Synthesis of 3-Amino-1,5-benzodiazepine-2-one Derivatives from Dehydroalanine Derivatives

被引：3

作者：

Obara, Nobuhiro ^{[1
]}

Watanabe, Takeshi ^{[1
]}

Asakawa, Tomohiro ^{[2
,3
]}

Kan, Toshiyuki ^{[2
]}

Tanaka, Takao ^{[1
]}

机构：

[1] Zeria Pharmaceut Co Ltd, 2512-1 Numagami, Kumagaya, Saitama 3600111, Japan

[2] Univ Shizuoka, Sch Pharmaceut Sci, Suruga Ku, 52-1 Yada, Shizuoka, Shizuoka 4228526, Japan

[3] Tokai Univ, Inst Innovat Sci & Technol, 4-1-1 Kitakaname, Hiratsuka, Kanagawa 2591292, Japan

来源：

SYNTHESIS-STUTTGART | 2019年 / 51卷 / 10期

基金：

日本学术振兴会;

关键词：

1,5-benzodiazepines; Michael additions; o-phenylenediamine; dehydroalanine; intramolecular cyclization; POTENT; ACTIVATION; INHIBITORS;

D O I：

10.1055/s-0037-1611734

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A convenient method was developed for synthesizing 3-amino-1,5-benzodiazepine-2-one derivatives via a Michael addition reaction of o-phenylenediamine with dehydroalanine HFI or HOBt ester derivatives (HFI = 1,1,1,3,3,3-hexafluoro-2-propyl; HOBt = 1,2,3-benzotriazol-1-ol monohydrate), followed by cyclization. Interestingly, the regio- and diastereoselectivities were confirmed by comparing the HFI and HOBt esters. These simple methods were used to synthesize various N-substituted 3-amino-1,5-benzodiazepine-2-one derivatives in good yields.

引用

页码：2198 / 2206

页数：9

共 22 条

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