct C–C Coupling of Cyclic Aldonitrones with 1,2,4-Triazines Using S N H Reactions

  [CiTO]
In Chemistry of Heterocyclic Compounds, Vol. 48, No. 8. (2012), pp. 1213-1219, doi:10.1007/s10593-012-1124-x

Abstract

New nitrogen heterocyclic derivatives were obtained by a direct uncatalyzed by metals C–C cross-coupling of a cyclic aldonitrone lithium derivative with 1,2,4-triazines. ...

 

Preparation of N-phenylbenzo[h]quinolinium derivatives labeled with tritium

  [CiTO]
In Chemistry of Heterocyclic Compounds, Vol. 48, No. 8. (2012), pp. 1196-1199, doi:10.1007/s10593-012-1121-0

Abstract

The possibility of a direct phenylation of benzoquinoline nitrogen atom with nucleogenic phenyl cations has been demonstrated. A simple method has been developed for obtaining previously unknown tritium labeled N-phenyl derivatives of benzo[h]quinolinium, which are promising radioactive markers for studying the biological action mechanisms of medicinal substances containing the benzoquinolinium structure. ...

 

Substituted ureas based on 2,6-dimethyl-3,5-pyridinedicarboxylic acid azides

  [CiTO]
In Chemistry of Heterocyclic Compounds, Vol. 48, No. 8. (2012), pp. 1187-1195, doi:10.1007/s10593-012-1120-1

Abstract

Under Curtius rearrangement conditions, 2,6-dimethyl-3,5-pyridinedicarboxylic acid azides form the corresponding isocyanates which react in situ with ammonia, primary and secondary amines to form mono-, di-, and trisubstituted ureas. The reaction of the 5-ethoxycarbonyl-2,6-dimethylnicotinic acid azide with imidazole under these conditions gave symmetrical N,N'-bis[5-(ethoxycarbonyl)-2,6-di-methylpyridin-3-yl]ureas. ...

 

1-Cyanoacetyl-3,5-dimethylpyrazole – effective cyanoacetylating agent and a new building block for the synthesis of heterocyclic compounds (Review)

  [CiTO]
In Chemistry of Heterocyclic Compounds, Vol. 48, No. 8. (2012), pp. 1133-1152, doi:10.1007/s10593-012-1116-x

Abstract

Methods for the preparation of 1-cyanoacetyl-3,5-dimethylpyrazole, its properties and application in organic synthesis are examined in detail for the first time. ...

 

Reactions of ketene aminals with n-arylmaleimides and dimethyl acetylenedicarboxylate, a direct pathway to derivatives of pyrrolo[1,2-a]imidazole and imidazo[1,2-a]pyridine

  [CiTO]
In Chemistry of Heterocyclic Compounds, Vol. 48, No. 8. (2012), pp. 1204-1212, doi:10.1007/s10593-012-1123-y

Abstract

The addition of N-arylmaleimides or dimethyl acetylenedicarboxylate to 2-imidazolideneacetophenones proceeds at the most nucleophilic carbon atom of the acetophenone derivatives and results in a rearrangement to give derivatives of 5-oxo-2,3,5,6-tetrahydro-1H-pyrrolo[1,2-a]imidazole or imidazo[1,2-a]pyridine, respectively. In the case of 2-imidazolidenecyclopentanones and 2-imidazolidine-cyclohexanones, the reaction terminates upon the addition of imide or dimethyl acetylenedicarboxylate at the nitrogen atom of the imidazoline system. ...

 

Benzyl-4,5-dihydroisoxazoles from benzylcyclo-propanes: regioselective insertion of an n=o fragment into the three-membered carbocycle of benzylcyclopropanes by the action of nitrous acid

  [CiTO]
In Chemistry of Heterocyclic Compounds, Vol. 48, No. 8. (2012), pp. 1220-1227, doi:10.1007/s10593-012-1125-9

Abstract

The action of equimolar amounts of nitrous acid formed in situ on benzylcyclopropanes with electron-donor and electron-withdrawing substituents in the aromatic part of the substrate lead, at certain temperatures, exclusively to the insertion of an N=O fragment into the three-membered carbocycle with subsequent formation of a heterocyclic isoxazoline (4,5-dihydroisoxazole) system. ...

