Synthesis 2015; 47(18): 2745-2755
DOI: 10.1055/s-0034-1380431
special topic
© Georg Thieme Verlag Stuttgart · New York

Exploration of C5–C6-Unsubstituted 1,4-Dihydropyridines for the Construction of exo-Hexahydro-1H-chromeno[3,4-h][1,6]naphthyridine-3-carboxylates Using a Stereoselective Povarov Reaction

Kobirul Islam
a  Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati 781039, India
,
Deb K. Das
a  Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati 781039, India
,
Ejaz Akram
a  Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati 781039, India
,
Abu T. Khan*
a  Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati 781039, India
b  Aliah University, IIA/27, New Town, Kolkata 700 156, West Bengal, India   Email: atk@iitg.ernet.in
› Author Affiliations
Further Information

Publication History

Received: 04 April 2015

Accepted after revision 12 May 2015

Publication Date:
02 July 2015 (online)

This work is dedicated to my mentor, retired Professor Dr. R. R. Schmidt, Department of Chemistry, University of Konstanz, Germany, on the occasion of his 80th birthday.�

Abstract

A wide variety of substituted exo-hexahydro-1H-chromeno[3,4-h][1,6]naphthyridine-3-carboxylate derivatives have been synthesized from 3-aminocoumarins, aldehydes, and 5,6-unsubstituted 1,4-dihydropyridine derivatives in the presence of 10 mol% of ytterbium(III) triflate in acetonitrile at room temperature using a one-pot Povarov reaction. Some of the salient features of this protocol are: good yields and no need for an aqueous workup procedure or chromatographic separation.

Supporting Information

 
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