Journal
ORGANIC LETTERS
Volume 22, Issue 2, Pages 515-519Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b04275
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Funding
- National Research Foundation of Korea [NRF-2018R1D1A1B07045397]
- Korea Basic Science Institute (KBSI) National Research Facilities & Equipment Center (NFEC) - Korea government (Ministry of Education) [2019R1A6C1010005]
- MNU Innovative Programs for National University in 2019
- National Research Foundation of Korea [2019R1A6C1010005] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)
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Described herein is the development of a new synthetic route to cyclic amidines from quinolines. The borane-catalyzed 1,4-hydrosilylation of quinoline was utilized for the dearomatization of the quinolines. The dearomatized enamine intermediate was subsequently reacted with a broad range of organic azides to produce the corresponding cyclic amidines (3,4-dihydroquinolinimines) via a [3 + 2] cycloaddition pathway. Preliminary mechanistic studies suggested that the hydride shift was involved during the cycloaddition.
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