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Chemistry of the phenoxathiins IV. Synthesis of 9‐substituted 1 ‐azaphenoxathiins
Author(s) -
Martin Gary K.,
Turley James C.
Publication year - 1978
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570150417
Subject(s) - chemistry , nucleus , sulfur , stereochemistry , oxygen atom , organic chemistry , molecule , biology , microbiology and biotechnology
In an extension of recently reported syntheses of the I‐azaphenoxathiin nucleus as well as several 7‐substituted analogs, the synthesis of several 9‐substituted members of this series is now reported. In addition, the first 13 C‐nmr spectral evidence of an interaction between a sulfur atom and the oxygen of an ortho ‐nilro group which has been previously observed only in X‐ray erystallographic studies is also described. The possible consequences of this interaction on the reaction pathway leading to the cyclization of the 9‐substituted J‐azaphenoxathiin nucleus is also presented.