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Journal ArticleDOI

Synthesis of Functionalized N-Sulfonylamidines from N-Sulfonylketenimines and 2-Aminobenzimidazole

06 Mar 2015-Synthetic Communications (Taylor & Francis)-Vol. 45, Iss: 9, pp 1089-1093
TL;DR: In this paper, the synthesis of a novel class of N-(1H-benzo[d]imidazol-2-yl)-2-alkyl-N′-sulfonylacetamidines via a copper-catalyzed, three-component coupling reaction of 1H-benezol 2-amine, sulfonyl azides, and terminal alkynes is described.
About: This article is published in Synthetic Communications.The article was published on 2015-03-06 and is currently open access. It has received 4 citations till now. The article focuses on the topics: Tosyl azide & Sulfonyl.

Summary (1 min read)

General Procedure for the Preparation of Compounds 5

  • The mixture was stirred at room temperature.
  • The residue was purified by flash column chromatography Merck) , AcOEt/hexane 1:3] to give product.

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Citations
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Journal ArticleDOI
TL;DR: In this article, N-arylsulfonyl-1,2,3-triazoles were synthesized from 1,1-dibromo-2-arylethylenes via a one-pot reaction involving the Cs2CO3-mediated dehydrobromination process of the dibromoealkenes to produce alkynes followed by the Cu(I)-catalyzed Huisgen cycloaddition of the alkyne intermediates with tosyl azide.
Abstract: Abstract N-arylsulfonyl-1,2,3-triazoles were synthesized from 1,1-dibromo-2-arylethylenes via a one-pot reaction involving the Cs2CO3-mediated dehydrobromination process of the dibromoalkenes to produce alkynes followed by the Cu(I)-catalyzed Huisgen cycloaddition of the alkyne intermediates with tosyl azide.

5 citations

Journal ArticleDOI
TL;DR: In this article, an efficient synthesis of 1-arylsulfonyl-1,2,3-triazoles from easily available (Z)-arylvinyl bromides is described.
Abstract: Efficient synthesis of 1-arylsulfonyl-1,2,3-triazoles from easily available (Z)-arylvinyl bromides is described. The sequential reaction involves elimination of HBr from (Z)-arylvinyl bromides promoted by KOH and copper-catalyzed (3+2) cycloaddition reaction between the alkyne intermediates and sulfonyl azides.

4 citations

Book ChapterDOI
01 Jan 2022
TL;DR: In this paper , the synthesis and use of N-sulfonyl triazole and tetrazole is discussed and their applications in medicine and pharmaceuticals are discussed. But the main focus of this paper is on the synthesis of tetrazoles.
Abstract: N-sulfonyl triazole is an intermediate in organic synthesis and has been proven to be an excellent nitrogen source for the construction of many heterocycles. Due to its more favorable pharmacokinetic properties, tetrazole has also been proven to be a suitable bioisostere derived from a carboxylic acid and cisamide units. This chapter summarizes the new and innovative synthetic strategies that have been developed for the synthesis and ring-opening of N-sulfonyl triazoles and tetrazoles. This chapter covers the chemistry of N-sulfonyl triazole and tetrazole and their applications in medicine and pharmaceuticals. Initially, we discussed various synthetic methods of N-sulfonyl-1,2,3-triazoles, and then how reactive N-sulfonyltriazole is sufficient to open the ring and form acyclic amine derivatives (β-phenethylamine, o-diamine, allylamine, enamine, and Ketimine) or other cyclic N-sulfonylamines. This chapter also introduces the synthesis and use of N-sulfonyl-1,2,3,4-tetrazole. We focused on the synthetic development for the production of N-sulfonyl triazole and tetrazole and their reaction types.
Journal ArticleDOI
TL;DR: In this article, the synthesis of a novel class of N-(1H-benzo[d]imidazol-2-yl)-2-alkyl-N′-sulfonylacetamidines via a copper-catalyzed, three-component coupling reaction of 1H-benezol 2-amine, sulfonyl azides, and terminal alkynes is described.
Abstract: The synthesis of a novel class of N-(1H-benzo[d]imidazol-2-yl)-2-alkyl-N′-sulfonylacetamidines via a copper-catalyzed, three-component coupling reaction of 1H-benzo[d]imidazol-2-amine, sulfonyl azides, and terminal alkynes is described.
References
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Journal ArticleDOI
TL;DR: In this article, a review of metal-metal bridging with the presence of the amidino group is presented, with a focus on bridging modes for the group and a reference to other aza-allyl systems.

631 citations

Journal ArticleDOI
Imhyuck Bae1, Hoon Han1, Sukbok Chang1
TL;DR: Two plausible mechanistic pathways involving ketenimine or triazole intermediate are tentatively presented for the copper-catalyzed three-component coupling reactions.
Abstract: A highly efficient, mild, practical, and catalytic multicomponent reaction for the synthesis of N-sulfonylamidines has been developed. This reaction has an extremely wide scope with regard to all three coupling components of alkyne, sulfonyl azide, and amine. Two plausible mechanistic pathways involving ketenimine or triazole intermediate are tentatively presented for the copper-catalyzed three-component coupling reactions.

384 citations

Journal ArticleDOI
TL;DR: 4-Substituted 1-(N-sulfonyl)-1,2,3-triazoles are selectively obtained by using the Cu-catalyzed azide-alkyne cycloaddition reaction with sulfonyl azides and provides convenient access to N-Sulfonyltriazoles in good to excellent yields.
Abstract: (Chemical Equation Presented) 4-Substituted 1-(N-sulfonyl)-1,2,3-triazoles are selectively obtained by using the Cu-catalyzed azide-alkyne cycloaddition reaction with sulfonyl azides. Performing the reaction at 0°C in chloroform in the presence of 2,6-lutidine and Cul as the catalyst effectively prevents the ketenimine pathway and provides convenient access to N-sulfonyltriazoles in good to excellent yields.

280 citations

Journal ArticleDOI
TL;DR: The review of several practical and versatile approaches to ketenimine chemistry and the discovery of a variety of highly efficient reactions are presented here.
Abstract: Ketenimines are an important class of reactive species and useful synthetic intermediates. During the last two decades several practical and versatile approaches to ketenimines have been developed, leading to exhaustive investigations on ketenimine chemistry and the discovery of a variety of highly efficient reactions. Five types of reactions for ketenimines have been reported, including nucleophilic additions (ketenimines can be used as both electrophiles and nucleophiles), radical additions, cycloaddition reactions, electrocyclic ring closure reactions, and σ rearrangements. Furthermore, numerous complex organic compounds, particularly the biologically interesting heterocycles, have been constructed using these methodologies. The review of these accomplishments is presented here.

207 citations

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Q1. What have the authors contributed in "Synthesis of functionalized n-sulfonylamidines from n-sulfonylketenimines and 2-aminobenzimidazole" ?

In this paper, the synthesis of a novel class of N- ( 1H-benzo [ d ] imidazol-2-yl ) -2-alkyl-N'sulfonylacetamidines via a copper-catalyzed three-component coupling reaction of 1Hbenzo [ d ] IMIDazol 2-amine, sulfonyl azides and terminal alkynes is described.