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Synthesis of 2 H ‐1,4‐thiazin‐3(4 H )‐one 1‐oxide and 2 H ‐1,4‐thiazin‐3‐(4 H )‐one 1,1‐dioxide, structural analogs of uracil
Author(s) -
Bobek M.
Publication year - 1982
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.5570190125
Subject(s) - chemistry , potassium permanganate , ammonia , thiazine , medicinal chemistry , oxide , organic chemistry
The synthesis of 1,4‐thiazine 1‐oxide and 1,1‐dioxide analogs of the antibiotic emimycin is described. Reaction of methylthioglycolate with 1‐bromo‐2,2‐diethoxyethane gave methyl (2,2‐diethoxyethylthio)acetate ( 2 ). Treatment of 2 with methanolic ammonia followed by cyclization furnished 2 H ‐1,4‐thiazin‐3(4 H )‐one ( 5 ). Oxidation of 5 with m ‐chloroperoxybenzoic acid converted it to 2 H ‐1,4‐thiazin‐3(4 H )‐one 1‐oxide ( 6 ). Oxidation of 2 with potassium permanganate, followed by treatment with methanolic ammonia, and cyclization gave 2 H ‐1,4‐thiazin‐3(4 H )‐one 1,1‐dioxide.