title: Phosphine-mediated cascade reaction of azides with MBH-acetates of acetylenic aldehydes to substituted pyrroles: a facile access to N-fused pyrrolo-heterocycles.
abstract: One-pot synthesis of substituted pyrroles by a cascade reaction of azides with Morita-Baylis-Hillman acetates of acetylenic aldehydes is described and the reaction is efficiently mediated by triphenyl phosphine at room temperature. Sodium azide is successfully used to provide N-unsubstituted pyrroles, while alkyl azides afforded the corresponding N-alkylated pyrroles through a sequence of allylic substitution/azide reduction/cycloisomerization reactions. The obtained products have provided a new entry to indolizino indoles, pyrrolo isoquinolines and 8-oxo-5,6,7,8-tetrahydroindolizine.
authors.affiliation: Division of Natural Products Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India. rajireddy@iict.res.in
authors.forename: Chada Raji
authors.initials: CR
authors.lastname: Reddy
authors.forename: Motatipally Damoder
authors.initials: MD
authors.lastname: Reddy
authors.forename: Boinapally
authors.initials: B
authors.lastname: Srikanth
mesh_terms: D000085:Acetates / Q000737:chemistry*; D000447:Aldehydes / Q000737:chemistry*; D000480:Alkynes / Q000737:chemistry*; D001386:Azides / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D007211:Indoles / Q000737:chemistry; D007212:Indolizines / Q000737:chemistry; D007546:Isoquinolines / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010720:Phosphines / Q000737:chemistry*; D011758:Pyrroles / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013696:Temperature
chemical_list: D000085:Acetates; D000447:Aldehydes; D000480:Alkynes; D001386:Azides; D007211:Indoles; D007212:Indolizines; D007546:Isoquinolines; D010720:Phosphines; D011758:Pyrroles