 

Reactions of triazines and tetrazines with dienophiles (Review)

  [CiTO]
In Chemistry of Heterocyclic Compounds, Vol. 48, No. 8. (2012), pp. 1153-1176, doi:10.1007/s10593-012-1117-9

Abstract

Information on the development of a valuable synthetic methodology based on inverse electron-demand Diels–Alder reaction in the series of π-deficient azadienes (triazines and tetrazines) is summarized and classified. By this method it is possible to obtain mono-, di-, and triazines containing functional substituents both from the initial azine and from the dienophile. Such reactions are often the simplest and even the only possible method for the synthesis of substances with properties suitable for practical applications. ...

 

Synthesis of 6-alkyl-2-dialkylaminomethyl-7-hydroxy-3-(4-methylthiazol-2-yl)-4H-chromen-4-ones

  [CiTO]
In Chemistry of Heterocyclic Compounds, Vol. 48, No. 8. (2012), pp. 1181-1186, doi:10.1007/s10593-012-1119-7

Abstract

Amination of 6-alkyl-2-chloromethyl-7-hydroxy-3-(4-methylthiazol-2-yl)-4H-chromen-4-ones by secon-dary cyclic amines gives the corresponding 2-dialkylaminomethyl derivatives. ...

 

Synthesis of 1-aminonaphtho[1,2,3-cd]indol-6(2H)-ones

  [CiTO]
In Chemistry of Heterocyclic Compounds, Vol. 48, No. 8. (2012), pp. 1177-1180, doi:10.1007/s10593-012-1118-8

Abstract

A novel method has been developed for preparing N-substituted 1-aminonaphtho[1,2,3-cd]indol-6(2H)-ones by nucleophilic substitution of the nitro group in 1-nitronaphtho[1,2,3-cd]indol-6(2H)-ones. ...

 

4-hydroxy-2-quinolones. 203*. Reaction of 1-hexyl-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acid 4-pyridylmethylidene hydrazide with bromine

  [CiTO]
In Chemistry of Heterocyclic Compounds, Vol. 48, No. 8. (2012), pp. 1200-1203, doi:10.1007/s10593-012-1122-z

Abstract

It has been shown experimentally that upon the reaction of 1-hexyl-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acid 4-pyridylmethylidene hydrazide with molecular bromine in glacial acetic acid not only the azomethine carbon atom is brominated, but also the position 6 of the quinolone ring. ...

 

Direct C–C Coupling of Cyclic Aldonitrones with 1,2,4-Triazines Using S N H Reactions

  [CiTO]
In Chemistry of Heterocyclic Compounds, Vol. 48, No. 8. (2012), pp. 1213-1219, doi:10.1007/s10593-012-1124-x

Abstract

New nitrogen heterocyclic derivatives were obtained by a direct uncatalyzed by metals C–C cross-coupling of a cyclic aldonitrone lithium derivative with 1,2,4-triazines. ...

 

Preparation of N-phenylbenzo[h]quinolinium derivatives labeled with tritium

  [CiTO]
In Chemistry of Heterocyclic Compounds, Vol. 48, No. 8. (2012), pp. 1196-1199, doi:10.1007/s10593-012-1121-0

Abstract

The possibility of a direct phenylation of benzoquinoline nitrogen atom with nucleogenic phenyl cations has been demonstrated. A simple method has been developed for obtaining previously unknown tritium labeled N-phenyl derivatives of benzo[h]quinolinium, which are promising radioactive markers for studying the biological action mechanisms of medicinal substances containing the benzoquinolinium structure. ...

 

Substituted ureas based on 2,6-dimethyl-3,5-pyridinedicarboxylic acid azides

  [CiTO]
In Chemistry of Heterocyclic Compounds, Vol. 48, No. 8. (2012), pp. 1187-1195, doi:10.1007/s10593-012-1120-1

Abstract

Under Curtius rearrangement conditions, 2,6-dimethyl-3,5-pyridinedicarboxylic acid azides form the corresponding isocyanates which react in situ with ammonia, primary and secondary amines to form mono-, di-, and trisubstituted ureas. The reaction of the 5-ethoxycarbonyl-2,6-dimethylnicotinic acid azide with imidazole under these conditions gave symmetrical N,N'-bis[5-(ethoxycarbonyl)-2,6-di-methylpyridin-3-yl]ureas. ...

