77455-51-7Relevant 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.
Preparation of 5-Aryl-2-Alkyltetrazoles with Aromatic Aldehydes, Alkylhydrazine, Di-tert-butyl Azodicarboxylate, and [Bis(trifluoroacetoxy)iodo]benzene
Imai, Taro,Harigae, Ryo,Moriyama, Katsuhiko,Togo, Hideo
, p. 3975 - 3980 (2016/05/24)
A variety of 5-aryl-2-methyltetrazoles and 5-aryl-2-benzyltetrazoles were directly prepared in good to moderate yields by the reaction of aromatic aldehydes with methylhydrazine and benzylhydrazine, followed by treatment with di-tert-butyl azodicarboxylate and [bis(trifluoroacetoxy)iodo]benzene in a mixture of dichloromethane and 2,2,2-trifluoroethanol at room temperature. The present method is a novel one-pot preparation of 5-aryl-2-methyltetrazoles and 5-aryl-2-benzyltetrazoles through a [2N + 2N] combination under transition metal-free and mild conditions.
An Environmentally Friendly Method for N-Methylation of 5-Substituted 1H-Tetrazoles with a Green Methylating Reagent: Dimethyl Carbonate
Xie, Aming,Zhang, Qiang,Liu, Yangyang,Feng, Liandong,Hu, Xinyu,Dong, Wei
, p. 1483 - 1487 (2015/10/06)
An environmentally friendly method was established for the N-methylation of the 5-substituted 1H-tetrazoles with a green reagent: DMC. DABCO was the optimal catalyst, and hazardous chemicals were avoided in this protocol. A plausible catalytic mechanism is proposed, which consists of a DABCO-activated process and a thermally induced rearrangement of tetrazole carbamates.
Rhodium-catalyzed olefination of aryl tetrazoles via direct C-H bond activation
Wang, Liang,Wu, Wenting,Chen, Qun,He, Mingyang
, p. 7923 - 7926 (2015/01/09)
Rh(III)-catalyzed direct olefination reaction via aromatic C-H bond activation is described using tetrazole as the directing group. This reaction provides a straightforward way for the synthesis of ortho-alkenyl aryl tetrazoles. Various functional groups tolerate the reaction conditions and afford the corresponding products in moderate to excellent yields.
A Study of Annular Tautomerism, Interannular Conjugation, and Methylation Reactions of ortho-Substituted-5-aryltetrazoles using Carbon-13 and Hydrogen-1 N.M.R. Spectroscopy
Butler, Richard N.,Garvin, Victor C.
, p. 390 - 393 (2007/10/02)
In ortho-substituted-5-phenyltetrazoles, Ar-CN4H (Ar = 2'-MeC6H4, 2'-ClC6H4, or 2',6'-Cl2C6H3), the rings are twisted out of the planar configuration and interannular conjugation is inhibited.In each case the tetrazole 1-NH tautomer is strongly predominan
