A modular synthesis of unsymmetrical tetraarylazadipyrromethenes.
[reaction: see text] A stepwise route to unsymmetrical tetraarylazadipyrromethenes by a condensation of 2,4-diaryl-5-nitroso-pyrroles with 2,4-diarylpyrroles is described. This modular building-block approach allows for the introduction of up to four different aryl substituents on the azadipyrromethene and is tolerant of a varied substituent set. An efficient synthesis of the 2,4-diarylpyrroles building blocks from 1,3-diaryl-4-nitro-butan-1-ones by nitro hydrolysis to a keto-aldehyde and subsequent ammonia condensation reaction has been achieved. The facile conversion of 2,4-diarylpyrroles into their alpha-nitroso analogues by their reaction with sodium nitrite generated the second building block required for the synthesis.
Hall
Michael J
MJ
Centre for Synthesis and Chemical Biology, Conway Institute, Department of Chemistry, University College Dublin, Belfield, Dublin 4, Ireland.
McDonnell
Shane O
SO
Killoran
John
J
O'Shea
Donal F
DF