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1,3-Dicarboxybenzannulation of acyl systems via a one-pot Michael-Michael-intramolecular aldol-dehydration reaction sequence

Srikrishna, A and Sharma, Veera Raghava G (1993) 1,3-Dicarboxybenzannulation of acyl systems via a one-pot Michael-Michael-intramolecular aldol-dehydration reaction sequence. In: Indian Journal of Chemistry - Section B: Organic and Medicinal Chemistry, 32B (8). pp. 832-837.

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Abstract

Reaction of the 3-lithio derivative of Me propynoate with 4-methylcyclohex-3-en-1-one (3) (or the lithium dienolate 6 of the enone 3 with Me propynoate), contrary to the expected addition product 1, generated the dihydronaphthalene derivative I, via a sequential Michael, Michael, intramolecular aldol and dehydration reactions. Oxidation with DDQ transformed the dihydronaphthalene I into the naphthalene derivative confirming the structure of I. Generality of this new, one-pot, three component meta-dimethoxycarbonylbenzannulation is established by the annulation of other Michael donors 10, 12-15, resulting in the aromatic products 11, 16-19.

Item Type: Journal Article
Additional Information: Copyright of this article belonogs to Council of Scientific & Industrial Research.
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 20 Jun 2008
Last Modified: 27 Aug 2008 13:30
URI: http://eprints.iisc.ernet.in/id/eprint/14634

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