20433-11-8Relevant academic research and scientific papers
Bu4NI-Catalyzed, Radical-Induced Regioselective N-Alkylations and Arylations of Tetrazoles Using Organic Peroxides/Peresters
Ghosh, Subhendu,Mir, Bilal Ahmad,Patel, Bhisma K.,Rajamanickam, Suresh,Sah, Chitranjan,Sethi, Garima,Venkataramani, Sugumar,Yadav, Vinita
, p. 2118 - 2141 (2020/03/13)
Bu4NI-catalyzed regioselective N2-methylation, N2-Alkylation, and N2-Arylation of tetrazoles have been achieved using tert-butyl hydroperoxide (TBHP) as the methyl source, alkyl diacyl peroxides as the primary alkyl source, alkyl peresters as the secondary and tertiary alkyl sources, and aryl diacyl peroxides as the arylating source. These reactions proceed without pre-functionalization of tetrazole and in the absence of any metal catalysts. Here, peroxides serve the dual role of oxidants as well as alkylating or arylating agents. Based on DFT calculations, it was found that spin density, transition-state barriers (kinetic control), and thermodynamic stability of the products (thermodynamic control) play essential roles in the observed regioselectivity during N-Alkylation. This radical-mediated process is amenable to a broad range of substrates and provides products in moderate to good yields.
5-substituted-2-2H-tetrazoleamine manufacturing method
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Paragraph 0030-0032; 0040, (2021/09/18)
The present invention is a method for producing a 5-substituted-2-aryl-2H-tetrazole that is useful as an intermediate for producing a pharmaceutical compound, and relates to a method which selectively introduces an aryl group in the 2 position.
Cu(OH)(TMEDA)2Cl2-catalyzed regioselective 2-arylation of 5-substituted tetrazoles with boronic acids under mild conditions
Onaka, Takuya,Umemoto, Hideaki,Miki, Yasuyoshi,Nakamura, Akira,Maegawa, Tomohiro
, p. 6703 - 6707 (2014/08/05)
A mild and regioselective 2-arylation of 5-substituted tetrazoles is described. The reaction proceeds regioselectively with a variety of arylboronic acids in the presence of [Cu(OH)(TMEDA)]2Cl2 to afford 2,5-disubstituted tetrazoles. This is the first report of highly regioselective arylation of 5-alkyltetrazoles.
Palladium- and copper-catalyzed selective arylation of 5-aryltetrazoles by diaryliodonium salts
Beletskaya, Irina P.,Davydov, Dmitri V.,Gorovoy, Matvey S.
, p. 6221 - 6223 (2007/10/03)
Palladium(0)-catalyzed arylation of 5-aryltetrazoles in t-BuOH at 80°C with diaryliodonium salts proceeds in the presence of copper(II) phenylcyclopropyl carboxylate regioselectively at the N2 position.
Regioselective arylation of N-tributylstannylated 5-substituted tetrazoles by diaryliodonium salts in the presence of Cu(OAc)2
Davydov, Dmitri V.,Beletskaya, Irina P.,Semenov, Boris B.,Smushkevich, Yuri I.
, p. 6217 - 6219 (2007/10/03)
The arylation of N-tributylstannylated 5-substituted tetrazoles with diaryliodonium salts at room temperature without base in CH2Cl2 in the presence of stoichiometric amounts of Cu(OAc)2 proceeds regioselectively at the N-
Synthesis of Some Triazole, Tetrazole, and Tetrazine Derivatives from N-β-Naphthalenesulfonylbenzohydrazidoyl Chlorides
Hassaneen, Hamdi M.,Fahmi, Abdelgawad A.,Abdelhamid, Hyam,Yassin, Ahmady A.,Shawali, Ahmad S.
, p. 797 - 800 (2007/10/02)
A series of N-β-naphthalenesulfonylbenzohydrazidoyl chlorides 8a-d has been prepared by the action of thionyl chloride on the corresponding hydrazides 7a-d.Treatment of 8 with triethylamine and morpholine afforded the tetrazines 10 and the amidrazones 11 respectively.Acid hydrolysis of 11 yielded the hydrazides 7.Reaction of 8 with phenylhydrazine gave 3,5-diaryltetrazoles 14.However, reaction of 8 with aroylhydrazines yielded 3,5-diaryl-4-β-naphthalenesulfonylamino-4H-1,2,4-triazoles 15.The structures of the products were assigned upon the basis of their spectra, elemental analyses and alternative synthesis whereever possible.
