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Behavior of 3-benzylamino-5-aryl-2(3H)-furanones towards some nitrogen nucleophiles

✍ Scribed by Kamal A. Kandeel; Ahmed S. A. Youssef; Wael S. I. Abou-Elmagd; Ahmed I. Hashem

Publisher
Journal of Heterocyclic Chemistry
Year
2006
Tongue
English
Weight
97 KB
Volume
43
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

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Ring closure of 2‐N‐benzylamino‐3‐aroylpropionic acids (3) with acetic anhydride afforded 3‐N‐benzylamino‐5‐aryl‐2(3__H__)‐furanones (4). The reaction of the furanones (4) with benzylamine in benzene was found to be time dependent. Thus refluxing the reaction mixture for 1 h only afforded the open‐chain amides (5a‐c). When the reaction was conducted for 3 h the 2(3__H__)‐pyrrolones (6) were obtained. Hydrazine hydrate affected ring opening of the furanones to give the hydrazides (5d‐f). Also, semicarbazide converted (4) into the corresponding semicarbazide derivatives (5g‐i). The hydrazides (5d‐f) were reacted with benzoyl chloride to give the corresponding diaroylhydrazines (5j‐l). The open‐chain derivatives (5) were converted into a variety of heterocycles: isothiazolones (7), dihydropyridazinones (8), 1,3,4‐oxadiazoles (9) and 1,2,4‐triazole derivatives (10) via cyclization reactions.

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