Intramolecular cyclization of β,β-difluorostyrenes bearing an iminomethyl or a diazenyl group at the ortho position: synthesis of 3-fluorinated isoquinoline and cinnoline derivatives,10.1039/B712965C

热搜：

Lactoyl-CoA 全氟丁基戊烷白叶藤碱全氟己基辛烷新白叶藤碱壳寡糖特色专题-生物多肽

Intramolecular cyclization of β,β-difluorostyrenes bearing an iminomethyl or a diazenyl group at the ortho position: synthesis of 3-fluorinated isoquinoline and cinnoline derivatives

Junji Ichikawa,Yukinori Wada,Hiroyuki Kuroki,Jun Mihara,Ryo Nadano

Organic & Biomolecular Chemistry Pub Date : 10/23/2007 00:00:00 , DOI:10.1039/B712965C

Abstract

o-Formyl-substituted β,β-difluorostyrenes readily react with NH₂OH·HCl or NH₄OAc to afford 3-fluoroisoquinoline derivatives in good yield via (i) the formation of the corresponding oximes or imines and (ii) subsequent intramolecular replacement of a vinylic fluorine by the sp² nitrogen of the iminomethyl group (HON [double bond, length as m-dash] CH– or HNCH–). β,β-Difluorostyrenes bearing an o-diazenyl group (HNN–), generated by reduction of the corresponding diazonium ions, undergo a similar substitution to afford 3-fluorinated cinnolines.