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Synfacts 2010(4): 0400-0400  
DOI: 10.1055/s-0029-1219499
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of 4-Aryl-4-trifluoromethyl-4H-1,3-oxa(thia)zines

Contributor(s): Victor Snieckus, Emilie David
M. V. Vovk*, N. M. Golovach, V. A. Sukach
National Academy of Sciences of Ukraine, Kiev, Ukraine
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Publication History

Publication Date:
22 March 2010 (online)

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Significance

Reported here is the synthesis of S(-)-4-aryl-4-trifluoromethyl-4H-1,3-oxazines 3 and S(-)-4-aryl-4-trifluoromethyl-4H-1,3-thia­zines 4 from S(-)-4-aryl-4-(N-acylamino)-5,5,5-­trifluoropentan-2-ones 2 by reaction with phosphorus pentachloride and pentasulfide, respectively. The proposed mechanism involves the formation of the intermediate imidoyl chloride A and the thioamide B, respectively; the latter undergoing cyclocondensation to C prior to hydrogen sulfide elimination.