 

1-Cyanoacetyl-3,5-dimethylpyrazole – effective cyanoacetylating agent and a new building block for the synthesis of heterocyclic compounds (Review)

  [CiTO]
In Chemistry of Heterocyclic Compounds, Vol. 48, No. 8. (2012), pp. 1133-1152, doi:10.1007/s10593-012-1116-x

Abstract

Methods for the preparation of 1-cyanoacetyl-3,5-dimethylpyrazole, its properties and application in organic synthesis are examined in detail for the first time. ...

 

Reactions of ketene aminals with n-arylmaleimides and dimethyl acetylenedicarboxylate, a direct pathway to derivatives of pyrrolo[1,2-a]imidazole and imidazo[1,2-a]pyridine

  [CiTO]
In Chemistry of Heterocyclic Compounds, Vol. 48, No. 8. (2012), pp. 1204-1212, doi:10.1007/s10593-012-1123-y

Abstract

The addition of N-arylmaleimides or dimethyl acetylenedicarboxylate to 2-imidazolideneacetophenones proceeds at the most nucleophilic carbon atom of the acetophenone derivatives and results in a rearrangement to give derivatives of 5-oxo-2,3,5,6-tetrahydro-1H-pyrrolo[1,2-a]imidazole or imidazo[1,2-a]pyridine, respectively. In the case of 2-imidazolidenecyclopentanones and 2-imidazolidine-cyclohexanones, the reaction terminates upon the addition of imide or dimethyl acetylenedicarboxylate at the nitrogen atom of the imidazoline system. ...

 

Benzyl-4,5-dihydroisoxazoles from benzylcyclo-propanes: regioselective insertion of an n=o fragment into the three-membered carbocycle of benzylcyclopropanes by the action of nitrous acid

  [CiTO]
In Chemistry of Heterocyclic Compounds, Vol. 48, No. 8. (2012), pp. 1220-1227, doi:10.1007/s10593-012-1125-9

Abstract

The action of equimolar amounts of nitrous acid formed in situ on benzylcyclopropanes with electron-donor and electron-withdrawing substituents in the aromatic part of the substrate lead, at certain temperatures, exclusively to the insertion of an N=O fragment into the three-membered carbocycle with subsequent formation of a heterocyclic isoxazoline (4,5-dihydroisoxazole) system. ...

 

Reactions of triazines and tetrazines with dienophiles (Review)

  [CiTO]
In Chemistry of Heterocyclic Compounds, Vol. 48, No. 8. (2012), pp. 1153-1176, doi:10.1007/s10593-012-1117-9

Abstract

Information on the development of a valuable synthetic methodology based on inverse electron-demand Diels–Alder reaction in the series of π-deficient azadienes (triazines and tetrazines) is summarized and classified. By this method it is possible to obtain mono-, di-, and triazines containing functional substituents both from the initial azine and from the dienophile. Such reactions are often the simplest and even the only possible method for the synthesis of substances with properties suitable for practical applications. ...

 

Synthesis of 6-alkyl-2-dialkylaminomethyl-7-hydroxy-3-(4-methylthiazol-2-yl)-4H-chromen-4-ones

  [CiTO]
In Chemistry of Heterocyclic Compounds, Vol. 48, No. 8. (2012), pp. 1181-1186, doi:10.1007/s10593-012-1119-7

Abstract

Amination of 6-alkyl-2-chloromethyl-7-hydroxy-3-(4-methylthiazol-2-yl)-4H-chromen-4-ones by secon-dary cyclic amines gives the corresponding 2-dialkylaminomethyl derivatives. ...

 

Synthesis of 1-aminonaphtho[1,2,3-cd]indol-6(2H)-ones

  [CiTO]
In Chemistry of Heterocyclic Compounds, Vol. 48, No. 8. (2012), pp. 1177-1180, doi:10.1007/s10593-012-1118-8

Abstract

A novel method has been developed for preparing N-substituted 1-aminonaphtho[1,2,3-cd]indol-6(2H)-ones by nucleophilic substitution of the nitro group in 1-nitronaphtho[1,2,3-cd]indol-6(2H)-ones. ...

