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

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