Aminooxygenation of Ynamides with N-Hydroxybenzotriazoles: Synthesis of α-Benzotriazolyl Carbonyl Compounds

Jangbin Im, Sang Ik Shin, Cheon Gyu Cho, Seunghoon Shin

Research output: Contribution to journalArticlepeer-review

6 Scopus citations

Abstract

Addition of N-hydroxybenzotriazoles to ynamides causes spontaneous rearrangement, resulting in α-benzotriazolyl imides. The transformation proceeded at rt in the absence of any catalyst but could be efficiently catalyzed by Zn(OTf)2. Crossover experiments confirmed that the rearrangement is an intramolecular process, most likely via a concerted mechanism. However, heating the mixture above 110 °C resulted in isomerization of N2 into N1 product, via heterolytic C-N bond dissociation. This tandem addition-rearrangement sequence provides an efficient and atom-economical synthetic route for the synthesis of α-benzotriazolyl carbonyl compounds.

Original languageEnglish
Pages (from-to)6935-6950
Number of pages16
JournalJournal of Organic Chemistry
Volume85
Issue number11
DOIs
StatePublished - 2020 Jun 5

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