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Behavior of 3‐benzylamino‐5‐aryl‐2(3 H )‐furanones towards some nitrogen nucleophiles
Author(s) -
Kandeel Kamal A.,
Youssef Ahmed S. A.,
AbouElmagd Wael S. I.,
Hashem Ahmed I.
Publication year - 2006
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570430422
Subject(s) - chemistry , benzylamine , semicarbazide , hydrazine (antidepressant) , medicinal chemistry , ring (chemistry) , benzene , acetic anhydride , aryl , nucleophile , hydrate , pyridine , morpholine , chloride , organic chemistry , catalysis , alkyl , chromatography
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.