 

4-hydroxy-2-quinolones. 203*. Reaction of 1-hexyl-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acid 4-pyridylmethylidene hydrazide with bromine

  [CiTO]
In Chemistry of Heterocyclic Compounds, Vol. 48, No. 8. (2012), pp. 1200-1203, doi:10.1007/s10593-012-1122-z

Abstract

It has been shown experimentally that upon the reaction of 1-hexyl-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acid 4-pyridylmethylidene hydrazide with molecular bromine in glacial acetic acid not only the azomethine carbon atom is brominated, but also the position 6 of the quinolone ring. ...

 

Direct C–C Coupling of Cyclic Aldonitrones with 1,2,4-Triazines Using S N H Reactions

  [CiTO]
In Chemistry of Heterocyclic Compounds, Vol. 48, No. 8. (2012), pp. 1213-1219, doi:10.1007/s10593-012-1124-x

Abstract

New nitrogen heterocyclic derivatives were obtained by a direct uncatalyzed by metals C–C cross-coupling of a cyclic aldonitrone lithium derivative with 1,2,4-triazines. ...

 

Preparation of N-phenylbenzo[h]quinolinium derivatives labeled with tritium

  [CiTO]
In Chemistry of Heterocyclic Compounds, Vol. 48, No. 8. (2012), pp. 1196-1199, doi:10.1007/s10593-012-1121-0

Abstract

The possibility of a direct phenylation of benzoquinoline nitrogen atom with nucleogenic phenyl cations has been demonstrated. A simple method has been developed for obtaining previously unknown tritium labeled N-phenyl derivatives of benzo[h]quinolinium, which are promising radioactive markers for studying the biological action mechanisms of medicinal substances containing the benzoquinolinium structure. ...

 

Substituted ureas based on 2,6-dimethyl-3,5-pyridinedicarboxylic acid azides

  [CiTO]
In Chemistry of Heterocyclic Compounds, Vol. 48, No. 8. (2012), pp. 1187-1195, doi:10.1007/s10593-012-1120-1

Abstract

Under Curtius rearrangement conditions, 2,6-dimethyl-3,5-pyridinedicarboxylic acid azides form the corresponding isocyanates which react in situ with ammonia, primary and secondary amines to form mono-, di-, and trisubstituted ureas. The reaction of the 5-ethoxycarbonyl-2,6-dimethylnicotinic acid azide with imidazole under these conditions gave symmetrical N,N'-bis[5-(ethoxycarbonyl)-2,6-di-methylpyridin-3-yl]ureas. ...

 

1-Cyanoacetyl-3,5-dimethylpyrazole – effective cyanoacetylating agent and a new building block for the synthesis of heterocyclic compounds (Review)

  [CiTO]
In Chemistry of Heterocyclic Compounds, Vol. 48, No. 8. (2012), pp. 1133-1152, doi:10.1007/s10593-012-1116-x

Abstract

Methods for the preparation of 1-cyanoacetyl-3,5-dimethylpyrazole, its properties and application in organic synthesis are examined in detail for the first time. ...

 

Reactions of ketene aminals with n-arylmaleimides and dimethyl acetylenedicarboxylate, a direct pathway to derivatives of pyrrolo[1,2-a]imidazole and imidazo[1,2-a]pyridine

  [CiTO]
In Chemistry of Heterocyclic Compounds, Vol. 48, No. 8. (2012), pp. 1204-1212, doi:10.1007/s10593-012-1123-y

Abstract

The addition of N-arylmaleimides or dimethyl acetylenedicarboxylate to 2-imidazolideneacetophenones proceeds at the most nucleophilic carbon atom of the acetophenone derivatives and results in a rearrangement to give derivatives of 5-oxo-2,3,5,6-tetrahydro-1H-pyrrolo[1,2-a]imidazole or imidazo[1,2-a]pyridine, respectively. In the case of 2-imidazolidenecyclopentanones and 2-imidazolidine-cyclohexanones, the reaction terminates upon the addition of imide or dimethyl acetylenedicarboxylate at the nitrogen atom of the imidazoline system. ...

