<i>N</i>-PROPARGYLATION AND COPPER(I)-CATALYZED AZIDE-ALKYNE CYCLOADDITION AS A CONVENIENT STRATEGY FOR DIRECTED POST-SYNTHETIC MODIFICATION OF 4-OXO-1,4-DIHYDROCINNOLINE DERIVATIVES

Authors

  • Владимир Н. Михайлов Saint Petersburg State University, 7/9 University Embankment, Saint Petersburg 199034
  • Артем О. Павлов Saint Petersburg State University, 7/9 University Embankment, Saint Petersburg 199034
  • Ярослав В. Огороднов Saint Petersburg State University, 7/9 University Embankment, Saint Petersburg 199034
  • Дарья В. Спиридонова Saint Petersburg State University, 7/9 University Embankment, Saint Petersburg 199034
  • Виктор Н. Сорокоумов Saint Petersburg State University, 7/9 University Embankment, Saint Petersburg 199034
  • Ирина А. Балова Saint Petersburg State University, 7/9 University Embankment, Saint Petersburg 199034

DOI:

https://doi.org/10.1007/5778

Keywords:

copper(I) N-heterocyclic carbene complexes, anionic effect, copper(I)-catalyzed azide-alkyne cycloaddition, cross coupling, protein tyrosine phosphatase 1В inhibitors, von Richter cyclization

Abstract

4-Oxo-1,4-dihydrocinnoline derivatives as promising inhibitors of protein tyrosine phosphatase 1В were subjected to post-synthetic modification via a sequence of propargylation and copper(I)-catalyzed azide-alkyne cycloaddition reactions. The propargylation of 4-oxo-1,4-dihydrocinnolines with propargyl bromide in the presence of various bases proceeded regioselectively at the cinnolinone N-1 atom. In the cycloaddition reaction of N-propargylcinnolinones and benzyl azide, the highest catalytic activity of copper(I) N-heterocyclic carbene complex [(IMes)Cu(Br,I)] was observed, compared to [(IMes)CuCl], [(IPr)Cu(Cl,Br,I)], and CuI.

Authors: Vladimir N. Mikhaylov, Artem O. Pavlov, Yaroslav V. Ogorodnov, Dar'ya V. Spiridonova, Viktor N. Sorokoumov, Irina A. Balova*

Author Biography

Владимир Н. Михайлов, Saint Petersburg State University, 7/9 University Embankment, Saint Petersburg 199034

к.х.н., ассистент Института химии СПбГУ

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Published

2020-08-19

Issue

Vol. 56 No. 7 (2020): Synthesis and transformations of heterocycles under electrophilic conditions

Section

Original Papers