Abstract: Reactions of perfluoro(3-isothiocyanato-2-methyl-2-pentene) with N-nucleophiles (morpholine, dibutylamine, and piperidine) in acetonitrile yield products of addition to the carbon atom of the isothiocyanato group, 1,1-disubstituted 3-(3,3,3-trifluoro-1-pentafluoroethyl-2-trifluoromethylpropylidene)thioureas. The reaction with diethylamine yields 2-diethylamino-4-pentafluoroethyl-5-trifluorornethyl-6H-1,3-thiazin-6-one. The thiourea derivatives undergo intramolecular cyclization into 2-dialkylamino-6H-1,3-thiazines when treated with a base (potassium carbonate or triethylamine) in DMF. 6,6-Difluoro-4-pentafluoroethyl-2-piperidino-5-trifluoromethyl-6H-1,3-thiazine is hydrolyzed with atmospheric moisture to afford 4-pentafluoroethyl-2-piperidino-5-trifluoromethyl-6H-1,3-thiazin-6-one. Possible reaction pathways and factors influencing the intramolecular nucleophilic cyclization are discussed.

Cite: Furin G.G. , Pressman L.S. , Rogoza A.V. , Salmanov I.A.
Synthesis of 6H-1,3-Thiazine Derivatives from Perfluoro(3-isothiocyanato-2-methyl-2-pentene)
Russian Journal of Organic Chemistry. 1997. V.33. N5. P.720-724. Scopus РИНЦ

Original: Furin G.G. , Pressman L.S. , Rogoza A.V. , Salmanov I.A.
Preparation of 6H-[1,3]thiazine derivatives using perfluoro(2-methyl-2-pentene-3-isothiocyanate)
Журнал органической химии (RUSS J ORG CHEM+). 1997. V.33. N5. P.782-786. WOS

Identifiers:

Scopus:	2-s2.0-0031313125
Elibrary:	13274981

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