title: Regiocontrolled synthesis of pyrrole-2-carboxaldehydes and 3-pyrrolin-2-ones from pyrrole Weinreb amides.
abstract: A regiocontrolled synthesis of 3,4-disubstituted pyrrole-2-carboxaldehydes was completed in two steps from acyclic starting materials. A Barton-Zard pyrrole synthesis between N-methoxy-N-methyl-2-isocyanoacetamide and alpha-nitroalkenes or beta-nitroacetates provided N-methoxy-N-methyl pyrrole-2-carboxamides (pyrrole Weinreb amides), which were converted into the corresponding pyrrole-2-carboxaldehydes by treatment with lithium aluminum hydride. A regioselective oxidation of the pyrrole-2-carboxaldehydes gave the corresponding 3,4-disubstituted 3-pyrrolin-2-ones.
authors.affiliation: Department of Chemistry, Hobart and William Smith Colleges, 300 Pulteney St., Geneva, New York 14456, USA.
authors.forename: Aaron R
authors.initials: AR
authors.lastname: Coffin
authors.forename: Michael A
authors.initials: MA
authors.lastname: Roussell
authors.forename: Elina
authors.initials: E
authors.lastname: Tserlin
authors.forename: Erin T
authors.initials: ET
authors.lastname: Pelkey
mesh_terms: D000577:Amides / Q000737:chemistry*; D003486:Cyanides / Q000737:chemistry; D015394:Molecular Structure; D011758:Pyrroles / Q000138:chemical synthesis / Q000737:chemistry*; D011759:Pyrrolidines / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000577:Amides; D003486:Cyanides; D011758:Pyrroles; D011759:Pyrrolidines; C051266:pyrrole-2-carboxaldehyde; C032519:pyrrolidine