MICROWAVE-ASSISTED SEQUENTIAL THREE-COMPONENT SYNTHESIS OF PYRROLYL-SUBSTITUTED CHROMENO[2,3-<i>c</i>]ISOQUINOLIN-5-AMINES

Authors

  • Xiaoyi Yue Peoples’ Friendship University of Russia
  • Olga A. Storozhenko Peoples’ Friendship University of Russia
  • Alexey A. Festa Peoples’ Friendship University of Russia
  • Elena A. Sorokina Peoples’ Friendship University of Russia
  • Alexey A. Varlamov Peoples’ Friendship University of Russia
  • Leonid G. Voskressensky Peoples’ Friendship University of Russia

DOI:

https://doi.org/10.1007/5483

Keywords:

2-aminochromene, isoquinolin-5-amines, salicylaldehyde, domino reaction, multicomponent reaction.

Abstract

Sequential one-pot domino reaction of homophthalonitrile, salicylaldehydes, and pyrroles in basic media under MW irradiation results in the formation of novel chromeno[2,3-c]isoquinolin-5-amines. The transformation represents a domino sequence that starts with Knoevenagel condensation, followed by two nucleophilic cyclizations, consecutively forming 2-iminochromene and 5-iminoisoquinoline cycles. Michael addition of the pyrrole unit to the chromene cycle finishes the transformation. The reaction tolerates various salicylaldehydes and pyrroles, producing target molecules with good 45–67% yields.

Published

2020-04-30