 

Benzyl-4,5-dihydroisoxazoles from benzylcyclo-propanes: regioselective insertion of an n=o fragment into the three-membered carbocycle of benzylcyclopropanes by the action of nitrous acid

  [CiTO]
In Chemistry of Heterocyclic Compounds, Vol. 48, No. 8. (2012), pp. 1220-1227, doi:10.1007/s10593-012-1125-9

Abstract

The action of equimolar amounts of nitrous acid formed in situ on benzylcyclopropanes with electron-donor and electron-withdrawing substituents in the aromatic part of the substrate lead, at certain temperatures, exclusively to the insertion of an N=O fragment into the three-membered carbocycle with subsequent formation of a heterocyclic isoxazoline (4,5-dihydroisoxazole) system. ...

 

Reactions of triazines and tetrazines with dienophiles (Review)

  [CiTO]
In Chemistry of Heterocyclic Compounds, Vol. 48, No. 8. (2012), pp. 1153-1176, doi:10.1007/s10593-012-1117-9

Abstract

Information on the development of a valuable synthetic methodology based on inverse electron-demand Diels–Alder reaction in the series of π-deficient azadienes (triazines and tetrazines) is summarized and classified. By this method it is possible to obtain mono-, di-, and triazines containing functional substituents both from the initial azine and from the dienophile. Such reactions are often the simplest and even the only possible method for the synthesis of substances with properties suitable for practical applications. ...

 

Synthesis of 6-alkyl-2-dialkylaminomethyl-7-hydroxy-3-(4-methylthiazol-2-yl)-4H-chromen-4-ones

  [CiTO]
In Chemistry of Heterocyclic Compounds, Vol. 48, No. 8. (2012), pp. 1181-1186, doi:10.1007/s10593-012-1119-7

Abstract

Amination of 6-alkyl-2-chloromethyl-7-hydroxy-3-(4-methylthiazol-2-yl)-4H-chromen-4-ones by secon-dary cyclic amines gives the corresponding 2-dialkylaminomethyl derivatives. ...

 

Synthesis of 1-aminonaphtho[1,2,3-cd]indol-6(2H)-ones

  [CiTO]
In Chemistry of Heterocyclic Compounds, Vol. 48, No. 8. (2012), pp. 1177-1180, doi:10.1007/s10593-012-1118-8

Abstract

A novel method has been developed for preparing N-substituted 1-aminonaphtho[1,2,3-cd]indol-6(2H)-ones by nucleophilic substitution of the nitro group in 1-nitronaphtho[1,2,3-cd]indol-6(2H)-ones. ...

 

4-hydroxy-2-quinolones. 203*. Reaction of 1-hexyl-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acid 4-pyridylmethylidene hydrazide with bromine

  [CiTO]
In Chemistry of Heterocyclic Compounds, Vol. 48, No. 8. (2012), pp. 1200-1203, doi:10.1007/s10593-012-1122-z

Abstract

It has been shown experimentally that upon the reaction of 1-hexyl-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acid 4-pyridylmethylidene hydrazide with molecular bromine in glacial acetic acid not only the azomethine carbon atom is brominated, but also the position 6 of the quinolone ring. ...

 

Direct C–C Coupling of Cyclic Aldonitrones with 1,2,4-Triazines Using S N H Reactions

  [CiTO]
In Chemistry of Heterocyclic Compounds, Vol. 48, No. 8. (2012), pp. 1213-1219, doi:10.1007/s10593-012-1124-x

Abstract

New nitrogen heterocyclic derivatives were obtained by a direct uncatalyzed by metals C–C cross-coupling of a cyclic aldonitrone lithium derivative with 1,2,4-triazines. ...

 

Preparation of N-phenylbenzo[h]quinolinium derivatives labeled with tritium

  [CiTO]
In Chemistry of Heterocyclic Compounds, Vol. 48, No. 8. (2012), pp. 1196-1199, doi:10.1007/s10593-012-1121-0

Abstract

The possibility of a direct phenylation of benzoquinoline nitrogen atom with nucleogenic phenyl cations has been demonstrated. A simple method has been developed for obtaining previously unknown tritium labeled N-phenyl derivatives of benzo[h]quinolinium, which are promising radioactive markers for studying the biological action mechanisms of medicinal substances containing the benzoquinolinium structure. ...

