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International Letters of Chemistry, Physics and Astronomy
Volume 30
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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

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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 K2CO3 in acetonitrile.

Info:

Periodical:
International Letters of Chemistry, Physics and Astronomy (Volume 30)
Pages:
265-276
DOI:
10.18052/www.scipress.com/ILCPA.30.265
Citation:
V. C. Kotadiya et al., "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", International Letters of Chemistry, Physics and Astronomy, Vol. 30, pp. 265-276, 2014
Online since:
Mar 2014
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