53918-41-5Relevant academic research and scientific papers
Synthesis of 5-{[(1-Aryl-1H-1,2,3-triazol-4-yl)methyl]sulfanyl}-1-phenyl-1H-tetrazoles
Kedika, B.,Noole, V. G.,Reddy, C. H. Krishna,Thotla, K.
, p. 1077 - 1081 (2020)
Abstract: A series of novel 5-(1,2,3-triazolylmethylsulfanyl)tetrazole derivatives were synthesized by the click reaction from 1-phenyl-5-(prop-2-yn-1-ylsulfanyl)-1H-tetrazole and the corresponding azide. The reaction optimization results showed that higher yields are obtained using CuSO4 and sodium ascorbate in DMF–water (2:1). The product structures were established on the basis of various spectral data, and their evaluation for antimicrobial activity showed moderate to good results compared to standard drugs.
Photochemical Doyle-Kirmse Reaction: A Route to Allenes
Or?owska, Katarzyna,Rybicka-Jasińska, Katarzyna,Krajewski, Piotr,Gryko, Dorota
supporting information, p. 1018 - 1021 (2020/01/31)
This Letter describes the metal-free, blue-light-induced [2,3]-sigmatropic rearrangement of sulfonium ylides generated from donor/acceptor diazoalkanes and propargyl sulfides. The reaction furnishes highly functionalized allenes from a broad range of starting materials in decent yield. Mechanistic experiments supported by the literature data suggest singlet carbenes as intermediates in this reaction.
Alkylation of thiols with trichloroacetimidates under neutral conditions
Duffy, Brian C.,Howard, Kyle T.,Chisholm, John D.
supporting information, p. 3301 - 3305 (2015/03/04)
Trichloroacetimidates are displaced with thiols to form the corresponding sulfides without the need for an added acid or base by simply heating the reactants in refluxing THF. This operationally simple procedure provides the corresponding sulfides in excellent yields with only the formation of the neutral trichloroacetamide as the side product. The imidate may also be formed in situ, allowing for a direct method for the formation of sulfides from alcohols. This reaction provides a general method for the synthesis of a variety of sulfides from inexpensive and readily available alcohol starting materials.
Nonsymmetrical azocarbonamide carboxylates as effective Mitsunobu reagents
Furkert, Daniel P.,Breitenbach, Benjamin,Juen, Ludovic,Sroka, Ina,Pantin, Mathilde,Brimble, Margaret A.
supporting information, p. 7806 - 7809 (2015/02/02)
A family of nonsymmetrical Mitsunobu reagents possessing both dialkyl amide and ester substituents was developed. These new reagents were readily prepared in a single pot from inexpensive, commercially available materials by using a scalable and environmentally friendly procedure. They were shown to exhibit activity parallel to that of diethyl azodicarboxylate/diisopropyl azodicarboxylate in a wide variety of Mitsunobu reactions. Importantly, the acyl hydrazine reaction byproducts were readily separable from the crude mixture by standard aqueous workup. In addition, the discovery of effective nonsymmetrical Mitsunobu reagents offers new directions for the ongoing development of this important reaction.
A convenient preparation of di-p-chlorobenzyl azodicarboxylate (DCAD) for mitsunobu couplings
Taft, Benjamin R.,Swift, Elizabeth C.,Lipshutz, Bruce H.
scheme or table, p. 332 - 334 (2009/06/18)
Gram-scale synthesis of pure, bench-stable solid di-p-chlorobenzyl azodicarboxylate (DCAD) is performed in two steps without resorting to chromatography. This novel reagent effects Mitsunobu couplings with yields comparable to DEAD or DIAD, while addressi
Simplification of the Mitsunobu reaction. Di-p-chlorobenzyl azodicarboxylate: A new azodicarboxylate
Lipshutz, Bruce H.,Chung, David W.,Rich, Brian,Corral, Ricardo
, p. 5069 - 5072 (2007/10/03)
(Chemical Equation Presented) Di-p-chlorobenzyl azodicarboxylate (DCAD) is introduced as a novel, stable, solid alternative to DEAD and DIAD for a variety of Mitsunobu couplings. DCAD/Ph3P-mediated reactions in CH 2Cl2 gen
SINGLE-STEP PREPARATION OF ALLYLIC SULFIDES HAVING 1-PHENYLTETRAZOLE-5-THIO GROUP FROM ALLYLIC ALCOHOLS USING S,S'-BIS(1-PHENYL-1H-TETRAZOL-5-YL) DITHIOCARBONATE AND REACTIONS INVOLVING THE ALLYLIC SULFIDES
Takeda, Kazuyoshi,Tsuboyama, Kanoko,Torii, Katsumi,Murata, Maki,Ogura, Haruo
, p. 4105 - 4108 (2007/10/02)
The reaction of allylic alcohols and S,S'-bis(1-phenyl-1H-tetrazol-5-yl) dithiocarbonate (1) gave allylic sulfides having 1-phenyltetrazole-5-thio group in a single step.Furthermore, these allylic sulfides could be applied to carbon-carbon bond and carbon-sulfur bond formations by using Grignard reagents or carbanions in the presence of catalytic amount of copper(I) bromide or palladium (0), respectively.
