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

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 comp...

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Bibliographic Details
Published in:Journal of heterocyclic chemistry 2003-05, Vol.40 (3), p.481-486
Main Authors: Abu Elmaati, Tarek M., Said, Samy B., Abu Elenein, Nahla S., Khodeir, Nabiel M., Sofan, Mamdouh M.
Format: Article
Language:English
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Summary: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 lH‐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.
ISSN:0022-152X
1943-5193
DOI:10.1002/jhet.5570400312