Dimroth rearrangement-based synthesis of novel derivatives of [1,3]selenazolo[5,4-e][1,2,4]triazolo[1,5-c]pyrimidine as a new class of selenium-containing heterocyclic architecture

As a part of our ongoing endeavor towards developing novel heterocyclic architectures, a number of novel Se-containing tricyclic heterocycles of the type [1,3]selenazolo[5,4-e][1,2,4]triazolo[1,5-c]pyrimidine have been synthesized through heteroannulation of a newly produced hydrazino derivative of selenazolo[4,5-d]pyrimidine with either orthoesters or carbon disulfide in pyridine followed by S-alkylation. Moreover, the multistep protocol employed in this investigation provides a new insight into the Dimroth rearrangement in both acidic and basic media as a means for the cyclocondensation of triazole on the selenazolopyrimidine framework leading to selenazolotriazolopyrimidines. [GRAPHICS] .

Automated summary

A series of novel Se-containing tricyclic heterocycles have been synthesized through heteroannulation of a newly produced hydrazino derivative of selenazolo[4,5-d]pyrimidine with either orthoesters or carbon disulfide in pyridine followed by S-alkylation, providing new insight into the Dimroth rearrangement in both acidic and basic media for cyclocondensation of triazole on the selenazolopyrimidine framework leading to selenazolotriazolopyrimidines.