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Paper | Regular issue | Vol 36, No. 1, 1993, pp.133-144
Published online, 1st January, 1970
DOI: 10.3987/COM-92-6193
An Efficient and Novel Synthesis of Fused Thiazol-2(3H)-ones

Baldev Singh,* Patrick O. Pennock, George Y. Lesher, Edward R. Bacon, and Donald F. Page

*Department of Medical Chemistry, Sterling Winthrop Pharmaceuticals Research Division, 81 Columbia Turnpike, Rensselaer, NY 12144, U.S.A.


Reaction of o-bromo aromatic amines (2, 4, 7, 10, 15) with ethyl potassium xanthate gave the corresponding fuesd thiazol-2(3H)-thiones (16, 19, 22) which in turn were first alkylated with methyl iodide and then treated with sodium methoxide to produce fused thiazol-2(3H)-ones (18, 21, 24). Treatement of 4-(4-pyridinyl)benzenamine dihydrobromide (1) with DMSO gave 2-bromo-4-(4-pyridinyl)benzenamie (2). Reduction of 4-(4-bromo-3-nitrophenyl)pyridine (3) with stannous chloride gave 2-bromo-5-(4-pyridinyl)benzenamine (4). Treatment of 5-bromo-2-methyl[3,4’-bipyridin]-6(1H)-one (5) with phosphorous oxychloride and ammonia sequentially yielded amino compound (7). Hofmann reaction of 2-chloro-6-methyl[3,4’-bipyridine]-3-carboxamide resulted in amino compound (10). 5-Acyl-6-methylpyridin-2(1H)-ones (11) were converted to 3-bromo-1,6-naphthyridin-2-amines (15) via a four-step sequence.