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

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