Trifluoroacetic acid: a more effective and efficient reagent for the synthesis of 3-arylmethylene-3,4-dihydro-1H-quinolin-2-ones and 3-arylmethyl-2-amino-quinolines from Baylis–Hillman derivatives via Claisen rearrangement

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• 作者：Richa Pathak ; Sudharshan Madapa ; Sanjay Batra
• 关键词：Baylis– ; Hillman ; TFA ; Claisen rearrangement ; 3-Arylmethyl-3 ; 4-dihydro-1H-quinolin-2-one ; 3-Arylmethyl-2-amino-quinoline
• 刊名：Tetrahedron
• 出版年：2007
• 出版时间：8 January 2007
• 年：2007
• 卷：63
• 期：2
• 页码：451-460
• 全文大小：324 K

文摘

Trifluoroacetic acid has been discovered to be a highly effective and efficient reagent for the tandem Claisen rearrangement and cyclization reaction to yield 3-arylmethylene-3,4-dihydro-1H-quinolin-2-ones from compounds obtained from the S_N2 reaction between anilines and acetyl derivatives of Baylis–Hillman adducts of acrylates in the presence of DABCO. In contrast, similar compounds obtained from the acetyl derivatives of Baylis–Hillman adduct of acrylonitrile on treatment with trifluoroacetic acid directly furnish 3-arylmethyl-2-amino-quinoline via tandem Claisen rearrangement, cyclization and isomerization.