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, Shuji Akai

Research output: Contribution to journalArticlepeer-review

Abstract

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.

Original languageEnglish
JournalHeterocycles
Volume103
Issue number2
DOIs
Publication statusPublished - 2021

Fingerprint

Dive into the research topics of 'Regio-complementary preparation of 6- And 7-fluoro-1,2,3,4-tetrahydroquinolines via the cyclization of catecholamines followed by deoxyfluorination'. Together they form a unique fingerprint.

Cite this