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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 35, Number 12
BKCSDE 35(12)
December 20, 2014 

Microwave Assisted Synthesis of 1,3,4-Oxadiazole/Thiohydantoin Hybrid Derivatives via Dehydrative Cycliztion of Semicarbazide
Seung-Ju Yang, Jae-Min Lee, Gee-Hyung Lee, NaYeon Kim, Yong-Sang Kim, Young-Dae Gong*
Thiohydantoin, 1,3,4-Oxadiazole, Semicarbazide, Microwave, Amino acid
A series of compounds containing both 1,3,4-oxadiazole and thiohydantoin were synthesized as a promising scaffold for application in medicinal chemistry. The key step of the synthesis is a microwave-assisted cyclization of semicarbazides possessing a thiohydantoin moiety at one of the acyl termini using POCl3 as a dehydrating reagent. A wide range of semicarbazides were prepared through the substitution of hydrazides with an N-acylated thiohydantoin derived from the cyclization of the corresponding isothiocyanate with an amino acid and subsequent N-acylation of the resultant thiohydrantion. Consequently, the 58 number of 1,3,4- oxadiazole derivatives having a thiohydantoin substituent were prepared in good overall yields.
3609 - 3617
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