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

被引：10

作者：

Oguma, Takuya ^{[1
]}

Anan, Kosuke ^{[1
]}

Suzuki, Shinji ^{[1
]}

Hisakawa, Shinya ^{[2
]}

Takada, Akihiro ^{[2
]}

Ogawa, Masayoshi ^{[1
]}

Kusakabe, Ken-ichi ^{[1
]}

机构：

[1] Shionogi Pharmaceut Res Ctr, Discovery Res Lab Core Therapeut Areas, 1-1 Futaba Cho 3 Chome, Toyonaka, Osaka 5610825, Japan

[2] Shionogi Pharmaceut Res Ctr, Res Lab Dev, 1-1 Futaba Cho 3 Chome, Toyonaka, Osaka 5610825, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 84卷 / 08期

关键词：

2-OXAZOLINES; CYCLODEHYDRATION; DISEASE;

D O I：

10.1021/acs.joc.8b02179

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 beta-secretase inhibitor 2.

引用

页码：4893 / 4897

页数：5

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