Novel acid-catalyzed rearrangement of tetrahydro-1,2,3,4-tetrazines: Unexpected formation of glycosazones

Martín Avalos, Reyes Babiano, Pedro Cintas, Fernando R. Clemente, Ruth Gordillo, Michael B. Hursthouse, José L. Jiménez, Mark E. Light, Juan C. Palacios

Research output: Contribution to journalArticle

7 Scopus citations

Abstract

The present contribution discloses a simple and unexpected acid-catalyzed cleavage of tetrahydrotetrazines leading to 1,2-bis(hydrazones). Incorporation of a chiral fragment derived from carbohydrates enables the rapid preparation of glycosazones, a family of compounds employed by Emil Fischer to elucidate the configuration of sugars. In addition, a mechanistic proposal accounts for experimental observations.

Original languageEnglish (US)
Pages (from-to)2378-2381
Number of pages4
JournalJournal of Organic Chemistry
Volume67
Issue number7
DOIs
Publication statusPublished - Apr 5 2002

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ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Avalos, M., Babiano, R., Cintas, P., Clemente, F. R., Gordillo, R., Hursthouse, M. B., ... Palacios, J. C. (2002). Novel acid-catalyzed rearrangement of tetrahydro-1,2,3,4-tetrazines: Unexpected formation of glycosazones. Journal of Organic Chemistry, 67(7), 2378-2381. https://doi.org/10.1021/jo0163391