Site-Selective Conversion of Azido Groups at Carbonyl α-Positions to Diazo Groups in Diazido and Triazido Compounds

Taiki Yokoi, Hiroki Tanimoto*, Tomomi Ueda, Tsumoru Morimoto, Kiyomi Kakiuchi

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

26 Scopus citations

Abstract

This paper reports on the selective conversion of alkyl azido groups at the carbonyl α-position to diazo compounds. Through β-elimination of dinitrogen, followed by hydrazone formation/decomposition, α-azidocarbonyl moieties were transformed into α-diazo carbonyl groups in one step. As these reaction conditions do not involve aryl or general alkyl azides, site-selective conversions of di- and triazides were achieved. Through this method, the successive site-selective conjugation of the triazido molecule with three different components is demonstrated.

Original languageEnglish
Pages (from-to)12103-12121
Number of pages19
JournalJournal of Organic Chemistry
Volume83
Issue number19
DOIs
StatePublished - 2018/10/05

ASJC Scopus subject areas

  • Organic Chemistry

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