ACID PROMOTED METAL FREE SYNTHESIS OF TRIAZOLE-FUSED HETEROCYCLES VIA INTRAMOLECULAR [3+2] CYCLOADDITION

被引：1

作者：

Zhang, Youlai ^{[1
]}

Wang, Mengdi ^{[1
]}

Li, Junru ^{[1
]}

Di, Qingtong ^{[1
]}

Tian, Ziye ^{[1
]}

Chen, Baoquan ^{[1
]}

Zhang, Huan ^{[1
]}

Tanimoto, Hiroki ^{[2
]}

Morimoto, Tsumoru ^{[2
]}

Kakiuchi, Kiyomi ^{[2
]}

机构：

[1] Tianjin Univ Technol, Sch Chem & Chem Engn, Tianjin Key Lab Organ Solar Cells & Photochem Con, Tianjin 300384, Peoples R China

[2] Nara Inst Sci & Technol NAIST, Grad Sch Mat Sci, 8916-5 Takayama, Nara 6300192, Japan

来源：

HETEROCYCLES | 2018年 / 96卷 / 05期

基金：

中国国家自然科学基金;

关键词：

Triazole-Fused Heterocycle; Cycloaddition Reaction; Azide; CLICK CHEMISTRY; 1,2,3-TRIAZOLES; DERIVATIVES; INHIBITOR; ACCESS;

D O I：

10.3987/COM-18-13900

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A practical and efficient protocol for the synthesis of triazole-fused heterocycles through intramolecular metal free [3+2] azide-alkyne cycloaddition reaction is described. Range of acids was selected to demonstrate the reaction conditions. Organic azides and propargyl cations generated by acids gave fused triazoles including multivariate rings and heterocycles. Various fused triazoles and bistriazoles were obtained in good yields under mild reaction conditions.

引用

页码：947 / 957

页数：11

共 50 条

[1] Synthesis of triazole-fused tetracyclic spirooxindole derivatives via metal-free Huisgen cycloaddition
Maiti, Sandip
Parui, Nabin
Halder, Joydev
Dash, Jyotirmayee
CHEMICAL COMMUNICATIONS, 2024, 60 (73) : 10009 - 10012
[2] Metal-Free Tandem Approach for Triazole-Fused Diazepinone Scaffolds via [3+2]Cycloaddition/C-N Coupling Reaction
Majeed, Kashif
Wang, Lingna
Liu, Bangjie
Guo, Zijian
Zhou, Fengtao
Zhang, Qiuyu
JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (01): : 207 - 222
[3] Metal Free Domino β-Azidation/[3+2] Cycloaddition Reaction for the Synthesis of 1,2,3-Triazole-Fused Dihydrobenzoxazinones
Donikela, Sangeetha
Mainkar, Prathama S.
Nayani, Kiranmai
Chandrasekhar, Srivari
JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (16): : 10546 - 10553
[4] Synthesis of 1,2,3-Triazole-Fused Heterocycles via Intramolecular Azide-Alkyne Cycloaddition Reactions
Majumdar, Krishna C.
Ray, Krishanu
SYNTHESIS-STUTTGART, 2011, (23): : 3767 - 3783
[5] Facile Access to Triazole-Fused 3,1-Benzoxazines Enabled by Metal-Free Base-Promoted Intramolecular C-O Coupling
Tatevosyan, Stepan S.
Kotovshchikov, Yury N.
Latyshev, Gennadij, V
Lukashev, Nikolay, V
Beletskaya, Irina P.
SYNTHESIS-STUTTGART, 2022, 54 (02): : 369 - 377
[6] Intramolecular Huisgen [3+2] cycloaddition in water: synthesis of fused pyrrolidine-triazoles
Kumar, Indresh
Mir, Nisar A.
Rode, Chandrashaker V.
Wakhloo, Basant P.
TETRAHEDRON-ASYMMETRY, 2012, 23 (3-4) : 225 - 229
[7] Stereocontrolled Synthesis of (±)-Melokhanine E via an Intramolecular Formal [3+2] Cycloaddition
Cholewczynski, Anna E.
Williams, Peyton C.
Pierce, Joshua G.
ORGANIC LETTERS, 2020, 22 (02) : 714 - 717
[8] Expedient Synthesis of N-Fused Indoles through an Intramolecular [3+2]-Cycloaddition Approach
Kathiravan, Subban
Raghunathan, Raghavachary
SYNLETT, 2010, (06) : 952 - 954
[9] Base-Promoted Synthesis of N-H Free Pyrroles via net [3+2]-Cycloaddition
Jin, Huimin
Zhou, Fan
Xiang, Zhenhua
Chen, Lingfeng
Liang, Guang
Walsh, Patrick J.
Li, Jie
ADVANCED SYNTHESIS & CATALYSIS, 2024, 366 (04) : 942 - 947
[10] A transition-metal-free azide-alkyne cycloaddition/hydroamination cascade reaction for the construction of triazole-fused piperazin-2-ones
Qiu, Kongxi
Wu, Kaifu
Ma, Haowen
Ao, Yunlin
Zhou, Wei
Cai, Qian
ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 22 (06) : 1176 - 1180

← 1 2 3 4 5 →