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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

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Abstract

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.

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The synthesis of new derivatives of novel selenazolotriazolopyrimidines via Dimroth rearrangement in both acidic and basic media is presented.

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Acknowledgements

The authors gratefully acknowledge the Research Council of Ferdowsi University of Mashhad for financial support of this project (3/44510). JTM thanks Tulane University for support of the Tulane Crystallography Laboratory.

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  1. Department of Chemistryp, Faculty of Science, Ferdowsi University of Mashhad, Mashhad, Iran

    Seddigheh Sheikhi-Mohammareh & Ali Shiri

  2. Department of Chemistry, Tulane University, New Orleans, Louisiana, 70118, USA

    Joel Mague

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Sheikhi-Mohammareh, S., Shiri, A. & Mague, J. 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. Mol Divers 26, 923–937 (2022). https://doi.org/10.1007/s11030-021-10203-9

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