Facile Synthesis of Tricyclic
Oxazino- or Oxazepino-Fused Tetrahydroquinolines via Intramolecular
Reductive Amidation

Shyamal Mondal; Arindam Maity; Subhendu Naskar; Rupankar Paira; Abhijit Hazra; Krishnendu B. Sahu; Pritam Saha; Saktipada Das; Sukdeb Banerjee; Nirup B. Mondal

doi:10.1055/s-0030-1260056

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Synthesis 2011(13): 2079-2084
DOI: 10.1055/s-0030-1260056

PAPER

Facile Synthesis of Tricyclic Oxazino- or Oxazepino-Fused Tetrahydroquinolines via Intramolecular Reductive Amidation

Shyamal Mondal^a, Arindam Maity^a, Subhendu Naskar^a, Rupankar Paira^a, Abhijit Hazra^a, Krishnendu B. Sahu^a, Pritam Saha^a, Saktipada Das^b, Sukdeb Banerjee^a, Nirup B. Mondal*^a
^a Department of Chemistry, Indian Institute of Chemical Biology, Council of Scientific and Industrial Research, 4 Raja S.C. Mullick Road, Jadavpur, Kolkata 700032, India
Fax: +91(33)24735197; e-Mail: nirup@iicb.res.in;
^b Department of Chemistry, University of Kalyani, Kalyani 741325, India

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Publikationsverlauf

Received 11 January 2011
Publikationsdatum:
19. Mai 2011 (online)

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Abstract

Reductive cyclization of ω-(8-quinolyloxy)alkyl esters by zinc in acetic acid is shown to constitute a convenient methodology for the synthesis of oxazino- or oxazepino-fused tetrahydroquinolines. It is operationally simple, requires a short reaction time, and provides excellent yields.

Key words

reductive amidation - intramolecular amidation - ω-(8-quinolyloxy)alkyl ester - fused tetrahydroquinoline - zinc