 

Substituted ureas based on 2,6-dimethyl-3,5-pyridinedicarboxylic acid azides

  [CiTO]
In Chemistry of Heterocyclic Compounds, Vol. 48, No. 8. (2012), pp. 1187-1195, doi:10.1007/s10593-012-1120-1

Abstract

Under Curtius rearrangement conditions, 2,6-dimethyl-3,5-pyridinedicarboxylic acid azides form the corresponding isocyanates which react in situ with ammonia, primary and secondary amines to form mono-, di-, and trisubstituted ureas. The reaction of the 5-ethoxycarbonyl-2,6-dimethylnicotinic acid azide with imidazole under these conditions gave symmetrical N,N'-bis[5-(ethoxycarbonyl)-2,6-di-methylpyridin-3-yl]ureas. ...

 

1-Cyanoacetyl-3,5-dimethylpyrazole – effective cyanoacetylating agent and a new building block for the synthesis of heterocyclic compounds (Review)

  [CiTO]
In Chemistry of Heterocyclic Compounds, Vol. 48, No. 8. (2012), pp. 1133-1152, doi:10.1007/s10593-012-1116-x

Abstract

Methods for the preparation of 1-cyanoacetyl-3,5-dimethylpyrazole, its properties and application in organic synthesis are examined in detail for the first time. ...

 

Reactions of ketene aminals with n-arylmaleimides and dimethyl acetylenedicarboxylate, a direct pathway to derivatives of pyrrolo[1,2-a]imidazole and imidazo[1,2-a]pyridine

  [CiTO]
In Chemistry of Heterocyclic Compounds, Vol. 48, No. 8. (2012), pp. 1204-1212, doi:10.1007/s10593-012-1123-y

Abstract

The addition of N-arylmaleimides or dimethyl acetylenedicarboxylate to 2-imidazolideneacetophenones proceeds at the most nucleophilic carbon atom of the acetophenone derivatives and results in a rearrangement to give derivatives of 5-oxo-2,3,5,6-tetrahydro-1H-pyrrolo[1,2-a]imidazole or imidazo[1,2-a]pyridine, respectively. In the case of 2-imidazolidenecyclopentanones and 2-imidazolidine-cyclohexanones, the reaction terminates upon the addition of imide or dimethyl acetylenedicarboxylate at the nitrogen atom of the imidazoline system. ...

 

Benzyl-4,5-dihydroisoxazoles from benzylcyclo-propanes: regioselective insertion of an n=o fragment into the three-membered carbocycle of benzylcyclopropanes by the action of nitrous acid

  [CiTO]
In Chemistry of Heterocyclic Compounds, Vol. 48, No. 8. (2012), pp. 1220-1227, doi:10.1007/s10593-012-1125-9

Abstract

The action of equimolar amounts of nitrous acid formed in situ on benzylcyclopropanes with electron-donor and electron-withdrawing substituents in the aromatic part of the substrate lead, at certain temperatures, exclusively to the insertion of an N=O fragment into the three-membered carbocycle with subsequent formation of a heterocyclic isoxazoline (4,5-dihydroisoxazole) system. ...

 

Reactions of triazines and tetrazines with dienophiles (Review)

  [CiTO]
In Chemistry of Heterocyclic Compounds, Vol. 48, No. 8. (2012), pp. 1153-1176, doi:10.1007/s10593-012-1117-9

Abstract

Information on the development of a valuable synthetic methodology based on inverse electron-demand Diels–Alder reaction in the series of π-deficient azadienes (triazines and tetrazines) is summarized and classified. By this method it is possible to obtain mono-, di-, and triazines containing functional substituents both from the initial azine and from the dienophile. Such reactions are often the simplest and even the only possible method for the synthesis of substances with properties suitable for practical applications. ...

 

Synthesis of 6-alkyl-2-dialkylaminomethyl-7-hydroxy-3-(4-methylthiazol-2-yl)-4H-chromen-4-ones

  [CiTO]
In Chemistry of Heterocyclic Compounds, Vol. 48, No. 8. (2012), pp. 1181-1186, doi:10.1007/s10593-012-1119-7

Abstract

Amination of 6-alkyl-2-chloromethyl-7-hydroxy-3-(4-methylthiazol-2-yl)-4H-chromen-4-ones by secon-dary cyclic amines gives the corresponding 2-dialkylaminomethyl derivatives. ...

