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

被引：27

作者：

Zhao, Qiongli ^{[1
]}

Ren, Linning ^{[1
]}

Hou, Jiao ^{[1
]}

Yu, Wenquan ^{[1
]}

Chang, Junbiao ^{[1
]}

机构：

[1] Zhengzhou Univ, Sch Pharmaceut Sci, Collaborat Innovat Ctr New Drug Res & Safety Eval, Coll Chem & Mol Engn, Zhengzhou 450001, Henan, Peoples R China

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 01期

基金：

中国国家自然科学基金;

关键词：

AEROBIC OXIDATION; N-ACYLDIAZENES; DERIVATIVES; HYDRAZIDES; CYCLOADDITION; AMINATION; ACCESS; UREAS;

D O I：

10.1021/acs.orglett.8b03663

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 I-2-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.

引用

页码：210 / 213

页数：4

共 5 条

[1] Synthesis of 2-Imino-1,3,4-oxadiazolines from Acylhydrazides and Isothiocyanates via Aerobic Oxidation and a DMAP-Mediated Annulation Sequence
Lim, Jae Hyeok
Baek, Sang Eun
Lad, Bapurao Sudam
Kim, Jinho
ACS OMEGA, 2022, 7 (32): : 28148 - 28159
[2] Synthesis of 2-Imino-1,3,4-Selenadiazoles via Tributylphosphine-Mediated Annulation of N-Aroyldiazenes with Isoselenocyanates
Huang, Zhengyan
Zhang, Qianqian
Yi, Xiaofei
Zhao, Zongxiang
Yu, Wenquan
Chang, Junbiao
ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (21) : 4894 - 4898
[3] Synthesis of 2-Imino-1,3,4-thiadiazoles from Hydrazides and Isothiocyanates via Sequential Oxidation and P(NMe2)3 -Mediated Annulation Reactions
Huang, Zhengyan
Zhang, Qianqian
Zhao, Qiongli
Yu, Wenquan
Chang, Junbiao
ORGANIC LETTERS, 2020, 22 (11) : 4378 - 4382
[4] Reaction of 2-diazo-1,2-diarylethanones with benzophenone N-(diaryl)acylhydrazones:: Formation of 1,3,4-Oxadiazolines
Singh, Girija S.
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2006, 43 (06) : 1653 - 1656
[5] Investigation of reactions of CH-acids with generated in situ N-[1,2-bis(methoxycarbonyl)vinyl]pyridinium in the synthesis of 1,2,3,4,5,6,7-hepta(methoxycarbonyl)cycloheptatriene
Belyy, A. Yu.
Sokolova, A. D.
Salikov, R. F.
Platonov, D. N.
Tomilov, Yu. V.
RUSSIAN CHEMICAL BULLETIN, 2024, 73 (05) : 1455 - 1459

← 1 →