Combinatorial synthetic design. Solution and polymer-supported synthesis of heterocycles via intramolecular aza Diels-Alder and imino alcohol cyclizations.

Published

Journal Article

A flexible synthetic strategy for combinatorial chemical applications has been developed on the basis of an aldehyde-bridge-alkene motif as the key component in several intramolecular cycloaddition reactions. This strategy was explored most extensively with the formal aza Diels-Alder cyclization, which affords a series of configurationally and functionally diverse heterocyclic compounds. The substrates included substituted salicylaldehydes, glyoxylic esters and amides, and N-acyl-alpha-aminoaldehydes; all reacted with a variety of anilines to yield different tetrahydroquinoline products. The cyclization of the aminoaldehydes was also translated from solution and optimized for solid phase. The stepwise mechanism of this cycloaddition suggested that the cationic intermediate from initial ring closure could be trapped by a variety of nucleophiles. This suggestion was confirmed by cyclization of amino alcohols and related compounds.

Full Text

Duke Authors

Cited Authors

  • Spaller, MR; Thielemann, WT; Brennan, PE; Bartlett, PA

Published Date

  • September 2002

Published In

Volume / Issue

  • 4 / 5

Start / End Page

  • 516 - 522

PubMed ID

  • 12217025

Pubmed Central ID

  • 12217025

Electronic International Standard Serial Number (EISSN)

  • 1520-4774

International Standard Serial Number (ISSN)

  • 1520-4766

Digital Object Identifier (DOI)

  • 10.1021/cc020027+

Language

  • eng