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Schneider Y, Prévost J, Gobin M, et al. Diazirines as potent electrophilic nitrogen sources: application to the synthesis of pyrazoles. Org Lett. 2013;16(2):596-9doi: 10.1021/ol403495e.
Schneider, Y., Prévost, J., Gobin, M., & Legault, C. Y. (2014). Diazirines as potent electrophilic nitrogen sources: application to the synthesis of pyrazoles. Organic letters, 16(2), 596-9. https://doi.org/10.1021/ol403495e
Schneider, Yoann, et al. "Diazirines as potent electrophilic nitrogen sources: application to the synthesis of pyrazoles." Organic letters vol. 16,2 (2014): 596-9. doi: https://doi.org/10.1021/ol403495e
Schneider Y, Prévost J, Gobin M, Legault CY. Diazirines as potent electrophilic nitrogen sources: application to the synthesis of pyrazoles. Org Lett. 2014 Jan 17;16(2):596-9. doi: 10.1021/ol403495e. Epub 2013 Dec 30. PMID: 24378081.
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Org Lett. 2014 Jan 17;16(2):596-9. doi: 10.1021/ol403495e. Epub 2013 Dec 30.

Diazirines as potent electrophilic nitrogen sources: application to the synthesis of pyrazoles.

Organic letters

Yoann Schneider, Julie Prévost, Maëlle Gobin, Claude Y Legault

Affiliations

  1. University of Sherbrooke , Department of Chemistry, 2500 boul. de l'Université, Sherbrooke, Québec J1K 2R1, Canada.

PMID: 24378081 DOI: 10.1021/ol403495e

Abstract

Even after more than 50 years since its discovery, the electrophilic potential of diazirines was never truly exploited. This longstanding limitation has been resolved. N-Monosubstituted diaziridines and hydrazones are obtained by nucleophilic additions. They release, under hydrolysis conditions, the corresponding monosubstituted hydrazines. The latter were converted to pyrazoles in high yields. The adamantanone can be recovered in 80-100% yields. This work demonstrates the potential of diazirines as electrophilic nitrogen sources with recoverable protecting groups.

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