Microwave‐Assisted Metal‐Free Rapid Synthesis of C4‐Arylated Quinolines via Povarov Type Multicomponent Reaction. Issue 16 (1st April 2019)

• Record Type: Journal Article
• Authors: Chandra, Devesh; Dhiman, Ankit Kumar; Kumar, Rakesh; Sharma, Upendra
• Is Part Of: European journal of organic chemistry. Issue 16(2019)
• Page Start: 2753
• Page End: 2758
• Publication Date: 2019-04-01
• Subjects: Quinolines -- Alkynes -- Povarov reaction -- Microwave synthesis -- Multicomponent reactions; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201900325
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : A rapid microwave assisted, (±) camphor‐10‐sulfonic acid (CSA) promoted, Povarov type multicomponent synthesis of 4‐arylated quinolines from anilines, alkynes, and paraformaldehyde is described. This reaction proceeds through [4+2] cycloaddition of imine (formed in situ from aniline and paraformaldehyde) and alkynes in the presence of CSA, without any metal catalyst. Mechanistic study revealed that CSA inhibit the synthesis of Troger's base and assist the cycloaddition of imines with alkynes by activating the imine. Abstract : Quinoline Synthesis : Three component reaction of aniline, alkynes, and formaldehyde under microwave irradiation promoted by CSA led to the formation of 4‐arylated quinolines via Povarov type reaction.