A Modular Synthesis of Unsymmetrical Tetraarylazadipyrromethenes
- 15 June 2005
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 70 (14), 5571-5578
- https://doi.org/10.1021/jo050696k
Abstract
[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.This publication has 22 references indexed in Scilit:
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