[4 + 2] cycloaromatization of 4-bis(methylthio)-3-buten-2-one with active methylene ketones: a simple and facile phenol annulation

Barun, Okram ; Nandi, Sukumar ; Panda, Kausik ; Ila, Hiriyakkanavar ; Junjappa, Hiriyakkanavar (2002) [4 + 2] cycloaromatization of 4-bis(methylthio)-3-buten-2-one with active methylene ketones: a simple and facile phenol annulation Journal of Organic Chemistry, 67 (15). pp. 5398-5401. ISSN 0022-3263

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Official URL: http://pubs.acs.org/doi/abs/10.1021/jo020219r

Related URL: http://dx.doi.org/10.1021/jo020219r

Abstract

A new method for β-phenol annulation involving base-induced [4C + 2C] cycloaromatization of readily available 4-bis(methylthio)-3-buten-2-one with a variety of cyclic and acyclic active methylene ketones has been reported. Appropriate choice of ketones allows synthesis of diverse frameworks such as dihydroindan, tetrahydronaphthalenes, their higher homologues, dihydro/octahydrophenanthrenes, anthracene, and heteroannulated analogue in high yields with regiocontrol of phenolic functionality.

Item Type:Article
Source:Copyright of this article belongs to American Chemical Society.
ID Code:15313
Deposited On:13 Nov 2010 12:57
Last Modified:22 Feb 2011 06:20

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