Benzazoles: II. Synthesis and arenesulfonylation of 1-methyl-1H-benzimidazol-2-amine

Kaipnazarov, T. N.; Mukhamedov, N. S.; Okmanov, R. Ya.; Berdimbetova, G. E.; Zhonkhozhaeva, F. B.

doi:10.1134/s1070428013120063

Russ J Org Chem

2013

DOI: 10.1134/s1070428013120063

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Benzazoles: II. Synthesis and arenesulfonylation of 1-methyl-1H-benzimidazol-2-amine

T. N. Kaipnazarov

N. S. Mukhamedov

R. Ya. Okmanov

et al.

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Cited by 3 publications

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Synthesis of Cyclohexenone(aryl)iodonium Salts and Their Application in Construction of Fused aza‐Heterocyclic Skeletons

Zhang,

Xu,

et al. 2024

Adv Synth Catal

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A class of cyclohexenone(aryl)iodonium salts was readily prepared from 2‐iodocyclohexenones and arenes under mild conditions. This novel series of hypervalent iodonium building blocks exhibits dual characteristics of hyperiodonium salts and α,β‐unsaturated cyclic ketones, enabling access to intricate aza‐heterocycles. The reaction of these cyclohexenone(aryl)iodonium salts with arylamines and benzene sulfonamides affords 2‐acylaziridines, while with 1H‐imidazol‐2‐amines leads to the formation of the 1H‐imidazoimidazole‐fused compounds. The transformation is postulated to proceed through an exclusive hyperiodonium‐mediated N‐Michael addition followed by N‐annulation cascade.

show abstract

Synthesis of Cyclohexenone(aryl)iodonium Salts and Their Application in Construction of Fused aza‐Heterocyclic Skeletons

Zhang,

Xu,

et al. 2024

Adv Synth Catal

View full text Add to dashboard Cite

show abstract

ChemInform Abstract: Benzazoles. Part 2. Synthesis and Arenesulfonylation of 1‐Methyl‐1H‐benzimidazol‐2‐amine.

et al. 2014

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Benzazoles: III. Synthesis and Transformations of 6-(Chlorosulfonyl)-1,3-benzothiazol-2(3H)-ones

et al. 2020

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Benzazoles: II. Synthesis and arenesulfonylation of 1-methyl-1H-benzimidazol-2-amine

Cited by 3 publications

References 5 publications

Synthesis of Cyclohexenone(aryl)iodonium Salts and Their Application in Construction of Fused aza‐Heterocyclic Skeletons

Synthesis of Cyclohexenone(aryl)iodonium Salts and Their Application in Construction of Fused aza‐Heterocyclic Skeletons

ChemInform Abstract: Benzazoles. Part 2. Synthesis and Arenesulfonylation of 1‐Methyl‐1H‐benzimidazol‐2‐amine.

Benzazoles: III. Synthesis and Transformations of 6-(Chlorosulfonyl)-1,3-benzothiazol-2(3H)-ones

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