Regioselective synthesis of pyrroloquinolines — Approaches to Martinelline

Indium trichloride catalysed Diels-Alder reaction of imines derived from anilines with cyclic enamides regioselectively gave the biologically important pyrroloquinoline nucleus, with a cis ring junction, in moderate yield. Although the exo:endo selectivity was in most cases poor, these isomers are r...

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Bibliographic Details
Published inTetrahedron letters Vol. 40; no. 6; pp. 1215 - 1218
Main Authors Hadden, Mark, Stevenson, Paul J.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 05.02.1999
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
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Summary:Indium trichloride catalysed Diels-Alder reaction of imines derived from anilines with cyclic enamides regioselectively gave the biologically important pyrroloquinoline nucleus, with a cis ring junction, in moderate yield. Although the exo:endo selectivity was in most cases poor, these isomers are readily separated by flash chromatography. The functionality tolerated at both C2 and C7 should allow further elaboration to Martinelline Imino Diels-Alder reaction of imines derived from aromatic amines with cyclic enamides regioselectively gave pyrroloquinolines with a cis-ring junction.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(98)02569-6