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1,2,6-噻二嗪1-氧化物:源自磺酰亚胺酰胺的不饱和三维S,N-杂环化合物。

1,2,6-Thiadiazine 1-Oxides: Unsaturated Three-Dimensional S,N-Heterocycles from Sulfonimidamides.

作者信息

Schöbel Jan-Hendrik, Passia Marco Thomas, Wolter Nadja Anna, Puttreddy Rakesh, Rissanen Kari, Bolm Carsten

机构信息

Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, D-52074 Aachen, Germany.

University of Jyvaskyla, Department of Chemistry, P.O. Box 35, FI-40014 Jyväskylä, Finland.

出版信息

Org Lett. 2020 Apr 3;22(7):2702-2706. doi: 10.1021/acs.orglett.0c00666. Epub 2020 Mar 16.

Abstract

Unprecedented three-dimensional 1,2,6-thiadiazine 1-oxides have been prepared by an aza-Michael-addition/cyclization/condensation reaction sequence starting from sulfonimidamides and propargyl ketones. The products have been further functionalized by standard cross-coupling reactions, selective bromination of the heterocyclic ring, and conversion into a β-hydroxy substituted derivative. A representative product was characterized by single-crystal X-ray structure analysis.

摘要

通过从磺酰亚胺酰胺和炔丙基酮开始的氮杂迈克尔加成/环化/缩合反应序列,制备了前所未有的三维1,2,6-噻二嗪1-氧化物。产物通过标准交叉偶联反应、杂环的选择性溴化以及转化为β-羟基取代衍生物进一步官能化。通过单晶X射线结构分析对代表性产物进行了表征。

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