Regiocontrolled synthesis of pyrrole-2-carboxaldehydes and 3-pyrrolin-2-ones from pyrrole Weinreb amides.
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.
Coffin
Aaron R
AR
Department of Chemistry, Hobart and William Smith Colleges, 300 Pulteney St., Geneva, New York 14456, USA.
Roussell
Michael A
MA
Tserlin
Elina
E
Pelkey
Erin T
ET
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
D000577:Amides; D003486:Cyanides; D011758:Pyrroles; D011759:Pyrrolidines; C051266:pyrrole-2-carboxaldehyde; C032519:pyrrolidine