553-84-4Relevant articles and documents
Benzotriazole-Mediated Conversions of Aromatic and Heteroaromatic Aldehydes to Functionalized Ketones
Katritzky, Alan R.,Lang, Hengyuan,Wang, Zuoquan,Zhang, Zhongxing,Song, Huimin
, p. 7619 - 7624 (2007/10/03)
Aromatic and heteroaromatic aldehydes reacted with benzotriazole and triethyl orthoformate in THF to give the corresponding α-(benzotriazol-1-yl)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.Benzaldehyde, methyl-, chloro-, and methoxy-substituted benzaldehydes, 1-naphthalenecarboxaldehyde, 2- and 3-furaldehydes, 2- and 3-thiophenecarboxaldehydes, and 2-pyridinecarboxaldehyde were all transformed in this manner into a variety of aryl and heteroaryl ketones with alkyl (10), α-hydroxyalkyl (12 and 13), α-aminoalkyl (14) and acyl (15) substituents.
A mild, efficient approach to 3-acylfurans: A short synthesis of perilla ketone
Bailey
, p. 242 - 243 (2007/10/02)
Several 3-acylfurans 3 were prepared in excellent yield using a one-pot procedure involving the palladium-catalyzed cross-coupling of commercially available acid chlorides with tributyl(3-furyl)-stannane 2 at room temperature.