RECYCLIZATION OF CARBONYL-SUBSTITUTED 4<i>Н</i>-CHROMENES AND 1<i>Н</i>-BENZO[<i>f</i>]CHROMENES BY THE ACTION OF AMIDINES AND GUANIDINE: A NOVEL METHOD FOR THE SYNTHESIS OF <i>ortho</i>-HYDROXYBENZYLPYRIMIDINES

Authors

  • Юлия В. Попова Samara State Technical University, 244 Molodogvardeiskaya St., Samara 443100
  • Дарина В. Сахненко Samara State Technical University, 244 Molodogvardeiskaya St., Samara 443100
  • Ирина В. Абузова Samara State Technical University, 244 Molodogvardeiskaya St., Samara 443100
  • Виталий А. Осянин Samara State Technical University, 244 Molodogvardeiskaya St., Samara 443100
  • Дмитрий В. Осипов Samara State Technical University, 244 Molodogvardeiskaya St., Samara 443100
  • Юрий Н. Климочкин Samara State Technical University, 244 Molodogvardeiskaya St., Samara 443100

DOI:

https://doi.org/10.1007/3379

Keywords:

amidines, 1Н-benzo[f]chromenes, 4Н-chromenes, guanidine, pyrimidines, aza-Michael reaction, cascade reactions

Abstract

A series of 2-[(pyrimidin-5-yl)methyl]phenols and 1-[(pyrimidin-5-yl)methyl]-2-naphthols have been accessed via the interaction of carbonyl-substituted 4H-chromenes and 1Н-benzo[f]chromenes with amidines and guanidine in a reaction cascade initiated by the Michael reaction. It was established that in this transformation chromenes act as the synthetic equivalents of hydroxybenzylated αformyl ketones or α-formylaldehydes.

Authors: Yulia V. Popova, Darina V. Sakhnenko, Irina V. Arbuzova, Vitaly A. Osyanin*, Dmitry V. Osipov, Yuri N. Klimochkin

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Published

2016-11-03

Issue

Vol. 52 No. 10 (2016)

Section

Original Papers