One-Pot Synthesis of Pentacyclic Diamines from Quinolines by a New Zn/AcOH-Promoted Cascade Reaction

A simple and efficient method for the one-pot synthesis of pentacyclic diamines from quinolines is described. It involves a new Zn/AcOH-promoted cascade reaction, in which two C−C bonds and four to five stereogenic centers are established under mild conditions. The regiochemistry of the dimerization...

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Bibliographic Details
Published in:Journal of organic chemistry 2002-07, Vol.67 (14), p.4696-4701
Main Authors: Gauffre, Jean-Christophe, Grignon-Dubois, Micheline, Rezzonico, Bernadette, Léger, Jean-Michel
Format: Article
Language:English
Subjects:
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Organic chemistry
Preparations and properties
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Summary:A simple and efficient method for the one-pot synthesis of pentacyclic diamines from quinolines is described. It involves a new Zn/AcOH-promoted cascade reaction, in which two C−C bonds and four to five stereogenic centers are established under mild conditions. The regiochemistry of the dimerization and cyclization step is governed by substituent effects, allowing access to a head-to-head (2, 3) or head-to-tail skeleton (4, 5).
ISSN:0022-3263
1520-6904
DOI:10.1021/jo010961b