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Short Paper | Regular issue | Vol 89, No. 4, 2014, pp.1041-1053
Published online, 10th February, 2014
DOI: 10.3987/COM-14-12938
Reinvestigation of 1,3,4-Thiadiazol-2(3H)-iminium Bromide in the Two-Step Synthesis of Imidazo[2,1-b][1,3,4]thiadiazoles

Shigeki Sano,* Keisuke Matsuura, Hayato Sumiyoshi, Akira Miki, Syuji Kitaike, and Michiyasu Nakao

*Molecular Medicinal Chemistry, Graduate School of Pharmaceutical Sciences, The University of Tokushima, 1-78 Sho-machi, Tokushima 770-8505, Japan


The synthesis of 1,3,4-thiadiazol-2(3H)-iminium bromides, which are intermediates in the most commonly used synthetic approach to imidazo[2,1-b][1,3,4]thiadiazoles, and a single crystal X-ray diffraction study of one of these iminium bromides are described. Cyclization of the resulting 1,3,4-thiadiazol-2(3H)-iminium bromides under microwave irradiation afforded imidazo[2,1-b][1,3,4]-thiadiazoles in 80-100% yields.