1,2 -二氢吡咯[3,2-b]吡咯嵌入七面体的炔环化研究

IF 3.6 2区化学 Q1 CHEMISTRY, ORGANIC

Journal of Organic Chemistry Pub Date : 2024-12-31 DOI:10.1021/acs.joc.4c02538

Gana Sanil, Łukasz Dobrzycki, Michał K. Cyrański, Denis Jacquemin, Wojciech Chaładaj, Daniel T. Gryko

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引用次数: 0

摘要

酸性催化剂性质的剧烈变化使双炔苄环化反应的输出发生逆转。在强Brønsted酸存在下，1,4-二氢吡咯啉发生转化，形成两个7元环。计算研究表明，热力学上不利的7元环是由动力学上有利的吡咯-吡咯3a位置的质子化炔的6-内端攻击和1,2-乙烯移位形成的。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

1,4-Dihydropyrrolo[3,2-b]pyrroles with Two Embedded Heptagons via Alkyne Annulation

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1,4-Dihydropyrrolo[3,2-b]pyrroles with Two Embedded Heptagons via Alkyne Annulation

Drastic changes to the character of the acidic catalyst enable the reversal of the double alkyne benzannulation reaction output. In the presence of a strong Brønsted acid, 1,4-dihydropyrrolopyrroles undergo transformation which results in the formation of two 7-membered rings. Computational studies imply that the thermodynamically unfavored 7-membered ring is forged via the kinetically favored 6-endo-dig attack of a protonated alkyne at the position 3a of pyrrolopyrrole followed by a 1,2-vinyl shift.

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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.