1,3-Dipolar Cycloaddition of Nitrile Imines to 2-Imino-thiazolo[3,2-a]pyrimidin-3-ones: Dipole-Initiated Thiazolone-Imidazolone Rearrangement.

IF 3.6 2区化学 Q1 CHEMISTRY, ORGANIC

Journal of Organic Chemistry Pub Date : 2025-10-10 DOI:10.1021/acs.joc.5c00670

Juliana V Petrova,Maria E Filkina,Yuri K Grishin,Vitaly A Roznyatovsky,Victor A Tafeenko,Mikhail S Nechaev,Bogdan I Ugrak,Tatyana Ya Dutova,Artemii M Savin,Arsenii Y Boldyrikhin,Maxim E Kukushkin,Elena K Beloglazkina

引用次数: 0

Abstract

The 1,3-dipolar cycloaddition of nitrile imines to thiazolo[3,2-a]pyrimidine imines featuring both endocyclic and exocyclic C═N bonds was first reported. This reaction resulted in the regio- and stereoselective attachment of two dipole moieties, accompanied by peculiar skeletal rearrangements within the thiazolone fragment. Any products of only dipole addition cannot be isolated. The observed reactivity was explained using DFT protocols to investigate the cyclization mechanism of nitrile imines with thiazolo[3,2-a]pyrimidines.

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腈亚胺与2-亚胺-噻唑[3,2-a]嘧啶-3-酮的1,3-偶极环加成：偶极引发的噻唑-咪唑酮重排。

腈亚胺与具有内环和外环C = N键的噻唑[3,2-a]嘧啶亚胺的1,3-偶极环加成首次被报道。该反应导致两个偶极子部分的区域和立体选择性附着，并伴随着噻唑酮片段内特殊的骨架重排。任何仅偶极子加成的产物都不能被孤立。用DFT协议解释了观察到的反应性，以研究腈亚胺与噻唑[3,2-a]嘧啶的环化机理。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Journal of Organic Chemistry 化学-有机化学

CiteScore

6.20

自引率

11.10%

发文量

1467

审稿时长

2 months

期刊介绍： Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.