Condensation Reaction Between α-Amino Acid Phenylhydrazides and Carbonyl Compounds

✍ Scribed by Giancarlo Verardo; Paola Geatti; Paolo Martinuzzi; Marcello Merli; Nicoletta Toniutti

• Book ID: 102177230
• Publisher: John Wiley and Sons
• Year: 2003
• Tongue: English
• Weight: 178 KB
• Volume: 2003
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/ejoc.200300251

✦ Synopsis

Abstract

The natural α‐amino acid phenylhydrazides 1a−d readily react with the aldehydes 2a−d and ketones 2e−h to produce the 3‐(phenylamino)imidazolidin‐4‐one derivatives 4 in good yields. Their structures were confirmed by X‐ray structural analysis. Polycyclic systems were obtained from the reaction of L‐tryptophan phenylhydrazide (1d) and L‐histidine phenylhydrazide (1e) with benzaldehyde (2c), which gave 1,10‐diphenyl‐2‐(phenylamino)‐2,9,10a‐triazacyclopenta[b]fluoren‐3‐one (5dc) and 4,6‐diphenyl‐7‐(phenylamino)‐3,4,6,7,8a,9‐hexahydro‐8__H__‐diimidazo[1,5‐a:4′,5′‐d]pyridin‐8‐one (5ec), respectively. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)