- Benzotriazole-Mediated Conversions of Aromatic and Heteroaromatic Aldehydes to Functionalized Ketones
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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.
- Katritzky, Alan R.,Lang, Hengyuan,Wang, Zuoquan,Zhang, Zhongxing,Song, Huimin
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p. 7619 - 7624
(2007/10/03)
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- A new simple route to furanic ketones; preparation of elsholtzione naginata ketone and perilla ketone
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Copper- or iron-catalyzed acylation of organomanganese reagents allows to obtain 3- and 2-acylfurans in high yields. Elsholtzione, naginata ketone and perilla ketone have been prepared according to this procedure.
- Cahiez,Chavant,Metais
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p. 5245 - 5248
(2007/10/02)
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- A mild, efficient approach to 3-acylfurans: A short synthesis of perilla ketone
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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.
- Bailey
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p. 242 - 243
(2007/10/02)
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