58803-92-2Relevant articles and documents
Mechanism of the Formation of N,N-Dialkyl-2-pyrrolecarboxamides from 1,3-Diketones and N,N-Dialkyloximinoacetatoacetamides
Paine, John B.,Brough, Jonathan R.,Buller, Kathy K.,Erikson, Erika E.
, p. 3993 - 3997 (2007/10/02)
The mechanism of formation of N,N-dialkyl-2-pyrrolecarboxamides 1 from the reaction between N,N-dialkyl-2-(hydroxyimino)-3-oxoalkanamides 4 and meso-substituted β-diketones 2 upon treatment with zinc in acetic acid differs from the analogous reaction between 2-(hydroxyimino)-3-oxoalkanoate esters and 2.The 3-substituent of 1 is found to be derived exclusively from 4, not 2.Parallel behavior was observed in the regioselectivity of reaction of 2-acylcycloalkanones 19 with 4 or with diethyl aminomalonate (14b).The strong preference of 2-acylcyclopentanones 19c,d for initial reaction at the exocyclic carbonyl led to the formation of pyrrole-3-butanoic acids 22c,d by ring-opening, in good yield. 2-Acylcyclohexanones 19a,b, by contrast, gave good yields of a tetrahydroindole (26).
