Synthesis of a 6-CF3-Substituted 2-Amino-dihydro-1,3-thiazine β-Secretase Inhibitor by N,N-Diethylaminosulfur Trifluoride-Mediated Chemoselective Cyclization

Autor:	Masayoshi Ogawa, Shinji Suzuki, Kosuke Anan, Ken-ichi Kusakabe, Akihiro Takada, Shinya Hisakawa, Takuya Oguma
Rok vydání:	2018
Předmět:	010405 organic chemistry Organic Chemistry 010402 general chemistry 01 natural sciences Medicinal chemistry 0104 chemical sciences Diethylaminosulfur trifluoride chemistry.chemical_compound Trifluoride Thiourea chemistry Thiazine Yield (chemistry) β secretase Chemoselectivity
Zdroj:	The Journal of Organic Chemistry. 84:4893-4897
ISSN:	1520-6904 0022-3263
DOI:	10.1021/acs.joc.8b02179
Popis:	The synthesis of a 6-CF3-substituted 2-amino-dihydro-1,3-thiazine via N,N-diethylaminosulfur trifluoride (DAST)-mediated cyclization of N-hydroxypropyl thiourea 6 is described. This reaction gave 6-CF3-1,3-thiazine 7 with high chemical yield and chemoselectivity, suppressing the common byproduct of oxazine 8. This new protocol enabled access to 6-CF3-substituted 1,3-thiazine β-secretase inhibitor 2.
Databáze:	OpenAIRE
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