title: Selective synthesis of substituted pyrrole-2-phosphine oxides and -phosphonates from 2H-azirines and enolates from acetyl acetates and malonates.
abstract: A simple and efficient selective synthesis of 1H-pyrrole-2-phosphine oxides 3 and -phosphonates 7 by addition of enolates derived from acetyl acetates to 2H-azirinylphosphine oxide 1 and -phosphonate 6 is reported. Nucleophilic addition of enolates derived from diethyl malonate to 2H-azirines 1 and 6 led to the formation of functionalized 2-hydroxy-1H-pyrrole-5-phosphine oxide 9 and -phosphonate 10, while vinylogous α-aminoalkylphosphine oxides 14 and -phosphonate 15 may be obtained from azirines and the enolate derived from diethyl 2-phenylmalonate. Ring closure of vinylogous derivatives 14 and 15 in the presence of base led to the formation of 1,5-dihydro-3-pyrrolin-2-ones containing a phosphine oxide 17 or a phosphonate group 18.
authors: Departamento de Química Orgánica I, Facultad de Farmacia, Centro de Investigaciones y Estudios Avanzados Lucio Lascaray, Universidad del País Vasco, 01080 Vitoria, Spain. francisco.palacios@ehu.es
authors: Francisco
authors: F
authors: Palacios
authors: Ana M
authors: AM
authors: Ochoa de Retana
authors: Ander
authors: A
authors: Vélez del Burgo
mesh_terms: D000085:Acetates / Q000737:chemistry*; D001389:Azirines / Q000138:chemical synthesis* / Q000737:chemistry; D002264:Carboxylic Acids / Q000737:chemistry*; D008314:Malonates / Q000737:chemistry*; D015394:Molecular Structure; D063065:Organophosphonates / Q000138:chemical synthesis* / Q000737:chemistry; D009943:Organophosphorus Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D010720:Phosphines / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000085:Acetates; D001389:Azirines; D002264:Carboxylic Acids; D008314:Malonates; D063065:Organophosphonates; D009943:Organophosphorus Compounds; D010720:Phosphines; C044646:phosphine