Benzotriazole-mediated conversions of aromatic and heteroaromatic aldehydes to functionalized ketones

AR Katritzky, H Lang, Z Wang, Z Zhang…

Index: Katritzky, Alan R.; Lang, Hengyuan; Wang, Zuoquan; Zhang, Zhongxing; Song, Huimin Journal of Organic Chemistry, 1995 , vol. 60, # 23 p. 7619 - 7624

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Citation Number: 56

Abstract

Aromatic and heteroaromatic aldehydes reacted with benzotriazole and triethyl orthoformate in THF to give the corresponding a-(benzotriazol-1-y1) aryl ethyl ethers 7 in good yield. The novel acyl anion precursors 7 underwent smooth lithiation at the methine group followed by trapping with alkyl halides, aldehydes, ketones, and imines to yield the expected substituted intermediates of type 9, which were hydrolyzed under mild conditions without isolation. ...