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 α-nitroalkenes or β-nitroacetates provided N-methoxy-N-methyl pyrrole-2-carboxamid...

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Bibliographic Details
Published in:Journal of organic chemistry 2006-08, Vol.71 (17), p.6678-6681
Main Authors: Coffin, Aaron R, Roussell, Michael A, Tserlin, Elina, Pelkey, Erin T
Format: Article
Language:English
Subjects:
Amides - chemistry
Chemistry
Cyanides - chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Molecular Structure
Organic chemistry
Preparations and properties
Pyrroles - chemical synthesis
Pyrroles - chemistry
Pyrrolidines - chemical synthesis
Pyrrolidines - chemistry
Stereoisomerism
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Summary: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 α-nitroalkenes or β-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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo061043m