Chemoselective protection of heteroaromatic aldehydes as imidazolidine derivatives

Add time:08/04/2019    Source:sciencedirect.com

Furan-, thiophene- and N-methylpyrrole-2-carboxaldehydes may be transformed into the corresponding N,N'-dimethylimidazolidines in a reaction not requiring acid catalysis. The resulting furan and thiophene (but not N-methylpyrrole) derivatives may be metallated in high yields [predominantly at the 5 (α-) positions of the heteroaromatic rings] and the carboxaldehyde functionality regenerated under very mild conditions. Treatment of the aldehydoketone 2-acetyl-5-formylthiophene with N,N'-dimethylethylenediamine gives only the product of reaction at the aldehyde function thus establishing this methodology as a potentially valuable method for the protection of an aldehyde in the presence of a ketone.

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