Two reaction modes of 1-sulfonyl-1,2,3-triazoles and pyridinium 1,4-zwitterionic thiolates: catalyst-free synthesis of pyrido[1,2-a]pyrazine derivatives and 1,4-thiazine derivatives

被引：19

作者：

Duan, Shengguo ^{[1
]}

Chen, Cong ^{[1
]}

Chen, Yidian ^{[1
]}

Jie, Yuchen ^{[1
]}

Luo, Huan ^{[1
]}

Xu, Ze-Feng ^{[1
]}

Cheng, Bin ^{[2
]}

Li, Chuan-Ying ^{[1
]}

机构：

[1] Zhejiang Sci Tech Univ, Dept Chem, Key Lab Surface & Interface Sci Polymer Mat Zheji, Hangzhou 310018, Peoples R China

[2] Shenzhen Polytech, Inst Marine Biomed, Shenzhen 518055, Peoples R China

来源：

ORGANIC CHEMISTRY FRONTIERS | 2021年 / 8卷 / 24期

基金：

中国国家自然科学基金;

关键词：

HETEROCYCLES; TRANSANNULATION; 1,2,3-TRIAZOLES; REARRANGEMENT; INDOLIZINES; TRIAZOLES;

D O I：

10.1039/d1qo01237a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Two reaction modes of 1-sulfonyl-1,2,3-triazoles and pyridinium 1,4-zwitterionic thiolates were described. Pyrido[1,2-a]pyrazine derivatives were obtained in moderate yields when 4-OEt substituted triazoles were employed in reactions, and 1,4-thiazine derivatives were synthesized when 4-NPhth substituted triazoles were employed. The mechanism may involve a sulfur migration via an addition/elimination process which has never been reported in the previous pyridinium 1,4-zwitterionic thiolate related works.

引用

页码：6962 / 6967

页数：6

共 48 条

[1] Mild Aminoacylation of Indoles and Pyrroles through a Three-Component Reaction with Ynol Ethers and Sulfonyl Azides
Alford, Joshua S.
Davies, Huw M. L.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (29) : 10266 - 10269
[2] Expanding the Scope of Donor/Acceptor Carbenes to N-Phthalimido Donor Groups: Diastereoselective Synthesis of 1-Cyclopropane α-Amino Acids
Alford, Joshua S.
Davies, Huw M. L.
[J]. ORGANIC LETTERS, 2012, 14 (23) : 6020 - 6023
[3] Recent Advances in Transition-Metal-Catalyzed Denitrogenative Transformations of 1,2,3-Triazoles and Related Compounds
Anbarasan, Pazhamalai
Yadagiri, Dongari
Rajasekar, Shanmugam
[J]. SYNTHESIS-STUTTGART, 2014, 46 (22): : 3004 - 3023
[4] [Anonymous], 2018, HYGEIA J DRUGS MED
[5] Revision of outcome and mechanism of a new multicomponent reaction
Carballares, S
Espinosa, JF
[J]. ORGANIC LETTERS, 2005, 7 (12) : 2329 - 2331
[6] Synthesis of α-cyano sulfone via thermal rearrangement of 1,4-disubstituted triazole mediated by carbene and radical species
Cen, Mengjie
Xiang, Qiaoyi
Xu, Yiwen
Duan, Shengguo
Lv, Yaohong
Xu, Ze-Feng
Li, Chuan-Ying
[J]. ORGANIC CHEMISTRY FRONTIERS, 2020, 7 (03): : 596 - 601
[7] Transition-Metal-Catalyzed Denitrogenative Transannulation: Converting Triazoles into Other Heterocyclic Systems
Chattopadhyay, Buddhadeb
Gevorgyan, Vladimir
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (04) : 862 - 872
[8] Use of praziquantel for clinical treatment and morbidity control of schistosomiasis japonica in China: a review of 30 years' experience
Chen, MG
[J]. ACTA TROPICA, 2005, 96 (2-3) : 168 - 176
[9] Synthesis of Pyridothiazepines via a 1,5-Dipolar Cycloaddition Reaction between Pyridinium 1,4-Zwitterionic Thiolates and Activated Allenes
Cheng, Bin
Zhang, Xinping
Li, Hui
He, Yixuan
Li, Yun
Sun, Haiyan
Wang, Taimin
Zhai, Hongbin
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (21) : 4668 - 4672
[10] Synthesis of indolizines from pyridinium 1,4-zwitterionic thiolates and propiolic acid derivatives via a formal [4+1] pathway
Cheng, Bin
Li, Hui
Duan, Shengguo
Zhang, Xinping
He, Yixuan
Li, Yuntong
Li, Yun
Wang, Taimin
Zhai, Hongbin
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (32) : 6253 - 6257

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