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2005
Thiopyran derivatives
R 0370
Synthesis of Thienothiopyranthiones by a New Molecular Rearrangement. —
title reaction can be carried out in a one-pot fashion by addition of symmetrical
29- 144 The
internal alkynes (II) to dithiole (I) followed by reflux in xylene. The fused thiopyrans
(III) and (IV) are obtained instead of the expected Diels—Alder adducts. Otherwise,
the reaction is carried stepwise via (V), which allows the use of different alkyne substrates. The process is regiospecific. Under more drastic conditions, (I) reacts with
monosubstituted alkynes (VIII). — (OGURTSOV, V. A.; RAKITIN*, O. A.; REES, C.
W.; SMOLENTSEV, A. A.; BELYAKOV, P. A.; GOLOVANOV, D. G.; LYSSENKO,
K. A.; Org. Lett. 7 (2005) 5, 791-794; Zelinsky Inst. Org. Chem., Russ. Acad. Sci.,
Moscow 117913, Russia; Eng.) — Steudel
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