144882-55-3Relevant academic research and scientific papers
An efficient approach to pyrroles and N-bridgehead pyrroles by propargylation/cycloamination of 4-amino-1-azabutadiene derivatives
Barluenga, Jose,Tomas, Miguel,Kouznetsov, Vladimir,Suarez-Sobrino, Angel,Rubio, Eduardo
, p. 2185 - 2190 (2007/10/03)
The thermal cycloamination of several propargyl-substituted 4-amino-1-azabutadienes 2 leading to 3-functionalized pyrroles 4-6 is described. Derivatives of pyrrolizidines 9 and indolizidines and azaazulenes 11-13 are synthesized directly from cyclic imines 7 and 10, respectively, in a multistep process that involves metalation with LDA, addition of a nitrile, carbanion trapping with propargyl bromide, and cycloamination. In all cases the more substituted imine nitrogen is involved in the cyclization reaction; such an experimental finding is supported by theoretical calculations.
A Facile Synthesis of N-Bridgehead Pyrroles
Barluenga, Jose,Tomas, Miguel,Kouznetsov, Vladimir,Rubio, Eduardo
, p. 1419 - 1420 (2007/10/02)
A direct entry into the pyrrolizidine, indolizidine and azaazulene systems is accomplished by reaction of metallated cyclic imines with nitriles and prop-2-ynyl bromide.
