N-Пропаргилирование и катализируемое медью(I) азид-алкиновое циклоприсоединение как удобная стратегия направленной постсинтетической модификации производных 4-оксо-1,4-дигидроциннолина

Vladimir N. Mikhaylov, Artem O. Pavlov, Ярослав Огороднов, Dar’ya V. Spiridonova, Viktor N. Sorokoumov, Irina A. Balova

Research outputpeer-review

Abstract

[Figure not available: see fulltext.] 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.

Original languageRussian
Pages (from-to)915
Number of pages922
JournalChemistry of Heterocyclic Compounds
Volume56
Issue number7
DOIs
Publication statusPublished - 23 Aug 2020

Scopus subject areas

  • Organic Chemistry

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