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3‐Thiolcoumarin and its derivatives
Author(s) -
ChiYi Hsing,
WenJiang Wang,
DaYan He
Publication year - 1987
Publication title -
acta chimica sinica english edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 0256-7660
DOI - 10.1002/cjoc.19870050209
Subject(s) - thioether , chemistry , coumarin , intramolecular force , ring (chemistry) , michael reaction , intermolecular force , medicinal chemistry , stereochemistry , tricyclic , organic chemistry , molecule , catalysis
3‐Thiolcoumarin (8) and 3,3′‐dithio‐biscoumarin (9) were prepared. When compound (8) reacted with various Michael acceptors, some of the intermolecular primary addition products were followed by a sequential intramolecular Michael addition with ring closure forming a series of tetrahydro‐thieno [2,3‐c][1]benzopyran‐4(H)‐one derivatives ( e.g. 16), the formation of which depends upon the structures of the acceptors. The stereochemistry of the tricyclic compounds was determined and discussed. The allyl thioethers of compound (8) were prepared. 3‐Allyl coumarin thioether (26) was subjected to Claisen rearrangement in N, N ‐dimethylaniline, the expected rearranged products (27) and (28) being obtained. However, 3‐cinnamyl coumarin thioether (29) under the same condition gave 3‐( p‐N,N ‐dimethylamino) thiobenzyl‐coumarin (32) and other products. Phenyl cinnamyl thioether reacted similarly giving p‐(N,N ‐dimethylamino)benzyl phenyl thioether (35).