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Synthesis 2008(11): 1798-1804  
DOI: 10.1055/s-2008-1072580
PAPER
© Georg Thieme Verlag Stuttgart · New York

A Furan Recyclization Reaction as a New Approach to Isochromenes

Alexander V. Butin*a, Vladimir T. Abaevb, Vladimir V. Mel’china, Artem S. Dmitrieva, Arkady S. Pilipenkoa, Alexander S. Shashkovc
a Research Institute of Heterocyclic Compounds Chemistry, Kuban State University of Technology, Moskovskaya st. 2, Krasnodar 350072, Russian Federation
Fax: +7(861)2596592; e-Mail: alexander_butin@mail.ru; e-Mail: av_butin@yahoo.com;
b North-Ossetian State University, Vatutina st. 46, Vladikavkaz 362025, Russian Federation
c N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prospect 47, Moscow 119991, Russian Federation
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Publication History

Received 21 January 2008
Publication Date:
07 April 2008 (online)

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Abstract

As part of our ongoing interest in the synthesis of benz­annelated heterocycles from o-substituted benzylfurans, recyclization of [o-(hydroxymethyl)aryl]difurylmethanes was studied. It was shown that, under acidic conditions, the o-hydroxymethyl group in these compounds acts as a nucleophile and tetracyclic isochromene derivatives are formed via a recyclization-cyclization tandem sequence. Alternatively, these compounds can be synthesized by reduction of the corresponding isochromone derivatives with lithium aluminum hydride. The potent biologically active analogues of cannabinoids were also obtained by interaction of isochromone derivatives with excess of methylmagnesium iodide.

Key words

furans - ring-opening - ring-closure - fused ring system - isochromene