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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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Book ChapterDOI
TL;DR: The interesting finding for the present chapter is that the NO is formed by nitric oxide synthetase from arginine—the only essential amino acid which carries a guanidine group.
Abstract: Publisher Summary This chapter focuses on amidines and guanidines in medicinal chemistry. The drugs are classified under their main physiological activities and within each group are arranged roughly in order of increasing molecular complexity. Many of the compounds have given temporary excitement to their discoverers and then been dropped—the commonest experience in medicinal chemistry. There are important, clinically used, medicines in all the major categories of therapeutic action discussed in the chapter. This simple and very unstable compound is not only a neurotransmitter in the brain, but acts in the dilation of blood vessels and activates leucocytes to attack tumour cells, fungi, and bacteria. In addition, nitric oxide can inhibit blood coagulation by preventing platelet aggregation and appears to be the regulator of the male erection. No doubt other functions will be discovered in the future, but the interesting finding for the present chapter is that the NO is formed by nitric oxide synthetase from arginine—the only essential amino acid which carries a guanidine group. Since most of the active guanidine drugs have at least one unsubstituted =NH or NH 2 group, it is interesting to speculate that they will be shown to act by giving nitric oxide as well.

202 citations

Journal ArticleDOI
TL;DR: Microwave reactions of primary and secondary amines with imidoylbenzotriazoles 6a-w gave diversely substituted amidines 7a-Aa in 76-94% yields, demonstrating further the advantages of microwave synthesis and introducing a new application of imidoyslbenZotrizoles in the preparation of polysubstituted amidines.
Abstract: Microwave reactions of primary and secondary amines with imidoylbenzotriazoles 6a−w gave diversely substituted amidines 7a−Aa in 76−94% yields. Convenient preparations of a variety of amides 5a−Ab (87−96%) and imidoylbenzotriazoles 6a−w (56−95%) have also been developed using microwave irradiation under mild conditions and short reaction times. These results demonstrate further the advantages of microwave synthesis and introduce a new application of imidoylbenzotriazoles in the preparation of polysubstituted amidines.

103 citations

Journal ArticleDOI
Weijun Yao1, Lianjie Pan1, Yiping Zhang1, Gang Wang1, Xiaoqin Wang1, Cheng Ma1 
TL;DR: A novel copper(I)-catalyzed three-component reaction (3-CR) is presented to produce functionalized N-sulfonyl-2-iminooxetanes 5 by a [2 + 2] cycloaddition of aromatic 2-oxobut-3-ynoates 2 with N-SulfonyLketenimines I generated in situ.
Abstract: Reactions of α-keto esters with N-sulfonylketimines, prepared in situ from terminal alkynes and azide (III), proceeds via 2-iminooxetane intermediates such as (VII) which are transformed into maleimide derivatives or 5-iminopyrrolidinones.

80 citations

Journal ArticleDOI
TL;DR: In this paper, the double insertion of the isothiocyanate was used to achieve a mechanistically novel reaction to afford highly substituted dialkyl 2-(benzoylimino)-5-phenyl-4H-[1,3]dithiolo[4,5-b]pyrrole-4,6-dicarboxylates.

23 citations

Frequently Asked Questions (1)
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.