Annulation Reactions of In-Situ-Generated N‑(Het)aroyldiazenes with Isothiocyanates Leading to 2‑Imino-1,3,4-oxadiazolines

A novel annulation reaction of N-(het)­aroyldiazenes and isothiocyanates has been established. This transformation involves a sequential cyclization and desulfurization/intramolecular rearrangement to produce 2-imino-1,3,4-oxadiazolines. The less-stable N-(het)­aroyldiazenes can be conveniently gene...

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Published inOrganic letters Vol. 21; no. 1; pp. 210 - 213
Main Authors Zhao, Qiongli, Ren, Linning, Hou, Jiao, Yu, Wenquan, Chang, Junbiao
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 04.01.2019
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CYCLOADDITION
AMINATION
HYDRAZIDES
N-ACYLDIAZENES
AEROBIC OXIDATION
DERIVATIVES
ACCESS
UREAS
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Summary:A novel annulation reaction of N-(het)­aroyldiazenes and isothiocyanates has been established. This transformation involves a sequential cyclization and desulfurization/intramolecular rearrangement to produce 2-imino-1,3,4-oxadiazolines. The less-stable N-(het)­aroyldiazenes can be conveniently generated in situ by I2-mediated oxidation of hydrazides, which allows a one-pot synthesis of the products directly from readily accessible hydrazide and isothiocyanate substrates. This operationally simple synthetic process requires no use of malodorous isocyanides and can be conveniently conducted on a gram scale.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.8b03663