Transition-Metal-Free Annulation of Enamines and Tosyl Azide toward N-Heterocycle Fused and 5-Amino-1,2,3-Triazoles

被引：9

作者：

Deng, Leiling ^{[1
]}

Liu, Yunyun ^{[1
]}

Zhu, Yanping ^{[2
]}

Wan, Jie-Ping ^{[1
]}

机构：

[1] Jiangxi Normal Univ, Coll Chem & Chem Engn, Nanchang 330022, Jiangxi, Peoples R China

[2] Yantai Univ, Sch Pharm, Key Lab Mol Pharmacol & Drug Evaluat, Minist Educ,Collaborat Innovat Ctr Adv Drug Deliv, Yantai 264005, Peoples R China

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 2020卷 / 34期

基金：

中国国家自然科学基金;

关键词：

Enamines; Tosyl azide; N-Side chains; 1; 2; 3-Triazole; Synthesis design; 1,3-DIPOLAR CYCLOADDITION REACTION; REGIOSELECTIVE SYNTHESIS; 1,4-DISUBSTITUTED 1,2,3-TRIAZOLES; SUBSTITUTED 1,2,3-TRIAZOLES; ALKYNE CYCLOADDITION; DOMINO REACTIONS; BOND FORMATION; DIRECT ACCESS; FREE ROUTE; DERIVATIVES;

D O I：

10.1002/ejoc.202000938

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The annulation reactions betweengem-diamino enaminones (ketene aminals) and tosyl azide providing N-heterocycle fused and 5-amino side chain functionalized 1,2,3-triazoles have been developed. The synthesis of these N-side chain functionalized 1,2,3-triazoles has been executed with high efficiency and broad synthetic scope under transition metal-free conditions with the assistance of NaHCO(3)only.

引用

页码：5606 / 5609

页数：4

共 22 条

[1] Transition-metal-free synthesis of 5-amino-1,2,3-triazoles via nucleophilic addition/cyclization of carbodiimides with diazo compounds
Wang, Shilong
Zhang, Yuanyuan
Liu, Guixin
Xu, Hui
Song, Lijuan
Chen, Jinchun
Li, Jiazhu
Zhang, Zhen
[J]. ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (03) : 599 - 604
[2] Metal-Free Synthesis of 1,2,3-Triazoles in Pure Water via the Enamine Modified Annulation Reactions with Tosyl Azide
Zheng, Xixi
Liu, Yunyuna
Wan, Jie-Ping
[J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2021, 41 (07) : 2700 - 2706
[3] Transition-Metal-Free Catalytic Synthesis of 1,5-Diaryl-1,2,3-triazoles
Kwok, Sen W.
Fotsing, Joseph R.
Fraser, Rebecca J.
Rodionov, Valentin O.
Fokin, Valery V.
[J]. ORGANIC LETTERS, 2010, 12 (19) : 4217 - 4219
[4] Fused Tetrazoles as Azide Surrogates in Click Reaction: Efficient Synthesis of N-Heterocycle-Substituted 1,2,3-Triazoles
Chattopadhyay, Buddhadeb
Vera, Claudia I. Rivera
Chuprakov, Stepan
Gevorgyan, Vladimir
[J]. ORGANIC LETTERS, 2010, 12 (09) : 2166 - 2169
[5] Synthesis of β-triazolylenones via metal-free desulfonylative alkylation of N-tosyl-1,2,3-triazoles
Pati, Soumyaranjan
Almeida, Renata G.
da Silva Junior, Eufranio N.
Namboothiri, Irishi N. N.
[J]. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2021, 17 : 762 - 770
[6] Transition metal free selective N2-arylation of 1,2,3-triazoles
Roshandel, Sahar
Lunn, Maiko
Suri, Suresh
Prakash, Surya
[J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2019, 258
[7] CYCLO-ADDITION OF AROYL-ACYLKETENE S,N-ACETALS WITH TOSYL AZIDE - SYNTHESIS OF NOVEL 4-AROYL-ACYL-5-AMINO-1H-1,2,3-TRIAZOLES AND 3,4-ANNULATED 1,2,3-TRIAZOLES
CHAKRASALI, RT
ILA, H
JUNJAPPA, H
[J]. SYNTHESIS-STUTTGART, 1988, (11): : 851 - 854
[8] A Metal- and Azide-Free Multicomponent Assembly toward Regioselective Construction of 1,5-Disubstituted 1,2,3-Triazoles
Wan, Jie-Ping
Cao, Shuo
Liu, Yunyun
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (18): : 9028 - 9033
[9] Designing a new basic ionic liquid [DHIM][OH] as a task specific bifunctional catalyst for facile microwave assisted metal free synthesis of 5-amino-1,2,3-triazoles
Dutta, Bidyutjyoti
Garg, Anirban
Phukan, Parmita
Kulshrestha, Akshay
Kumar, Arvind
Sarma, Diganta
[J]. NEW JOURNAL OF CHEMISTRY, 2021, 45 (29) : 12792 - 12797
[10] Transition-metal-free S-N bond formation: synthesis of 5-amino-1,2,4-thiadiazoles from isothiocyanates and amidines
Yang, Zan
Cao, Ting
Liu, Si
Li, An
Liu, Kun
Yang, Tao
Zhou, Congshan
[J]. NEW JOURNAL OF CHEMISTRY, 2019, 43 (17) : 6465 - 6468

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