Vipul C. Kotadiya, Denish J. Viradiya, Bharat H. Baria, Jayendra S. Kanzariya, Rajesh Kakadiya, Anamik Shah, Novel Conversion of 4-Aminoquinolines to New Tricyclic (R,S)-3-Methylazeto[3,2-c] Quinolin-2(2aH)-Ones and Versatile One Step Synthesis of N-(Quinolin-4-yl) Carbamates from 4-Aminoquinolines, Volume 30, International Letters of Chemistry, Physics and Astronomy (Volume 30)
https://www.scipress.com/ILCPA.30.265
Abstract:
    Reaction of 4-aminoquinolines with 4-nitrophenyl chloroformate have resulted in finding a novel transformation of 4-aminoquinolines to tricyclic (R,S)-3-methylazeto[3,2-c]quinolin-2(2aH)-ones. The structure of azeto-quinolinone was determined via spectroscopic and chemical methods. Various alcohols were used as nucleophiles to open the 1-azetinone ring to give the corresponding N-(quinolin-4-yl)carbamates in good yields. We also found a new and versatile one step synthesis of N-(quinolin-4-yl)carbamates by reacting 4-aminoquinolines with alkyl chloroformates in the presence of anhyd K<sub>2</sub>CO<sub>3</sub> in acetonitrile.
Keywords:
    Aminoquinolines, Azeto-Quinolinone, Carbamates, Quinolin