SELECTIVITY IN DOMINO REACTION OF <i>ORTHO</i>-CARBONYL AZIDES WITH MALONONITRILE DIMER LEADING TO [1,2,3]TRIAZOLO[1,5-<i>a</i>]PYRIMIDINES

Authors

  • Nazariy T. Pokhodylo Department of Organic Chemistry, Ivan Franko National University of Lviv, Kyryla i Mefodiya St. 6, Lviv 79005, Ukraine
  • Olga Ya. Shyyka Ivan Franko National University of Lviv, 6 Kyryla i Mefodiya St., Lviv 79005, Ukraine
  • Mykola A. Tupychak Ivan Franko National University of Lviv, 6 Kyryla i Mefodiya St., Lviv 79005, Ukraine
  • Mykola D. Obushak Ivan Franko National University of Lviv, 6 Kyryla i Mefodiya St., Lviv 79005, Ukraine

DOI:

https://doi.org/10.1007/4256

Keywords:

azides, malononitrile dimer, [1, 2, 3]triazolo[1, 5-a]pyrimidines, domino reaction, selectivity.

Abstract

The selectivity of the domino reaction of the (het)aryl azides, containing the carbonyl center in the ortho position to the azido group, with malonodinitrile dimer was studied. It has been shown that in the case of aromatic azides bearing a carboxy or nitrile function in the ortho position, the reaction occurred with the formation of exclusively [1,2,3]triazolo[1,5-a]pyrimidine instead of [1,2,3]triazolo[4,5-b]pyridine system. Thus, new  [1,2,3]triazolo[1,5-a]quinazolines, thieno[2,3-e][1,2,3]triazolo[1,5-a]pyrimidine, and thieno[3,2-e][1,2,3]triazolo[1,5-a]pyrimidines, having polyfunctional 1-amino-2,2-dicyanovinyl fragment, were prepared in short time in high yields.

Author Biography

Nazariy T. Pokhodylo, Department of Organic Chemistry, Ivan Franko National University of Lviv, Kyryla i Mefodiya St. 6, Lviv 79005, Ukraine

старший научный сотрудник кафедры органической химии

Published

2018-03-23

Issue

Section

Short Communications