Lukin Kirill, Hsu Margaret C, Fernando Dilinie, Leanna M Robert
GPRD Process Research and Development, Abbott Laboratories, North Chicago, Illinois 60064, USA.
J Org Chem. 2006 Oct 13;71(21):8166-72. doi: 10.1021/jo0613784.
The reaction of o-fluorobenzaldehydes and their O-methyloximes with hydrazine has been developed as a new practical synthesis of indazoles. Utilization of the methyloxime derivatives of benzaldehydes (in the form of the major E-isomers) in this condensation effectively eliminated a competitive Wolf-Kishner reduction to fluorotoluenes, which was observed in the direct preparations of indazoles from aldehydes. Reaction of Z-isomers of methyloximes with hydrazine resulted in the formation of 3-aminoindazoles via a benzonitrile intermediate.
邻氟苯甲醛及其邻甲基肟与肼的反应已被开发为一种新的实用的吲唑合成方法。在该缩合反应中使用苯甲醛的甲基肟衍生物（主要为E-异构体形式）有效地消除了竞争性的沃尔夫-基什纳还原反应生成氟甲苯的情况，这种情况在由醛直接制备吲唑时会观察到。甲基肟的Z-异构体与肼反应通过苯甲腈中间体生成3-氨基吲唑。
