AI Article Synopsis
- A new and easy method for making 2-amino-1,3,4-oxadiazoles is introduced, which uses tosyl chloride and pyridine to help in the process.
- This method starts with creating a thiosemicarbazide from hydrazide and isothiocyanate, showing better results than using semicarbazides for 18 different cases.
- The protocol efficiently produces various 5-alkyl and 5-aryl 2-amino-1,3,4-oxadiazoles with yields between 78-99%.
Article Abstract
A facile and general protocol for the preparation of 2-amino-1,3,4-oxadiazoles is reported. This method relies on a tosyl chloride/pyridine-mediated cyclization of a thiosemicarbazide, which is readily prepared by acylation of a given hydrazide with the appropriate isothiocyanate. Cyclization of the thiosemicarbazide consistently outperforms the analogous semicarbazide cyclization under these conditions, for 18 distinct examples. Utilizing this protocol, we have prepared 5-alkyl- and 5-aryl-2-amino-1,3,4-oxadiazoles in 78-99% yield.
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| http://dx.doi.org/10.1021/jo0618730 | DOI Listing |
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