Synthesis of Some Novel Substituted 4-Aryl-3-Cyano-2-Amino-Thiophene Derivatives

合成新穎之取代基4－芳基－3－氰基－2－胺基－噻吩衍生物

10.6989/JN.201112.0001

何玉文(Yuh-Wen Ho)；邱世龍(Se-Long Chou)

胺基－噻吩 ； 溴化巴豆腈 ； 克諾芬納吉耳縮合反應 ； 取代基胺基－噻吩 ； Aminothiophenes ； bromocrotonitriles ； Knoevenagel condensation ； substituted aminothiophenes

南亞學報

31期（2011 / 12 / 01）

1 - 12

英文

本研究以具取代基之芳基甲基酮化合物1a-f與丙二腈2進行克諾芬納吉耳縮合反應（Knoevenagel condensation）得到含有甲基之巴豆腈衍生物3a-f。將含有甲基之巴豆腈衍生物3a-f在四氯化碳溶劑下與溴進行反應可得溴化巴豆腈衍生物4a-f。最後，將合成之溴化巴豆腈衍生物4a-f與硫氫化納進行環化縮合反應得到目標化合物取代基4－芳基－3－氰基－2－胺基－噻吩新衍生物7a-f。

Knoevenagel condensation of aryl methyl ketones 1a-f with malononitrile 2 gave the corresponding crotonitriles 3a-f. Methyl groups of the crotonitriles 3a-f were then efficiently brominated by refluxing and lightening the reaction media to give bromocrotonitriles 4a-f. On the other hand, the 4-substituted-2-amino-3-cyano-thiophene derivatives 7a-f were obtained by the cyclocondensation reaction bromocrotonitriles 4a-f with NaSH.