A library of 3-aryl-4,5-dihydroisoxazole-5-carboxamides

Melissa R. Jeddeloh, Jason B. Holden, Dustin H. Nouri, Mark J. Kurth

Research output: Contribution to journalArticle

15 Scopus citations

Abstract

Parallel solution phase methods for the preparation of a 72-membered 3-aryl-4,5-dihydroisoxazole-5-carboxamide library is reported. The reaction order (nitrile oxide 1,3-dipolar cycloaddition followed by amide formation, or vice versa) was investigated both experimentally and computationally to determine which route would result in the highest yields, minimize purification efforts, and give higher 1,3-dipolar cycloaddition regioselectivity. Automated preparative HPLC was used to purify the final products to ≥90% purity on a 10+ mg scale.

Original languageEnglish (US)
Pages (from-to)1041-1045
Number of pages5
JournalJournal of Combinatorial Chemistry
Volume9
Issue number6
DOIs
StatePublished - Nov 2007

ASJC Scopus subject areas

  • Drug Discovery
  • Organic Chemistry
  • Chemistry(all)
  • Discrete Mathematics and Combinatorics

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    Jeddeloh, M. R., Holden, J. B., Nouri, D. H., & Kurth, M. J. (2007). A library of 3-aryl-4,5-dihydroisoxazole-5-carboxamides. Journal of Combinatorial Chemistry, 9(6), 1041-1045. https://doi.org/10.1021/cc700117a