Aminooxygenation of Ynamides with N-Hydroxybenzotriazoles: Synthesis of α-Benzotriazolyl Carbonyl Compounds
- Authors
- Im, Jangbin; Shin, Sang Ik; Cho, Cheon Gyu; Shin, Seunghoon
- Issue Date
- Jun-2020
- Publisher
- AMER CHEMICAL SOC
- Citation
- JOURNAL OF ORGANIC CHEMISTRY, v.85, no.11, pp.6935 - 6950
- Indexed
- SCIE
SCOPUS
- Journal Title
- JOURNAL OF ORGANIC CHEMISTRY
- Volume
- 85
- Number
- 11
- Start Page
- 6935
- End Page
- 6950
- URI
- https://scholarworks.bwise.kr/hanyang/handle/2021.sw.hanyang/145561
- DOI
- 10.1021/acs.joc.0c00174
- ISSN
- 0022-3263
- 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.
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