Heteroannulation of chromene derivatives. Synthesis of chromeno[4,3- e ] indazolone chromeno[4,3- f ]quinazoline and pyrano[3,2- c ]chromene derivatives

Pentane-2,4-dione and 3-ethoxycarbonylcoumarin react in the presence of sodium ethoxide to form 10-acetyl-7,9-dihydroxy-6 H-benzo[ c]chromen-6-one (2). Compound 2 reacted with aromatic aldehydes and ethyl cyanoacetate to give the chromeno-chromenediones 3 and 4 respectively, with hydrazine hydrate t...

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Published in:Journal of chemical research 2009-01, Vol.2009 (1), p.41-45
Main Authors: Mahmoud, Mahmoud R, El-Bassiouny, Fakhry A, Azab, Mohamed E, El-Kady, Mohamed Y, Rashed, Hesham M
Format: Article
Language:English
Subjects:
Chemical reactions
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Summary:Pentane-2,4-dione and 3-ethoxycarbonylcoumarin react in the presence of sodium ethoxide to form 10-acetyl-7,9-dihydroxy-6 H-benzo[ c]chromen-6-one (2). Compound 2 reacted with aromatic aldehydes and ethyl cyanoacetate to give the chromeno-chromenediones 3 and 4 respectively, with hydrazine hydrate to form the azine 5, with phenyl hydrazine giving the chromeno-indazole 6, with primary amines to form the imines 7a–f, and with thiourea to give the chromeno-quinazoline 8. Methyl 2-amino-4-(4-methoxyphenyl)-5-oxo-4,5-dihydro-pyrano[3,2- c]chromene-3-carboxylate (9a) and the corresponding 3-carbonitrile 9b were prepared, and the reactions of the ester 9a with phenacyl chloride, furoyl chloride, and hydrazine hydrate were investigated.
ISSN:1747-5198
2047-6507
DOI:10.3184/030823409X393727