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

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

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