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)


Preview

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