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J Org Chem ; 71(17): 6678-81, 2006 Aug 18.
Article in English | MEDLINE | ID: mdl-16901171

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.


Subject(s)
Amides/chemistry , Pyrroles/chemistry , Pyrrolidines/chemistry , Cyanides/chemistry , Molecular Structure , Pyrroles/chemical synthesis , Pyrrolidines/chemical synthesis , Stereoisomerism
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