Efficient synthesis of N-arylsulfonyl-1,2,3-triazoles from 1,1-dibromo-2-arylethylenes
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.
Citations
More filters
6 citations
TL;DR: In this paper, Dibromoalkenes, prepared from aldehydes under Corey-Fuchs conditions, undergo a tandem process in one pot to give the desired alkyne products within a short time.
Abstract: Dibromoalkenes, prepared from aldehydes under Corey—Fuchs conditions, undergo a tandem process in one pot to give the desired alkyne products within a short time.
2 citations
01 Jan 2011
TL;DR: NH-1,2,3-triazoles are a kind of N-containing heterocylic compounds with important biological activities, which have found broad use in medicinal intermediates as mentioned in this paper.
Abstract: NH-1,2,3-Triazoles are a kind of N-containing heterocylic compounds with important biological activities, which have found broad use in medicinal intermediates. Besides, NH-1,2,3-triazoles serve as valuable synthetic intermediates for the preparation of 2-substituded-1,2,3-triazoles through N-alkylation re- action. Because of their potent applications in both synthetic organic chemistry and medicinal chemistry, the progess in the synthesis of NH-1,2,3-triazoles, especially those reported in the past decade, is surveyed ac- cording to the research by our group and other groups. Some classical reaction mechanics are also reviewed in this paper.
1 citations
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.
12 Apr 2013
TL;DR: Microwave assisted tandem reaction of (Z )-arylvinyl bromides involving an elimination and homocoupling in the presence of DBU and CuI in DMF affords a variety of symmetrical 1,3-diynes in good to excellent yields.
Abstract: Microwave-assisted tandem reaction of ( Z )-arylvinyl bromides involving an elimination and homocoupling in the presence of DBU and CuI in DMF affords a variety of symmetrical 1,3-diynes in good to excellent yields. This tandem process, eliminating the need of volatile and savory terminal alkynes, provides an alternative to the conventional homocoupling methods for the synthesis of symmetrical 1,3-diynes.
References
More filters
10,370 citations
TL;DR: The copper-catalyzed cycloaddition reaction between azides and alkynes functions efficiently in aqueous solution in the presence of a tris(triazolyl)amine ligand to make rapid and reliable covalent connections to micromolar concentrations of protein decorated with either of the reactive moieties.
Abstract: The copper-catalyzed cycloaddition reaction between azides and alkynes functions efficiently in aqueous solution in the presence of a tris(triazolyl)amine ligand. The process has been employed to make rapid and reliable covalent connections to micromolar concentrations of protein decorated with either of the reactive moieties. The chelating ligand plays a crucial role in stabilizing the Cu(I) oxidation state and protecting the protein from Cu(triazole)-induced denaturation. Because the azide and alkyne groups themselves are unreactive with protein residues or other biomolecules, their ligation is of potential utility as a general bioconjugation method.
1,602 citations
1,231 citations
TL;DR: Stable and readily available 1-sulfonyl triazoles are converted to the corresponding imidazoles in good to excellent yields via a rhodium(II)-catalyzed reaction with nitriles.
Abstract: Stable and readily available 1-sulfonyl triazoles are converted to the corresponding imidazoles in good to excellent yields via a rhodium(II)-catalyzed reaction with nitriles. Rhodium iminocarbenoids are proposed intermediates.
406 citations
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