Issue 24, 2007
From the journal:

Organic & Biomolecular Chemistry

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,*a   Yukinori Wada,b   Hiroyuki Kuroki,c   Jun Miharab  and  Ryo Nadanob  

* Corresponding authors

a Department of Chemistry, Graduate School of Pure and Applied Sciences, University of Tsukuba, Tsukuba, Ibaraki 305-8571, Japan
E-mail: junji@chem.tsukuba.ac.jp
Fax: +81 29 853 4237
Tel: +81 29 853 4237

b Department of Chemistry, Graduate School of Science, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan

c Department of Applied Chemistry, Kyushu Institute of Technology, Sensui-cho, Tobata, Kitakyushu 804-8550, Japan

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 HN[double bond, length as m-dash]CH–). β,β-Difluorostyrenes bearing an o-diazenyl group (HN[double bond, length as m-dash]N–), generated by reduction of the corresponding diazonium ions, undergo a similar substitution to afford 3-fluorinated cinnolines.

Graphical abstract: 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

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Article information

DOI
https://doi.org/10.1039/B712965C
Article type
Paper
Submitted
22 Aug 2007
Accepted
02 Oct 2007
First published
23 Oct 2007

Org. Biomol. Chem., 2007,5, 3956-3962

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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

J. Ichikawa, Y. Wada, H. Kuroki, J. Mihara and R. Nadano, Org. Biomol. Chem., 2007, 5, 3956 DOI: 10.1039/B712965C

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