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An intramolecular Diels–Alder route to novel tetracyclic benzo[b]thiophene derivatives

✍ Scribed by Pilho Kim; Jennifer M. Tsuruda; Marilyn M. Olmstead; Shawn Eisenberg; Mark J. Kurth

Publisher: Elsevier Science
Year: 2002
Tongue: French
Weight: 157 KB
Volume: 43
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(02)00565-8

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✦ Synopsis

A one-pot route to 3-benzo[b]thiophen-2-yl-acrylates (2) from the corresponding thiophenols (1) is reported. Ester reduction and subsequent hydroxyl esterification deliver psuedo trienoates (II) which undergo an intramolecular Diels-Alder (IMDA) reaction to give two 2-oxa-9-thiacyclopenta[b]fluoren-3-one products (I)-the major Diels-Alder product rearomatizes to 7.

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