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Synlett 2006(13): 2035-2038
DOI: 10.1055/s-2006-948179
DOI: 10.1055/s-2006-948179
LETTER
© Georg Thieme Verlag Stuttgart · New York
A Single-Step Synthesis of Symmetrical 1,3-Diarylisobenzofurans
Further Information
Received
31 March 2006
Publication Date:
09 August 2006 (online)
Publication History
Publication Date:
09 August 2006 (online)
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Abstract
A convenient single-step synthesis of various symmetrically substituted 1,3-diarylisobenzofurans from readily available 3-methoxy-3H-isobenzofuran-1-one (1a) and two equivalents of aryl Grignard reagents is described. The title compounds are obtained in medium to high isolated yields. Crude isobenzofuran has also been trapped by maleimide, furnishing pure Diels-Alder adduct almost quantitatively.
Key words
Grignard reactions - Diels-Alder reactions - fused-ring systems - heterocycles - nucleophilic addition
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References and Notes
An alternative pathway could be nucleophilic addition of 3a to the carbonyl group of 1a as the first step. This seems unlikely, as the sole isolated compound resulting from reaction of 1a with only one equiv of 3a was phthalide 4a.