Iodocyclization of Hydroxylamine Derivatives Based on the Control of Oxidative Aromatization Leading to 2,5-Dihydroisoxazoles and Isoxazoles
- 30 March 2011
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 76 (9), 3438-3449
- https://doi.org/10.1021/jo200407b
Abstract
An efficient method for the synthesis of 2,5-dihydroisoxazoles and isoxazoles using iodocyclization of N-alkoxycarbonyl O-propargylic hydroxylamines has been developed. 2,5-Dihydro-4-iodoisoxazole underwent the cross-coupling reactions without aromatization to afford polyfunctionalized 2,5-dihydroisoxazoles. This process was applied to the preparation of valdecoxib and its 2,5-dihydro-derivative.Keywords
This publication has 58 references indexed in Scilit:
- Iodine/Palladium Approaches to the Synthesis of Polyheterocyclic CompoundsThe Journal of Organic Chemistry, 2010
- Molecular Iodine-Mediated Cyclization of Tethered Heteroatom-Containing Alkenyl or Alkynyl SystemsMolecules, 2009
- Competition Studies in Alkyne Electrophilic Cyclization ReactionsThe Journal of Organic Chemistry, 2008
- Synthesis of 4,5‐Dihydroisoxazoles by Condensation of Primary Nitro Compounds with Alkenes by Using a Copper/Base Catalytic SystemChemistry – A European Journal, 2008
- The Synthesis of Highly Substituted Isoxazoles by Electrophilic Cyclization: An Efficient Synthesis of ValdecoxibThe Journal of Organic Chemistry, 2007
- Synthesis of 3,4-Disubstituted 2H-Benzopyrans through C−C Bond Formation via Electrophilic CyclizationThe Journal of Organic Chemistry, 2007
- 1-Naphthylpropargyl Ether Group: A Readily Cleaved and Sterically Minimal Protecting System for Stereoselective GlycosylationOrganic Letters, 2006
- Suppression of azoxymethane‐induced colon cancer development in rats by a cyclooxygenase‐1 selective inhibitor, mofezolacCancer Science, 2006
- Direct Intramolecular Arylation of Aldehydes Promoted by Reaction with IPy2BF4/HBF4: Synthesis of Benzocyclic KetonesAngewandte Chemie, 2006
- Synthesis of Spiro[4.5]trienones by Intramolecular ipso-Halocyclization of 4-(p-Methoxyaryl)-1-alkynesJournal of the American Chemical Society, 2005