127866-65-3Relevant academic research and scientific papers
A note on the antitubercular activities of 1-aryl-5- benzylsulfanyltetrazoles
Adamec, Jan,Waisser, Karel,Kunes, Jiri,Kaustova, Jarmila
, p. 385 - 389 (2005)
A set of 32 1-phenyl-5-benzylsulfanyltetrazoles substituted on the phenyl ring as well as on the benzyl moiety was synthesized. The compounds were evaluated for in vitro antimycobacterial activity against Mycobacterium tuberculosis. The activity against M. tuberculosis becomes higher with increasing electron-accepting properties of the substituents on the phenyl ring. On the other hand, any substitution on the benzylic moiety decreases the activity.
The influence of α-coordinating groups of aldehydes on E/Z-selectivity and the use of quaternary ammonium counter ions for enhanced E-selectivity in the Julia–Kocienski reaction
Rehman, Mintu,Surendran, Sravya,Siddavatam, Nagendra,Rajendar, Goreti
supporting information, p. 329 - 333 (2022/01/20)
Modified reaction conditions for improved E-selectivity of olefins in the Julia–Kocienski reaction of aldehydes having α-coordinating substituents are demonstrated. The chelating groups in aldehydes are expected to stabilize the syn-transition state with metal ions, whereas the weakly coordinating quaternary ammonium ions are devoid of all possible chelating interactions to enhance E-selectivity. A systematic investigation is presented to study the size of the neighbouring protecting groups of aldehydes and their chelation effect on E/Z-selectivity in the Julia–Kocienski reaction.
One-pot preparation of Julia-Kocienski sulfides and sulfones from alcohols
Ando, Kaori,Hattori, Junichiro
, (2019/08/12)
A method for one-pot preparation of Julia-Kocienski sulfides and sulfones from alcohols and thiols is reported. A variety of primary alcohols were converted to the corresponding mesylates by methansulfonyl chloride and triethylamine in THF. After the reaction is complete, thiol (1 or 10) and either NaH or t-BuOK were added. The Julia-Kocienski sulfides 3, 9 and 11 were prepared by one-pot two steps procedure from alcohols in 76–96% yields (16 examples). Furthermore, after the sulfide formation, the reaction mixture was neutralized by p-toluenesulfonic acid and treated with H2O2 and ammonium molybdate in EtOH to give the Julia-Kocienski sulfones 4 in good yields except for trans-2-hexen-1-ol.
Direct Synthesis of Thioethers from Carboxylates and Thiols Catalyzed by FeCl3
Venkatesham, Kunuru,Bhujanga Rao, Chitturi,Dokuburra, Chanti Babu,Bunce, Richard A.,Venkateswarlu, Yenamandra
, p. 11611 - 11617 (2015/12/01)
A new and efficient method has been developed for the synthesis of thioethers from carboxylates and thiols. The reaction proceeds via a Fe(III)-catalyzed direct displacement of carboxylates from benzylic or allylic esters by heterocyclic thiols. Short rea
Ga(OTf)3-catalyzed direct substitution of alcohols with sulfur nucleophiles
Han, Xinping,Wu, Jimmy
supporting information; experimental part, p. 5780 - 5782 (2011/03/18)
It is reported that Ga(OTf)3 catalyzes the direct displacement of alcohols with sulfur nucleophiles. The products are versatile intermediates that can be utilized in carbon - carbon, carbon - sulfur bond formation or used in modified Julia olef
A mild method for the protection of alcohols using a para-methoxybenzylthio tetrazole (PMB-ST) under dual acid-base activation
Kotturi, Santosh R.,Tan, Jason S.,Lear, Martin J.
supporting information; experimental part, p. 5267 - 5269 (2009/12/24)
With a view to expand the repertoire of chemoselective methods applicable to sensitive and multifunctional substrates, the p-methoxybenzylation of alcohols under essentially neutral conditions is reported. This was achieved by the silver triflate (AgOTf) activation of 5-(p-methoxybenzylthio)-1-phenyl-1H-tetrazole (PMB-ST) in the presence of 2,6-di-tert-butyl-4-methylpyridine (DTBMP).
Cytostatic tetrazole-butenolide conjugates: Linking tetrazole and butenolide rings via stille coupling and biological activity of the target substances
Balsanek, Vojtech,Tichotova, Lucie,Kunes, Jiri,Spulak, Marcel,Pour, Milan,Votruba, Ivan,Buchta, Vladimir
experimental part, p. 1161 - 1178 (2010/04/28)
A series of tetrazoles linked to the butenolide core via benzene rings were prepared by the Stille coupling reaction of α-(tributylstannyl) butenolides and 5-(alkylsulfanyl)-1-(4-iodophenyl)tetrazoles, and the compounds were tested for antifungal and cytostatic activity. Interesting antifungal activities against the filamentous strain Absidia corymbifera, and cytostatic activities against leukemic cells HL-60 and CCRF-CEM were found. The cytostatic activity requires the presence of both the butenolide ring and the alkylsulfanyl group bound to tetrazole ring. In addition, the feasibility of Pd-coupling reactions with 5-iodotetrazoles was evaluated.
Total synthesis of artochamins F, H, I, and J through cascade reactions
Nicolaou,Lister, Troy,Denton, Ross M.,Gelin, Christine F.
, p. 4736 - 4757 (2008/09/21)
A concise and efficient cascade-based total synthesis of artochamins F, H, I, and J is described. The potential biogenetic connection between artochamin F, or a derivative thereof, and artochamins H, I, and J, through an unusual formal [2+2] cycloaddition
