新型方便的方法构建含内酰胺磺酰胺片段的 6-、7- 和 8-元氮杂环

Novel Convenient Approach to 6-, 7-, and 8-Numbered Nitrogen Heterocycles Incorporating Endocyclic Sulfonamide Fragment.

机构信息

Department of Heteroatom Chemistry, Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Murmans'ka, 02660 Kyiv, Ukraine.

Department of Mechanisms of Bioorganic Reactions, V.P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry, National Academy of Sciences of Ukraine, 1 Murmans'ka, 02094 Kyiv, Ukraine.

出版信息

Molecules. 2020 Jun 23;25(12):2887. doi: 10.3390/molecules25122887.

DOI:10.3390/molecules25122887

PMID:32585918

原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7356088/

Abstract

A new effective method for the construction of nitrogen heterocycles incorporating endocyclic pharmacophore sulfonamide fragment, based on the use of easy accessible -(chlorosulfonyl)imidoyl chloride, CClC(Cl)=NSOCl (), has been developed. Thus, a reaction of as bielectrophilic 1,3-C-N-S reagent with benzylamines that act as 1,4-N-C-C-C binucleophiles, affords respective 1,2,4-benzothiadiazepine-1,1-dioxides. On the other hand, reacts with alkenyl amines with the formation of respective -alkenyl amidines undergoing Lewis acids initiated intramolecular cyclization to afford derivatives of 1,2,4-thiadiazines and 1,2,4-thiadiazocines bearing a halomethyl group able for further functionalization. The first examples of electrophilic heterocyclization of the chlorosulfonyl group onto an alkenyl or alkynyl group have been revealed.

摘要

一种新的有效方法，用于构建含有中环药效团磺酰胺片段的氮杂环，基于使用易得的-（氯磺酰基）异氰酰氯，CClC（Cl）=NSOCl（），已经被开发出来。因此，作为双亲试剂的与作为 1,4-N-C-C-C 双亲核试剂的苄胺的反应，得到相应的 1,2,4-苯并噻二嗪-1,1-二氧化物。另一方面，与烯基胺反应，形成各自的-烯基脒，经历路易斯酸引发的分子内环化，得到含有卤甲基基团的 1,2,4-噻二嗪和 1,2,4-噻二嗪酮衍生物，能够进一步官能化。首次揭示了氯磺酰基在烯基或炔基上的亲电杂环化反应。