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Synthesis of Some New Spiro, Isolated and Fused Heterocycles Based on 1 H ‐indole‐2‐One
Author(s) -
ElEmary T. I.,
Ahmed R. A.,
Bakhite E. A.
Publication year - 2001
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.200100134
Subject(s) - chemistry , hydrazone , indole test , hydrazine (antidepressant) , malononitrile , hydrate , methylene , thioglycolic acid , medicinal chemistry , triethyl orthoformate , organic chemistry , chloride , catalysis , chromatography
Abstract The reaction of 3‐benzoylcyanomethylidine‐1( H )‐indole‐2‐one ( 1 ) with a variety of active methylene compounds, thioglycolic acid, glycine, hydrazine hydrate and phenyl hydrazine led to the formation of compounds 4a‐d‐10 . 3‐Thiosemicarbazide‐1( H )‐indole‐2‐one 2 on reaction with α‐halocarbonyl compounds gave compounds 11a‐c, 12a‐c . The latter compounds on heating with phosphoryl chloride, cyclization takes place via losing water to give the angular tetracyclic compounds 13a,b and 14a‐c . Cyanoacetic hydrazone derivative 3 readily cyclized upon heating in triethyl orthoformate to give the tricyclic system, oxopyridazino indole 15 . On the other hand, the reaction of 3 with benzylidine malononitrile and benzylidene ethylcyanoactate gave the pyranyl hydrazone derivatives 16a,b .