Base mediated sequentialnitrogen insertion and benzotriazolationof p-quinone methides

TitleBase mediated sequentialnitrogen insertion and benzotriazolationof p-quinone methides
Publication TypeJournal Article
Year of Publication2026
AuthorsMamale, AG, Ghodake, BM, Bhattacharya, AK
JournalJournal of Organic Chemistry
Volume91
Issue30
Pagination10414-10424
Date PublishedJUL
Type of ArticleArticle
ISSN0022-3263
Abstract

Herein, we report a base-mediated, one-pot protocol for the synthesis of functionalized benzotriazole derivatives via in situ generation of benzotriazoles from benzene-1,2-diamines and tert-butyl nitrite. The transformation proceeds through nitrogen insertion, followed by a subsequent 1,6-aza-Michael addition with p-quinone methides, enabling efficient C-N bond formation. Notably, the developed method operates under mild, transition-metal-free conditions and is performed under an open-air atmosphere, offering a practical and environmentally benign approach to structurally diverse benzotriazoles and demonstrated 34 examples of <= 87% yield with wide functional group tolerance.

DOI10.1021/acs.joc.6c00862
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)

3.3

Divison category: 
Organic Chemistry
Database: 
Web of Science (WoS)

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