Metal- and Protection-Free [4 + 2] Cycloadditions of Alkynes with Azadienes: Assembly of Functionalized Quinolines

Rakesh K Saunthwal, Monika Patel, Akhilesh K. Verma

Research output: Contribution to journalArticle (Academic Journal)peer-review

Abstract

A base promoted, protection-free, and regioselective synthesis of highly functionalized quinolines via [4 + 2] cycloaddition of azadienes (generated in situ from o-aminobenzyl alcohol) with internal alkynes has been discovered. The reaction tolerates a wide variety of functional groups which has been successfully extended with diynes, (2-aminopyridin-3-yl)methanol, and 1,4-bis(phenylethynyl)benzene to afford (Z)-phenyl-2-styrylquinolines, phenylnaphthyridine, and alkyne-substituted quinolines, respectively. The proposed mechanism and significant role of the solvent were well supported by isolating the azadiene intermediate and deuterium-labeling studies.
Original languageEnglish
Pages (from-to)2200-2203
Number of pages4
JournalOrganic Letters
Volume18
Issue number9
Early online date27 Apr 2016
DOIs
Publication statusPublished - 6 May 2016

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