New tandem cyclo‐ and/or addition reactions between <i>N</i>‐arylisoindolines with benzyne and dimethyl acetylenedicarboxylate

1,4‐Disubstituted thiosemicarbazides reacted with dimethyl acetylenedicarboxylate with formation of (2‐hydrazono‐4‐oxothiazolidin‐5‐ylidene)acetates and, in one case, a (2‐imino‐1,3,4‐thiadiazin‐5‐on‐6‐ylidene)acetate. Several mechanistic options involving nucleophilic interaction are presented. The structures of all newly synthesized compounds were identified by 1H NMR, 13C NMR, COSY, HMQC and HMBC spectral data.

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Tetracyanoethene and 1‐Amino‐1,2,2‐ethenetricarbonitrile in the Synthesis of Heterocycles of Prospective Antioxidant and Antibacterial

Aly

Malah

Ishak

et al. 2016

Journal of Heterocyclic Chem

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Reaction of 1,1,2,2‐ethenetetracarbonitrile (TCNE) with aroyl thioureas in dioxane catalyzed by few drops of piperidine, led to the corresponding 1,2,4‐oxathiazoles. Under the same reaction condition, thiosemicarbazide or thiosemicarbazone reacted with either TCNE or 1‐amino‐1,2,2‐ethene‐tricarbonitrile. The structures of the products were elucidated via NMR, IR, mass spectra, and elemental analyses. The mechanism of formation was discussed. Biological (against Gram‐positive and Gram‐negative bacteria) and antioxidant activities were tested. Some of these heterocyclic compounds showed high activity as antioxidant and antibacterial compounds. The structure–activity relationship was investigated.

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New tandem cyclo‐ and/or addition reactions between N‐arylisoindolines with benzyne and dimethyl acetylenedicarboxylate

Cited by 19 publications

References 24 publications

ChemInform Abstract: New Tandem Cyclo‐ and/or Addition Reactions Between N‐Arylisoindolines with Benzyne and Dimethyl Acetylenedicarboxylate.

ChemInform Abstract: New Tandem Cyclo‐ and/or Addition Reactions Between N‐Arylisoindolines with Benzyne and Dimethyl Acetylenedicarboxylate.

A Facile Method for the Synthesis of Hydrazine‐4‐oxothiazolidine and Imino‐5‐oxothiadiazine Derivatives from 1,4‐Disubstituted Thiosemicarbazides

Tetracyanoethene and 1‐Amino‐1,2,2‐ethenetricarbonitrile in the Synthesis of Heterocycles of Prospective Antioxidant and Antibacterial

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