Online article for Non-subscribers

Pay per view

Heterocycles has a pay-per-view service for Non-subscribers.
You will be able to directly purchase the full text article through PayPal.
Your purchased Paper can be downloaded after the payment is completed.
An e-mail will be sent the URL to download the paper.
If you have any questions, please contact:

Price: ¥ 4,400 (Yen only)
Period: This Article can be accessed for 7 days.

Paper | Special issue | Vol 103, No. 2, 2021, pp.902-917
Published online, 25th February, 2021
DOI: 10.3987/COM-20-S(K)56
Regio-Complementary Preparation of 6- and 7-Fluoro-1,2,3,4-tetrahydroquinolines via the Cyclization of Catecholamines Followed by Deoxyfluorination

Kazuyuki Saito, Wang Zhou, Shohei Sato, Keita Takubo, Kazunori Furutsu, Ahmed A. B. Mohamed, Euis Maras Purwati, Takashi Ikawa, and Shuji Akai*

*Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamada-oka, Suita, Osaka 565–0871, Japan


We herein report a regioselective preparation of 6- and 7-fluoro-1,2,3,4-tetrahydroquinolines by applying the deoxyfluorination strategy, developed by the authors. This method includes the cyclization of catecholamines bearing an N-protecting group to form 7-hydroxy-1-azaspiro[4.5]deca-6,9-dien-8-ones and 6,7-dihydroxy-1,2,3,4-tetrahydroquinolines followed by deoxyfluorination, in which the nature of the N-protecting group has a significant effect on both the cyclization and the regioselectivity of the deoxyfluorination reaction.