One-Pot, Base- and Metal-Free Practical Synthesis of Novel Cycloalkene-Fused [1,4]Thiazepines through the Sequential Ugi/SNCsp2 Reactions

被引：2

作者：

Takallou, Ahmad ^{[1
]}

Al-Shidhani, Sulaiman ^{[1
]}

Anwar, Muhammad U. ^{[1
]}

Al-Harrasi, Ahmed ^{[1
]}

机构：

[1] Univ Nizwa, Nat & Med Sci Res Ctr, POB 33, Birkat Al Mauz 616, Nizwa, Oman

来源：

SYNTHESIS-STUTTGART | 2023年 / 55卷 / 03期

关键词：

thiazepines; sequential reactions; Ugi reaction; fused heterocycles; beta-bromovinyl aldehyde; RING-EXPANSION; UGI; CYCLIZATION; SERIES;

D O I：

10.1055/a-1944-2423

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A one-pot and sequential Ugi/S(N)Csp(2) four-component reaction was introduced for the synthesis of cycloalkene-fused [1,4]thiazepine derivatives. A variety of cyclic.-bromovinyl aldehyde with different sizes, amines, and isocyanides were reacted with thioglycolic acid. This approach can provide a practical and rapid access to the fused bioactive cycloalkene structures containing thiazepine, and peptide unit, which proved the achievement of a significant structural diversity. Further use of this method has been successfully applied in synthesizing a variety of quinoline-fused [1,4]thiazepines with satisfactory results. The practical nature of this approach was demonstrated by a gram-scale synthesis of a selected product.

引用

页码：489 / 498

页数：10

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