18039-45-7Relevant academic research and scientific papers
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 (2002)
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-
One-Pot Suzuki-Hydrogenolysis Protocol for the Modular Synthesis of 2,5-Diaryltetrazoles
Bertrand, Sophie,Jamieson, Craig,Livingstone, Keith
, p. 7413 - 7423 (2020/07/07)
2,5-Diaryltetrazoles are a diverse range of compounds of considerable interest within the field of photochemistry as a valuable precursor of the nitrile imine 1,3-dipole. Current literature approaches toward this heterocycle remain unsuitable for the prac
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.
Phototriggered Active Alkyne Generation from Cyclopropenones with Visible Light-Responsive Photocatalysts
Mishiro, Kenji,Kimura, Takeshi,Furuyama, Taniyuki,Kunishima, Munetaka
supporting information, p. 4101 - 4105 (2019/06/17)
A photocatalytic active alkyne generation reaction was developed using cyclopropenone as a starting reagent. Visible light-responsive photocatalysts induced cyclopropenone decarbonylation. The resulting highly reactive alkyne could be used directly, witho
Application of Photoclick Chemistry for the Synthesis of Pyrazoles via 1,3-Dipolar Cycloaddition between Alkynes and Nitrilimines Generated In Situ
Remy, Richard,Bochet, Christian G.
, p. 316 - 328 (2018/01/27)
The photochemical extrusion of gaseous nitrogen from 2,5-disubstituted tetrazoles to generate reactive nitrilimines in situ represents an efficient and attractive way to form dipoles that can be used to provide useful chemicals via 1,3-dipolar cycloadditions. The concept of “photoclick chemistry” already inspired numerous researchers, who exploited photochemical processes involving alkenes for the synthesis of adducts or the functionalization of biocompatible materials. The approach requires bioorthogonality, ease of access to the starting materials and operational simplicity. We report herein our investigations toward a photoclick reaction involving 2,5-disubstituted tetrazoles and alkynes as the dipolarophile for the synthesis of pyrazole derivatives. In addition to the numerous reports recently published on the synthesis of pyrazoles, we wish to add to the list a photochemical procedure that represents a mild and atom-economical alternative. Moreover, considering that such nitrilimines precursors can be accessed in one step from inexpensive and abundant starting materials and given the commercial availability of a broad spectrum of alkynes, we examined the scope of the photoclick reaction with respect to reactive partners, enabling the synthesis of a library of useful heteroaromatics.
Synthesis method of drug intermediate 2-aryl-substituted tetrazole compound
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Paragraph 0027; 0030; 0031; 0032; 0033; 0034-0037, (2017/08/29)
The invention provides a synthesis method of a 2-aryl-substituted tetrazole compound. The method comprises the following step: in the existence of a catalyst, base and ligand, reacting a tetrazole compound with an aryl compound in oxygen and organic solvents, so as to obtain the 2-aryl-substituted tetrazole compound. The high-yield synthesis of the 2-aryl-substituted tetrazole compound can be realized, and the method has good application prospects and industrial production potential.
One-Pot Reactions for Synthesis of 2,5-Substituted Tetrazoles from Aryldiazonium Salts and Amidines
Ramanathan, Mani,Wang, Yu-Hao,Liu, Shiuh-Tzung
supporting information, p. 5886 - 5889 (2015/12/11)
One-pot sequential reactions of aryldiazonium salts with amidines followed by the treatment of I2/KI under basic conditions provide 2,5-disubstituted tetrazoles in moderate to excellent yields. This one-pot synthesis has several advantages such as mild reaction conditions, short reaction time, convenient workup, and high yields, making this methodology practical.
5-substituted-2-2H-tetrazoleamine manufacturing method
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Paragraph 0030-0031; 0040; 0057-0058, (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.
Regiospecific Synthesis of N 2-Aryl 1,2,3-Triazoles from 2,5-Disubstituted Tetrazoles via Photochemically Generated Nitrile Imine Intermediates
Stewart, Sam,Harris, Robert,Jamieson, Craig
supporting information, p. 2480 - 2484 (2015/07/27)
The synthesis of N2-aryl 1,2,3-triazoles from 2,5-disubstituted tetrazoles was achieved under photochemical conditions. This simple and mild one-step reaction provides regiospecific access to 2,4,5-substituted 1,2,3-triazoles via a nitrile imine intermediate. Syntheses of alkyl and heterocylic derivatives were also investigated.
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.
