A Copper-Catalyzed Interrupted Domino Reaction for the Synthesis of Fused Triazolyl Benzothiadiazine-1-oxides

被引：3

作者：

Hommelsheim, Rene ^{[1
]}

Bausch, Sandra ^{[1
]}

Selvakumar, Arjuna ^{[1
]}

Amer, Mostafa M. ^{[1
,2
]}

Truong, Khai-Nghi ^{[3
]}

Rissanen, Kari ^{[3
]}

Bolm, Carsten ^{[1
]}

机构：

[1] Rhein Westfal TH Aachen, Inst Organ Chem, Landoltweg 1, D-52074 Aachen, Germany

[2] Egyptian Petr Res Inst, Cairo 11727, Egypt

[3] Univ Jyvaskyla, Dept Chem, POB 35, Survontie 9 B, Jyvaskyla 40014, Finland

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2023年 / 29卷 / 13期

关键词：

CLICK; copper catalysis; cycloaddition; domino reactions; sulfoximines; sulfur heterocycles; ONE-POT SYNTHESIS; CLICK CHEMISTRY; ORGANIC AZIDES; HETEROCYCLIC CHEMISTRY; NITROGEN-HETEROCYCLES; ARYLATION SEQUENCE; TERMINAL ALKYNES; NATURAL-PRODUCTS; SULFOXIMINES; 1,2,3-TRIAZOLES;

D O I：

10.1002/chem.202203729

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Copper(I)-catalyzed domino reactions of 2-azido sulfoximines with 1-iodoalkynes yield fused triazolyl-containing benzothiadiazine-1-oxides. The protocol features the synthesis of two fused heterocyclic rings in one step with good to excellent yields and a broad functional group tolerance. Detailed mechanistic investigations indicate that a copper pi-complex initiates a cycloaddition and oxidative C-N coupling reaction sequence. The results suggest an interrupted domino process involving an iodinated triazole as a key intermediate.

引用

页数：7

共 50 条

[31] Copper-catalyzed domino reaction between 1-(2-halophenyl) methanamines and amidines or imidates for the synthesis of 2-substituted quinazolines
Omar, Mohamed A.
Conrad, Juergen
Beifuss, Uwe
TETRAHEDRON, 2014, 70 (18) : 3061 - 3072
[32] Copper-Catalyzed Selective Synthesis of Highly Substituted Pyridones by the Reaction of Enaminones with Alkynes
Shao, Yushang
Yao, Wenjuan
Liu, Jun
Zhu, Kai
Li, Yanzhong
SYNTHESIS-STUTTGART, 2012, 44 (21): : 3301 - 3306
[33] Mild and efficient synthesis of propargylamines by copper-catalyzed Mannich reaction
Bieber, LW
da Silva, MF
TETRAHEDRON LETTERS, 2004, 45 (45) : 8281 - 8283
[34] Synthesis of fused 1,2,3-triazolo-1,3,6-triazonines through copper-catalyzed intramolecular Ullmann cross-coupling reaction
do Nascimento, Jose Edmilson R.
Goncalves, Loren C. C.
Hooyberghs, Geert
Van der Eycken, Erik V.
Alves, Diego
Lenardao, Eder J.
Perin, Gelson
Jacob, Raquel G.
TETRAHEDRON LETTERS, 2016, 57 (44) : 4885 - 4889
[35] Copper-Catalyzed Domino Oxidation-Acyloxylation Reaction of 2-Arylpyridines with Aldehydes or Methylarenes
Bian, Yong-Jun
Xiang, Chang-Bing
Chen, Zhi-Ming
Huang, Zhi-Zhen
SYNLETT, 2011, (16) : 2407 - 2409
[36] Copper-Catalyzed C-Arylation and Denitrogenation of Tetrazoles: Domino Synthesis of 1,3-Diaminoisoquinoline Derivatives
Shi, Liangliang
Yang, Haijun
Jiang, Yuyang
Fu, Hua
ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (06) : 1177 - 1184
[37] Copper-catalyzed one-pot synthesis of glycosylated iminocoumarins and 3-triazolyl-2-iminocoumarins
Mandal, Pintu Kumar
RSC ADVANCES, 2014, 4 (11) : 5803 - 5814
[38] Copper-catalyzed the coupling reaction of sulfonylazides with formamides for the synthesis of N-sulfonyl amidines
Ma, Guoyang
Xia, Ran
Li, Yawen
Xu, Shaohong
TETRAHEDRON, 2024, 153
[39] Copper-Catalyzed Cascade Multicomponent Reaction of Azides, Alkynes, and Selenium: Synthesis of Ditriazolyl Diselenides
Sun, Bo-Xun
Wang, Xu-Nan
Fan, Tai-Gang
Hou, Yu-Jian
Shen, Yun-Tao
Li, Ya-Min
JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (07) : 4528 - 4535
[40] Chemodivergent synthesis of multi-substituted/fused pyrroles via copper-catalyzed carbene cascade reaction of propargyl α-iminodiazoacetates
Zhang, Cheng
Chang, Sailan
Qiu, Lihua
Xu, Xinfang
CHEMICAL COMMUNICATIONS, 2016, 52 (84) : 12470 - 12473

← 1 2 3 4 5 →