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Synthesis 2011(22): 3716-3722  
DOI: 10.1055/s-0030-1260254
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Regioselective Synthesis of Chromeno[4′,3′:4,5]pyrano[3,2-c][1,8]naph­thyridin-13-one Derivatives by Domino Knoevenagel-Hetero-Diels-Alder Reactions

K. C. Majumdar*a,b, Abu Tahera, Sudipta Ponraa
a Department of Chemistry, University of Kalyani, Kalyani 741235, W.B, India
b Department of Chemical Sciences, Tezpur University, Napaam, Tezpur 784028, Assam, India
Fax: +91(33)25828282; e-Mail: kcm_ku@yahoo.co.in;
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Publication Date:
05 October 2011 (online)

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Abstract

Efficient synthesis of chromeno[4′,3′:4,5]pyrano[3,2-c][1,8]naphthyridin-13-one derivatives has been described by domino Knoevenagel-hetero-Diels-Alder reaction of 4-hydroxy-1-phenyl-1,8-naphthyridin-2(1H)-one with O-allylated/propargylated salicylaldehydes. The reaction occurs in a single step and is highly regio- and stereoselective giving polycyclic heterocycles in high yields.

Key words

1,8-naphthyridine - Knoevenagel reaction - hetero-Diels­-Alder reaction - ethylenediammonium diacetate - regioselective - stereoselective - unactivated alkenes - unactivated alkynes

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