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Synthesis 2002(5): 0669-0673
DOI: 10.1055/s-2002-23545
PAPER
© Georg Thieme Verlag Stuttgart · New York

Regioselective Synthesis of Thieno[2,3-b]quinolin-4(9H)-ones: Occurrence of Thermal [1,3] Sigmatropic Rearrangement.

K. C. Majumdar*, M. Ghosh, M. Jana
Department of Chemistry, University of Kalyani, Kalyani -741235, W.Bengal., India
e-Mail: kcm@klyuniv.ernet.in;
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Publication History

Received 3 January 2002
Publication Date:
02 April 2002 (online)

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Abstract

A number of hitherto unreported thieno[2,3-b]quinolin-4(9H)-ones 5a-f have been regioselectively synthesized from the corresponding 4-(prop-2-ynyloxy)quinolin-2(1H)-thiones 4a-f. The 4-(Prop-2-ynyloxy)quinolin-2(1H)-thiones 4a-f were prepared by the thionation of 4-(prop-2-ynyloxy)quinolin-2(1H)-ones 3a-f. The latter compounds were in turn prepared by the alkylation of 4-hydroxyquinolin-2(1H)-one (1).

Key words

Claisen rearrangement - [1,3] sigmatropic rearrangement - sulfur heterocycles - thieno[2,3-b]quinolin-4(9H)-one - [3,3]sigmatropic rearrangement