Synthesis of functionalized imidazo[4,5- e]thiazolo[3,2- b]triazines by condensation of imidazo[4,5- e]triazinethiones with DMAD or DEAD and rearrangement to imidazo[4,5- e]thiazolo[2,3- c]triazines

Alexei N Izmest'ev; Dmitry B Vinogradov; Natalya G Kolotyrkina; Angelina N Kravchenko; Galina A Gazieva

doi:10.3762/bjoc.17.87

Synthesis of functionalized imidazo[4,5- e]thiazolo[3,2- b]triazines by condensation of imidazo[4,5- e]triazinethiones with DMAD or DEAD and rearrangement to imidazo[4,5- e]thiazolo[2,3- c]triazines

Beilstein J Org Chem. 2021 May 14:17:1141-1148. doi: 10.3762/bjoc.17.87. eCollection 2021.

Authors

Alexei N Izmest'ev^{1

2}, Dmitry B Vinogradov¹, Natalya G Kolotyrkina¹, Angelina N Kravchenko^{1

3}, Galina A Gazieva¹

Affiliations

¹ N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prosp., 47, Moscow 119991, Russian Federation.
² National University of Science and Technology (MISiS), 4 Leninsky prosp., Moscow 119049, Russian Federation.
³ Plekhanov Russian University of Economics, 36 Stremyanny Lane, Moscow 117997, Russian Federation.

Abstract

Two series of functionalized imidazothiazolotriazine derivatives were synthesized via the condensation of imidazo[4,5-e]-1,2,4-triazine-3-thiones with acetylenedicarboxylic acid dimethyl and diethyl esters (DMAD and DEAD) and subsequent base-catalyzed rearrangement of the obtained imidazo[4,5-e]thiazolo[3,2-b]-1,2,4-triazines into regioisomeric imidazo[4,5-e]thiazolo[2,3-c]-1,2,4-triazine derivatives.

Keywords: 1,2,4-triazine; amidine rearrangement; cyclocondensation; heterocycles; thiazolidine-4-one.