Copper-catalyzed domino synthesis of nitrogen heterocycle-fused benzoimidazole and 1,2,4-benzothiadiazine 1,1-dioxide derivatives

Daoshan Yang; Baojuan An; Wei Wei; Laijin Tian; Ben Huang; Hua Wang

doi:10.1021/co500125n

Copper-catalyzed domino synthesis of nitrogen heterocycle-fused benzoimidazole and 1,2,4-benzothiadiazine 1,1-dioxide derivatives

ACS Comb Sci. 2015 Feb 9;17(2):113-9. doi: 10.1021/co500125n. Epub 2015 Jan 16.

Authors

Daoshan Yang¹, Baojuan An, Wei Wei, Laijin Tian, Ben Huang, Hua Wang

Affiliation

¹ The Key Laboratory of Life-Organic Analysis and Key Laboratory of Pharmaceutical Intermediates and Analysis of Natural Medicine, School of Chemistry and Chemical Engineering, Qufu Normal University , Qufu 273165, Shandong China.

PMID: 25549532
DOI: 10.1021/co500125n

Abstract

A convenient copper-catalyzed domino method for the synthesis of nitrogen heterocycle-fused benzoimidazole and 1,2,4-benzothiadiazine 1,1-dioxides has been developed using readily available 2-bromo-N-phenylbenzenesulfonamides and benzimidazole derivatives as the starting materials. The domino process comprises an Ullmann-type N-arylation and intramolecular C-H amination. The inexpensive and efficient copper-catalyzed method should provide a new and useful strategy for for constructing novel, biologically interesting heterocycles containing benzoimidazole and 1,2,4-benzothiadiazine 1,1-dioxide motifs.

Keywords: 1,2,4-benzothiadiazine 1,1-dioxide; N-heterocycle; benzimidazole; copper-catalyzed; domino reaction.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Benzothiadiazines / chemistry*
Catalysis
Copper / chemistry*
Cyclic S-Oxides / chemistry*
Heterocyclic Compounds / chemical synthesis*
Heterocyclic Compounds / chemistry
Molecular Structure
Nitrogen / chemistry*

Substances

Benzothiadiazines
Cyclic S-Oxides
Heterocyclic Compounds
Copper
Nitrogen