CYCLOISOMERIZATION – A STRAIGHTFORWARD WAY TO BENZO[<i>h</i>]QUINOLINES AND BENZO[<i>c</i>]ACRIDINES

Authors

  • Mikhail Anatoljevich Kuznetsov Saint Petersburg State University
  • Alena Sergeevna Pankova Saint Petersburg State University
  • Aleksandr Nikolaevich Shestakov Saint Petersburg State University

DOI:

https://doi.org/10.1007/4197

Keywords:

alkynes, benzo[c]acridines, benzo[h]quinolines, pyridines, quinolines, cycloisomerization, synthetic methods

Abstract

Cycloisomerization of 3-alkynyl-2-arylpyridines and quinolines offers a straightforward approach to benzo[h]quinolines and benzo[c]acridines. Substituent at the triple bond governs a choice between transition metal or Brønsted acid catalysis. A direct electrophilic activation by trifluoromethanesulfonic acid induces an almost quantitative cyclization of the ortho-aryl(phenylethynyl) fragment. PtCl2 efficiently catalyzes cyclization of 2-aryl-3-ethynylhetarenes.

Author Biographies

Mikhail Anatoljevich Kuznetsov, Saint Petersburg State University

Head of chair (organic chemistry)

Alena Sergeevna Pankova, Saint Petersburg State University

Dozent, chair of organic chemistry

Aleksandr Nikolaevich Shestakov, Saint Petersburg State University

Doctorand, chair of organic chemistry

Downloads

Published

2017-11-27

Issue

Vol. 53 No. 10 (2017)

Section

Original Papers