The Synthesis of (4<i>E</i>
)-<i>N</i>
-(4-chlorophenyl)-5-substituted-2-diazo-3-oxopent-4-enoic Acid Amides

He, Dong; Wang, Dongdong; Jin, Chi-Qiong

doi:10.1002/jccs.200500141

Jnl Chinese Chemical Soc

2005

DOI: 10.1002/jccs.200500141

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The Synthesis of (4E )-N -(4-chlorophenyl)-5-substituted-2-diazo-3-oxopent-4-enoic Acid Amides

Dong He

Dongdong Wang

Chi-Qiong Jin

Abstract: acid amides 5a~j were synthesized with N-(4-chlorophenyl)-2-diazo-3-oxobutyramide 4 from p-chloroaniline and various arylaldehydes. The yielded products 5a~j were investigated with NMR, MS, IR, and X-ray crystallographic techniques.

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Cited by 5 publications

References 19 publications

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Tandem Michael addition/imino‐nitrile cyclization synthesis of 2‐amino‐6‐(1‐aryl‐5‐methyl‐1H‐1,2,3‐triazol‐4yl)‐4‐phenylpyridine‐3‐carbonitrile

Wang

Gao

et al. 2010

Journal of Heterocyclic Chem

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in Wiley InterScience (www.interscience.wiley.com).Several 2-amino-6-(1-aryl-5-methyl-1H-1,2,3-triazol-4-yl)-4-phenylpyridine-3-carbonitrile have been synthesized by Tandem Michael addition/imino-nitrile cyclization and the structures of these compounds were established by MS, IR, CHN, and 1 H NMR spectral data. The crystal structure of 2-amino-6-[1-(4-methoxyphenyl)-5-methyl-1H-1,2,3-triazol-4-yl]-4-phenylpyridine-3-carbonitrile was established by X-ray diffraction.

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Tandem Michael addition/imino‐nitrile cyclization synthesis of 2‐amino‐6‐(1‐aryl‐5‐methyl‐1H‐1,2,3‐triazol‐4yl)‐4‐phenylpyridine‐3‐carbonitrile

Wang

Gao

et al. 2010

Journal of Heterocyclic Chem

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An efficient synthesis of 5‐aryl‐4,5‐dihydro‐3‐(5‐methyl‐1‐p‐tolyl‐1H‐1,2,3‐triazol‐4‐yl)‐1‐(4‐phenylthiazol‐2‐yl)pyrazoles

Dong

Cui

Gao

et al. 2011

Journal of Heterocyclic Chem

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Some new target products 5‐aryl‐4,5‐dihydro‐3‐(5‐methyl‐1‐p‐tolyl‐1H‐1,2,3‐triazol‐4‐yl)‐1‐(4‐phenylthiazol‐2‐yl)pyrazoles 5a, 5b, 5c, 5d, 5e, 5f, 5g, 5h, 5i, 5j have been synthesized by reaction of 2‐bromo‐1‐phenylethanone and compounds 4a, 4b, 4c, 4d, 4e, 4f, 4g, 4h, 4i, 4j which were prepared from the combination of thiosemicarbazide and (E)‐3‐aryl‐1‐(5‐methyl‐1‐p‐tolyl‐1H‐1,2,3‐triazol‐4‐yl)‐prop‐2‐en‐1‐ones 3a, 3b, 3c, 3d, 3e, 3f, 3g, 3h, 3i, 3j. All the structures were established by MS, IR, CHN, and 1H NMR spectra data. Synthesis of structure diversity is applied. J. Heterocyclic Chem., (2011).

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A Novel Base‐Solvent Controlled Chemoselective Azide Attack on an Ester Group versus Keto in Alkyl 3‐Substituted 3‐Oxopropanoates: Mechanistic Insights

et al. 2017

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During the exploration of arylazides reactions with alkyl 3‐substituted‐3‐oxopropanoates under the Dimroth reaction conditions (MeONa‐MeOH) azide attack on ester group versus keto was found out in few examples yielding stable 3‐alkyl‐2‐diazo‐3‐oxo‐N‐(aryl)propanamides instead of obvious target 1‐aryl‐5‐alkyl‐1H‐1,2,3‐triazole‐4‐carboxylic acids. The formation of diazocompounds was observed in case of 3‐(4,4‐diethoxymethyl)‐, isopropyl‐, cyclopropyl‐3‐oxopropanoate in the reaction with arylazides, especially, those containing electro‐withdrawing substituents. Influence of the base‐solvent system on diazo products yields was investigated and mechanistic insights of Dimroth reaction were discussed.

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The Synthesis of (4E )-N -(4-chlorophenyl)-5-substituted-2-diazo-3-oxopent-4-enoic Acid Amides

Abstract: acid amides 5a~j were synthesized with N-(4-chlorophenyl)-2-diazo-3-oxobutyramide 4 from p-chloroaniline and various arylaldehydes. The yielded products 5a~j were investigated with NMR, MS, IR, and X-ray crystallographic techniques.

Cited by 5 publications

References 19 publications

Tandem Michael addition/imino‐nitrile cyclization synthesis of 2‐amino‐6‐(1‐aryl‐5‐methyl‐1H‐1,2,3‐triazol‐4yl)‐4‐phenylpyridine‐3‐carbonitrile

Tandem Michael addition/imino‐nitrile cyclization synthesis of 2‐amino‐6‐(1‐aryl‐5‐methyl‐1H‐1,2,3‐triazol‐4yl)‐4‐phenylpyridine‐3‐carbonitrile

An efficient synthesis of 5‐aryl‐4,5‐dihydro‐3‐(5‐methyl‐1‐p‐tolyl‐1H‐1,2,3‐triazol‐4‐yl)‐1‐(4‐phenylthiazol‐2‐yl)pyrazoles

A Novel Base‐Solvent Controlled Chemoselective Azide Attack on an Ester Group versus Keto in Alkyl 3‐Substituted 3‐Oxopropanoates: Mechanistic Insights

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