Generation of N-H Imines from α-Azidocarboxylic Acids through Ru-Catalyzed Decarboxylation
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SCOPUS
- Title
- Generation of N-H Imines from α-Azidocarboxylic Acids through Ru-Catalyzed Decarboxylation
- Authors
- Jo, Hwi Yul; Lee, Jeong Min; Pietrasiak, Ewa; Lee, Eunsung; Rhee, Young Ho; Park, Jaiwook
- Date Issued
- 2021-12-03
- Publisher
- American Chemical Society
- Abstract
- © 2021 American Chemical Society.A new method for the synthesis of N-H imines from α-azidocarboxylic acids was developed, which proceeds through decarboxylative C-C bond cleavage catalyzed by a commercial diruthenium complex ([CpRu(CO)2]2) under visible light irradiation at room temperature within several minutes. The reactive products undergo condensation, which forms cyclic trimers (2,4,6-trialkylhexahydro-1,3,5-triazines) or linear N,N′-bis(arylmethylidene)arylmethanediamines in quantitative yields. Alternatively, the N-H imines can be trapped with benzylamine and 2-(aminomethyl)aniline, providing stable N-benylimines and tetrahydroquinazolines, respectively. Subsequent oxidation of tetrahydroquinazolines produced quinazolines.
- URI
- https://oasis.postech.ac.kr/handle/2014.oak/109566
- DOI
- 10.1021/acs.joc.1c01841
- ISSN
- 0022-3263
- Article Type
- Article
- Citation
- Journal of Organic Chemistry, vol. 86, no. 23, page. 17409 - 17417, 2021-12-03
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