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Superior Reactivity of Thiosemicarbazides in the Synthesis of 2-Amino-1,3,4-oxadiazoles

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Sarah J. Dolman,*^† Francis Gosselin,^† Paul D. O'Shea,^† and Ian W. Davies^‡

Department of Process Research, Merck Frosst Centre for Therapeutic Research, 16711 Route Transcanadienne, Kirkland, Qubec, Canada H9H 3L1, and Department of Process Research, Merck Research Laboratories, P.O. Box 2000, Rahway, New Jersey 07065 sarah_dolman@merck.com

J. Org. Chem., 2006, 71 (25), pp 9548–9551

DOI: 10.1021/jo0618730

Publication Date (Web): November 15, 2006

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

†

Merck Frosst Centre for Therapeutic Research.

‡

Merck Research Laboratories.

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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Published In Issue December 08, 2006
Received September 11, 2006

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Superior Reactivity of Thiosemicarbazides in the Synthesis of 2-Amino-1,3,4-oxadiazoles

Abstract

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SciFinder Links

History

Recommend & Share

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