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Intramolecular Hetero‐ Diels–Alder Reactions Catalyzed by BiCl 3 : Stereoselective Synthesis of Benzo‐Annelated Decahydrofuro[3,2‐ h ][1,6]naphthyridine Derivatives
Author(s) -
Sabitha Gowravaram,
Maruthi Chittapragada,
Reddy Erigala Venkata,
Srinivas Chitti,
Yadav Jhillu S.,
Dutta Samit K.,
Kunwar Ajit C.
Publication year - 2006
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200690243
Subject(s) - chemistry , intramolecular force , stereoselectivity , catalysis , aldehyde , medicinal chemistry , chloride , organic chemistry , stereochemistry
A novel, efficient synthesis of a series of functionalized, benzo‐annelated decahydrofuro[3,2‐ h ][1,6]naphthyridine derivatives 3 has been achieved. The protocol is based on the intramolecular hetero‐ Diels–Alder (IMHDA) reaction of in situ formed imines derived from an N ‐prenylated sugar aldehyde 1 and different aromatic amines 2 in the presence of bismuth(III) chloride as catalyst. The reactions could be run under very mild conditions at room temperature, and were complete within 30 min, affording exclusively and stereoselectively the corresponding trans ‐fused products 3 in good‐to‐excellent yields ( Table ).