Synthesis
DOI: 10.1055/a-1944-2423
paper

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

Ahmad Takallou
,
Sulaiman Al-Shidhani
,
Muhammad U. Anwar
,
Ahmed Al-Harrasi
We acknowledge financial support from the University of Nizwa.


Abstract

A one-pot and sequential Ugi/SNCsp2 four-component reaction was introduced for the synthesis of cycloalkene-fused [1,4]thiazepine derivatives. A variety of cyclic β-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.

Supporting Information



Publication History

Received: 06 April 2022

Accepted after revision: 14 September 2022

Accepted Manuscript online:
14 September 2022

Article published online:
06 October 2022

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