title: Tandem Cu-catalyzed ketenimine formation and intramolecular nucleophile capture: Synthesis of 1,2-dihydro-2-iminoquinolines from 1-(o-acetamidophenyl)propargyl alcohols.
abstract: The copper-catalyzed ketenimine formation reaction of 1-(o-acetamidophenyl)propargyl alcohols with various sulfonyl azides is found to undergo a concomitant intramolecular nucleophile attack to generate 1,2-dihydro-2-iminoquinolines after aromatization (via elimination of acetyl and hydroxy groups) and tautomerization. The reaction produces 4-substituted and 3,4-unsubstituted title compounds in moderate to good yields under mild reaction conditions.
authors.affiliation: Medicinal & Process Chemistry Division, CSIR-Central Drug Research Institute, BS-10/1, Sector 10, Jankipuram extension, Sitapur Road, P.O. Box 173, Lucknow 226031, India.|Academy of Scientific and Innovative Research, New Delhi 110001, India.
authors.forename: Gadi Ranjith
authors.initials: GR
authors.lastname: Kumar
authors.affiliation: Academy of Scientific and Innovative Research, New Delhi 110001, India.
authors.forename: Yalla Kiran
authors.initials: YK
authors.lastname: Kumar
authors.affiliation: Molecular & Structural Biology Division, CSIR-Central Drug Research Institute,BS-10/1, Sector 10, Jankipuram extension, Sitapur Road, P.O. Box 173, Lucknow 226031, India.
authors.forename: Ruchir
authors.initials: R
authors.lastname: Kant
authors.affiliation: Medicinal & Process Chemistry Division, CSIR-Central Drug Research Institute, BS-10/1, Sector 10, Jankipuram extension, Sitapur Road, P.O. Box 173, Lucknow 226031, India.|Academy of Scientific and Innovative Research, New Delhi 110001, India.
authors.forename: Maddi Sridhar
authors.initials: MS
authors.lastname: Reddy
keywords: alkyne; azide; cyclization; cycloaddition; quinoline