Synthesis of Selenocyanates and Selenoethers of Amino Pyrazoles and Amino Uracils by In Situ Triselenium Dicyanide from Malononitrile and Selenium Dioxide

Danish Ali; Nurabul Mondal; Anoop Kumar Panday; Lokman H Choudhury

doi:10.1021/acsomega.3c02769

Synthesis of Selenocyanates and Selenoethers of Amino Pyrazoles and Amino Uracils by In Situ Triselenium Dicyanide from Malononitrile and Selenium Dioxide

ACS Omega. 2023 Jul 5;8(28):25349-25357. doi: 10.1021/acsomega.3c02769. eCollection 2023 Jul 18.

Authors

Danish Ali¹, Nurabul Mondal¹, Anoop Kumar Panday¹, Lokman H Choudhury¹

Affiliation

¹ Department of Chemistry, Indian Institute of Technology Patna, Bihta, Patna 801106, India.

Abstract

Herein, we report an efficient method for synthesis of novel selenocyanates of amino pyrazole, amino uracil, and amino isoxazole derivatives using in situ triselenium dicyanide from the combination of malononitrile and selenium dioxide in DMSO medium. Using the same combination but changing the stoichiometry of reagents and sequence of addition and temperature, symmetrical selenoethers of amino pyrazoles and amino uracils were prepared in good yields. Furthermore, selenocyanates of amino pyrazoles were utilized for the synthesis of corresponding alkynyl selenides in the presence of CuI and Cs₂CO₃. The salient features of this methodology are inexpensive starting materials, short reaction time, and good to very good yields. This method is also applicable for the gram-scale synthesis of selenocyanates of amino pyrazoles and amino uracils.