Tetrahedron

Synthesis of polyfunctionalized furans from 3-acetyl-1-aryl-2-pentene-1, 4-diones

S Onitsuka, H Nishino

Index: Onitsuka, Satoaki; Nishino, Hiroshi Tetrahedron, 2003 , vol. 59, # 6 p. 755 - 765

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Citation Number: 25

Abstract

The BF3-catalyzed cyclization of 3-acetyl-1-aryl-2-pentene-1, 4-diones 1a–e in the presence of water in boiling tetrahydrofuran gave bis (3-acetyl-5-aryl-2-furyl) methanes 2a–e in 26– 79% yields along with a small amount of 3-acetyl-5-aryl-2-methylfurans 3a–e. The exact structure of 2a was determined by X-ray crystallography. The use of a half volume of the solvent for the reaction of 1a resulted in the formation of 2, 4-bis (3-acetyl-5-phenyl-2- ...

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