Synthesis of 2‐Aryl‐5‐oxo‐4‐[2‐(phenylmethylidene)hydrazino]‐2,5‐dihydro‐1H‐pyrrole‐3‐carboxylates by the Reaction between Hydrazones,Acetylenedicarboxylates, and 1‐Aryl‐N,N′‐bis(arylmethylidene)methanediamines |
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| Authors: | Abdolali Alizadeh Vahid Saberi Javad Mokhtari |
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| Institution: | 1. Department of Chemistry, Tarbiat Modares University, P.O. Box 14115‐175, Tehran, Iran, (phone: +98‐21‐88006631;2. fax: +98‐21‐88006544) |
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| Abstract: | An efficient approach for the preparation of functionalized 2‐aryl‐2,5‐dihydro‐5‐oxo‐4‐2‐(phenylmethylidene)hydrazino]‐1H‐pyrroles is described. The four‐component reaction between aldehydes, NH2NH2?H2O, dialkyl acetylenedicarboxylates, and 1‐aryl‐N,N′‐bis(arylmethylidene)methanediamines proceeds in EtOH under reflux in good‐to‐excellent yields (Scheme 1). The structures of 4 were corroborated spectroscopically (IR, 1H‐ and 13C‐NMR, and EI‐MS, and, in the case of 4f , by X‐ray crystallography). A plausible mechanism for this type of reaction is proposed (Scheme 2). |
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| Keywords: | Hydrazine hydrate Aldehydes Acetylenedicarboxylates dialkyl Methanediamine 1‐aryl‐N N′ ‐bis(arylmethylidene)‐ Multicomponent reactions |
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