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2 H ‐1,4‐benzothiazines from the reaction of 2‐aminoethanethiol with nascent 4‐methyl‐ o ‐benzoquinone
Author(s) -
Prota G.,
Petrillo O.,
Santacroce C.,
Sica D.
Publication year - 1970
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.5570070313
Subject(s) - chemistry , benzothiazine , benzoquinone , medicinal chemistry , organic chemistry
4‐Methyl‐ o ‐benzoquinone, generated oxidatively, reacts readily with 2‐aminoethanethiol giving 5‐hydroxy‐7‐methyl‐1,3,4‐dihydro‐2 H ‐1,4‐benzothiazine (I) or 5‐oxo‐7‐methyl‐8‐(2‐hydroxy‐4‐methylphenoxy)‐3,5‐dihydro‐2 H ‐1,4‐benzothiazine (VIII), depending on the conditions under which the reaction is performed. Chemical and spectral (uv, ir, nmr and ms) evidence for the assigned structures, as well as the course of the above mentioned reaction is described. A study of the behaviour of compound VIII in the presence of acids and alkalies is also reported.