title: A general synthesis of substituted formylpyrroles from ketones and 4-formyloxazole.
abstract: A novel two-step synthesis of substituted 2-formylpyrroles is described. Aldol adducts of ketones and 4-formyloxazole undergo a dehydration/oxazole hydrolysis/cyclization cascade on sequential treatment with MsCl/Et3N and aqueous NaOH to yield 5-substituted and 4,5-disubstituted 2-formylpyrroles. The methodology was extended to an N-benzyl thiazolium salt.
authors.affiliation: Department of Chemical Development, Boehringer Ingelheim Pharmaceuticals Inc, Ridgefield, CT 06877-0368, USA. jreeves@rdg.boehringer-ingelheim.com
authors.forename: Jonathan T
authors.initials: JT
authors.lastname: Reeves
authors.forename: Jinhua J
authors.initials: JJ
authors.lastname: Song
authors.forename: Zhulin
authors.initials: Z
authors.lastname: Tan
authors.forename: Heewon
authors.initials: H
authors.lastname: Lee
authors.forename: Nathan K
authors.initials: NK
authors.lastname: Yee
authors.forename: Chris H
authors.initials: CH
authors.lastname: Senanayake
mesh_terms: D005561:Formates / Q000737:chemistry*; D006900:Hydroxylation; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D010080:Oxazoles / Q000737:chemistry*; D011758:Pyrroles / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: C520454:4-formyloxazole; D005561:Formates; D007659:Ketones; D010080:Oxazoles; D011758:Pyrroles; C030544:formic acid