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Preparation of indoles from 4 H ‐3,1‐benzothiazines by extrusion of sulfur
Author(s) -
Lednicer Daniel,
Emmert D. Edward
Publication year - 1971
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.5570080604
Subject(s) - chemistry , sulfur , extrusion , benzothiazine , carbon disulfide , base (topology) , aryl , organic chemistry , ring (chemistry) , medicinal chemistry , mathematical analysis , materials science , alkyl , mathematics , metallurgy
Prolonged heating of a series of α ‐hydroxy‐α‐aryl‐ o ‐toluidines in the presence of base and carbon disulfide afforded the corresponding 4 H ‐3,]‐benzothiazine‐2‐thiones. Treatment of the thiolalkyl ethers of these compounds with strong bases led to ring contraction to the corresponding 2‐thioalkyl indole with concommitant extrusion of sulfur. The scope of the reaction was examined.