Cyclization of protected N-acylhydroxyguanidine to 3-amino-1,2,4-oxadiazole |
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Authors: | Jamie B Côté Andrew RoughtonJoanna Nasielski Jeff WilsonJi Chang You Judd M Berman |
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Institution: | a Dalton Medicinal Chemistry Inc., 349 Wildcat Road, Toronto, Ontario, Canada M3J 2S3 b National Research Laboratory of Molecular Virology, Department of Pathology, College of Medicine, The Catholic University of Korea and Avixgen Inc., Seocho-gu Banpo-dong 505, Seoul 137-701, Republic of Korea |
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Abstract: | The acid mediated cyclization of a protected N-acylhydroxyguanidine into the corresponding 3-amino-1,2,4-oxadiazole and confirmation of its structure by single crystal X-ray crystallography is reported herein. The yield of the cyclization is comparable to literature reports utilizing alternative procedures. Importantly, these new conditions provide complementary chemoselectivity to current synthetic procedures which may be useful for the synthesis of 3-amino-1,2,4-oxadiazoles in general. |
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Keywords: | N-Acylhydroxyguanidine 3-Amino-1 2 4-oxadiazole Acylthiourea Cyclization Heterocycle |
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