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Synthesis 2011(13): 2079-2084  
DOI: 10.1055/s-0030-1260056
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© Georg Thieme Verlag Stuttgart ˙ New York

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

Shyamal Mondala, Arindam Maitya, Subhendu Naskara, Rupankar Pairaa, Abhijit Hazraa, Krishnendu B. Sahua, Pritam Sahaa, Saktipada Dasb, Sukdeb Banerjeea, 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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Publication History

Received 11 January 2011
Publication Date:
19 May 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