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3-(phenylhydrazono)-indan-1-one and 2-dimethylaminomethylene-3-(phenylhydrazono)-indan-1-one as useful synthons for the construction of new heterocyclic systems

✍ Scribed by Tarek M. Abu Elmaati; Samy B. Said; Nahla S. Abu Elenein; Nabiel M. Khodeir; Mamdouh M. Sofan

Publisher: Journal of Heterocyclic Chemistry
Year: 2003
Tongue: English
Weight: 57 KB
Volume: 40
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570400312

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✦ Synopsis

Abstract

The hydrazone 1 reacts with DMFDMA to give 2‐dimethylaminomethylene‐3‐(phenylhydrazono)‐indan‐1‐one (2) which reacts with hydrazine hydrate and the pyrazole derivative 4 to afford the indenopyrazole derivatives 3 and the indenofluorene 5 respectively. The reaction of 2 with the active methylene compounds, mainly malononitrile, cyanoacetamide and malononitrile dimer was investigated and found to proceed successfully to yield the indenopyran 7, indenpyridine 8b and trinitrile 9 respectively. Compound 2 reacted with l__H__‐benzimidazole‐2‐acetonitrile 10 to give to the diazaindenofluorene derivative 11. Also, 2 reacted with ω‐cyano compounds 12a,b to afford the indenopyran 14. On the other hand the hydrazone 1 was allowed to react with the enaminones 15, 18 and 21 affording the diazabenzoazulene derivatives 17, 20 and the indeno[1,2‐b]pyridin 23, respectively.

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