title: Mild one-pot Horner-Wadsworth-Emmons olefination and intramolecular N-arylation for the syntheses of indoles, all regio-isomeric azaindoles, and thienopyrroles.
abstract: The syntheses of various N-protected aromatic-ring fused pyrrole-2-carboxylate derivatives have been accomplished using mild one-pot Horner-Wadsworth-Emmons olefination and Cu-catalyzed intramolecular N-arylation reactions. The optimized mild one-pot reaction conditions of various 2-bromo arylcarboxaldehydes with commercially available N-protected phosphonoglycine trimethylesters gave the desired aromatic-ring fused pyrrole-2-carboxylates, such as substituted indole-, all regio-isomeric azaindole-, and thienopyrrole-2-carboxylates, in good to excellent yields. These conditions showed broad substrate compatibility, without the loss of the protecting group.
authors.affiliation: Medicinal Chemistry Research Center, Korea Research Institute of Chemical Technology, Daejeon 305-345, Republic of Korea. indium@krict.re.kr.
authors.forename: Ji Hye
authors.initials: JH
authors.lastname: Choi
authors.forename: Hwan Jung
authors.initials: HJ
authors.lastname: Lim
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D066241:Carbon-13 Magnetic Resonance Spectroscopy; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D066244:Proton Magnetic Resonance Spectroscopy; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D021241:Spectrometry, Mass, Electrospray Ionization
chemical_list: D000475:Alkenes; D007211:Indoles; D011758:Pyrroles