Silver(I)- and Base-Mediated formal [4+3] Cycloaddition of in Situ generated 1,2-Diaza-1,3-dienes with C,N-Cyclic Azomethine Imines: An Efficient Protocol for the Synthesis of Tetrazepine Derivatives

被引：14

作者：

Li, Zefei ^{[1
]}

Li, Shuaikang ^{[1
]}

Kan, Tianjiao ^{[1
]}

Wang, Xinyue ^{[1
]}

Xin, Xin ^{[1
]}

Hou, Yunlei ^{[1
]}

Gong, Ping ^{[1
]}

机构：

[1] Shenyang Pharmaceut Univ, Sch Pharmaceut Engn, 103 Wenhua Rd, Shenyang 110016, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2020年 / 362卷 / 13期

关键词：

Silver; 1,2-Diaza-1,3-dienes; Azomethine imines; 4+3] Cycloaddition; Tetrazepine derivatives; SILVER(I)-RHODIUM(I) COOPERATIVE CATALYSIS; INTERMOLECULAR 5+2 CYCLOADDITION; GAMMA-SUBSTITUENT ALLENOATES; ALPHA-HALOGENO HYDRAZONES; RING-CLOSURE REACTIONS; DIELS-ALDER REACTION; ASYMMETRIC-SYNTHESIS; 1,3-DIPOLAR CYCLOADDITIONS; TANDEM REACTION; SULFUR YLIDES;

D O I：

10.1002/adsc.202000398

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A silver(I)- and base-mediated formal [4+3] cycloaddition reaction of in situ generated 1,2-diaza-1,3-dienes with in situ formed C,N-cyclic azomethine imines has been developed. This protocol provided an efficient method for the synthesis of biologically important 1,2,4,5-tetrazepine derivatives with a wild substrate scope and excellent functional group tolerance in moderate to excellent yields.

引用

页码：2626 / 2631

页数：6

共 11 条

[1] [4+3] Cycloaddition of in situ generated azoalkenes with C,N-cyclic azomethine imines: efficient synthesis of tetrazepine derivatives
Hu, Xiao-Qiang
Chen, Jia-Rong
Gao, Shuang
Feng, Bin
Lu, Liang-Qiu
Xiao, Wen-Jing
CHEMICAL COMMUNICATIONS, 2013, 49 (72) : 7905 - 7907
[2] Base-mediated diastereoselective [4+3] annulation of in situ generated ortho-quinone methides with C, N-cyclic azomethine imines
Xu, Jianfeng
Yuan, Shiru
Peng, Jingyi
Miao, Maozhong
Chen, Zhengkai
Ren, Hongjun
ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (36) : 7513 - 7517
[3] Silver(I)- and Base-Mediated [3+3]-Cycloaddition of C,N-Cyclic Azomethine Imines with Aza-oxyallyl Cations
Cheng, Xiao
Cao, Xia
Xuan, Jun
Xiao, Wen-Jing
ORGANIC LETTERS, 2018, 20 (01) : 52 - 55
[4] Synthesis of Tetrahydropyridazine Amino Acid Derivatives by a Formal [4+2] Cycloaddition Reaction of 1,2-Diaza-1,3-dienes with Dehydroalanine Esters
Attanasi, Orazio A.
Favi, Gianfranco
Giorgi, Gianluca
Mantellini, Fabio
Moscatelli, Giada
Piersanti, Giovanni
CURRENT ORGANIC SYNTHESIS, 2013, 10 (05) : 803 - 811
[5] Formal [4+1] cycloaddition of in situ generated 1,2-diaza-1,3-dienes with diazo esters: facile approaches to dihydropyrazoles containing a quaternary center
Chen, Bo
Chu, Wen-Dao
Liu, Quan-Zhong
RSC ADVANCES, 2019, 9 (03) : 1487 - 1490
[6] Synthesis of functionalized tetrahydropyridazines via catalyst-free self [4+2] cycloaddition of in situ generated 1,2-diaza-1,3-dienes
Zhang, Zhimin
Zhang, Li
Chen, Qingqing
Lu, Tao
Zhou, Qingfa
RSC ADVANCES, 2016, 6 (66) : 61680 - 61685
[7] An efficient [4+3] cycloaddition reaction of aza-o-quinodimethanes with C,N-cyclic azomethine imines: stereoselective synthesis of 1,2,4-triazepines
Chen, L.
Yang, G. M.
Wang, J.
Jia, Q. F.
Wei, J.
Du, Z. Y.
RSC ADVANCES, 2015, 5 (94): : 76696 - 76699
[8] Synthesis of spiropyrazoline oxindoles by a formal [4+1] annulation reaction between 3-bromooxindoles and in situ-derived 1,2-diaza-1,3-dienes
Chen, Dong-Zhen
Xiao, Wen-Jing
Chen, Jia-Rong
ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (07): : 1289 - 1293
[9] PIDA-mediated oxidative aromatic C-N bond cleavage: Efficient methodology for the synthesis of 1,2-diaza-1,3-dienes under ambient conditions
Kumar, Abhishek
Katiyar, Sarita
Jaiswal, Arvind Kumar
Kant, Ruchir
V. Sashidhara, Koneni
TETRAHEDRON LETTERS, 2021, 77
[10] A [4+3] Cycloaddition Reaction of Aza-ortho-quinone Methides with C,N-Cyclic Azomethine Imines for Synthesis of 1,2,4-Triaze-pines
Wang, Xinyue
Li, Zefei
Feng, Chang
Zhen, Qi
Guo, Mingzhang
Hou, Yunlei
Gong, Ping
SYNLETT, 2021, 32 (20) : 2090 - 2096

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