 

Synthesis of 1-aminonaphtho[1,2,3-cd]indol-6(2H)-ones

  [CiTO]
In Chemistry of Heterocyclic Compounds, Vol. 48, No. 8. (2012), pp. 1177-1180, doi:10.1007/s10593-012-1118-8

Abstract

A novel method has been developed for preparing N-substituted 1-aminonaphtho[1,2,3-cd]indol-6(2H)-ones by nucleophilic substitution of the nitro group in 1-nitronaphtho[1,2,3-cd]indol-6(2H)-ones. ...

 

4-hydroxy-2-quinolones. 203*. Reaction of 1-hexyl-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acid 4-pyridylmethylidene hydrazide with bromine

  [CiTO]
In Chemistry of Heterocyclic Compounds, Vol. 48, No. 8. (2012), pp. 1200-1203, doi:10.1007/s10593-012-1122-z

Abstract

It has been shown experimentally that upon the reaction of 1-hexyl-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acid 4-pyridylmethylidene hydrazide with molecular bromine in glacial acetic acid not only the azomethine carbon atom is brominated, but also the position 6 of the quinolone ring. ...

 

Direct C–C Coupling of Cyclic Aldonitrones with 1,2,4-Triazines Using S N H Reactions

  [CiTO]
In Chemistry of Heterocyclic Compounds, Vol. 48, No. 8. (2012), pp. 1213-1219, doi:10.1007/s10593-012-1124-x

Abstract

New nitrogen heterocyclic derivatives were obtained by a direct uncatalyzed by metals C–C cross-coupling of a cyclic aldonitrone lithium derivative with 1,2,4-triazines. ...

 

Preparation of N-phenylbenzo[h]quinolinium derivatives labeled with tritium

  [CiTO]
In Chemistry of Heterocyclic Compounds, Vol. 48, No. 8. (2012), pp. 1196-1199, doi:10.1007/s10593-012-1121-0

Abstract

The possibility of a direct phenylation of benzoquinoline nitrogen atom with nucleogenic phenyl cations has been demonstrated. A simple method has been developed for obtaining previously unknown tritium labeled N-phenyl derivatives of benzo[h]quinolinium, which are promising radioactive markers for studying the biological action mechanisms of medicinal substances containing the benzoquinolinium structure. ...

 

Substituted ureas based on 2,6-dimethyl-3,5-pyridinedicarboxylic acid azides

  [CiTO]
In Chemistry of Heterocyclic Compounds, Vol. 48, No. 8. (2012), pp. 1187-1195, doi:10.1007/s10593-012-1120-1

Abstract

Under Curtius rearrangement conditions, 2,6-dimethyl-3,5-pyridinedicarboxylic acid azides form the corresponding isocyanates which react in situ with ammonia, primary and secondary amines to form mono-, di-, and trisubstituted ureas. The reaction of the 5-ethoxycarbonyl-2,6-dimethylnicotinic acid azide with imidazole under these conditions gave symmetrical N,N'-bis[5-(ethoxycarbonyl)-2,6-di-methylpyridin-3-yl]ureas. ...

 

1-Cyanoacetyl-3,5-dimethylpyrazole – effective cyanoacetylating agent and a new building block for the synthesis of heterocyclic compounds (Review)

  [CiTO]
In Chemistry of Heterocyclic Compounds, Vol. 48, No. 8. (2012), pp. 1133-1152, doi:10.1007/s10593-012-1116-x

Abstract

Methods for the preparation of 1-cyanoacetyl-3,5-dimethylpyrazole, its properties and application in organic synthesis are examined in detail for the first time. ...

 

Synthesis of novel 1,2,3,6-tetraazapyrene heterocyclic system representatives – 3,8-dihydropyrido[2',3',4':4,5]naphtho-[1,8-<i>de</i>][1,2,3]triazin-7(6<i>H</i>)-ones

  [CiTO]
Chemistry of Heterocyclic Compounds (8 November 2012), pp. 1-3, doi:10.1007/s10593-012-1132-x
 

Unusual reaction of 1<i>H</i>-perimidines with sodium azide and benzoyl hydrazine in polyphosphoric acid

  [CiTO]
Chemistry of Heterocyclic Compounds (8 November 2012), pp. 1-3, doi:10.1007/s10593-012-1133-9
 

A novel route for the preparation of chromenoquinazolines

  [CiTO]
Chemistry of Heterocyclic Compounds (8 November 2012), pp. 1-3, doi:10.1007/s10593-012-1134-8

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