59772-96-2Relevant articles and documents
Iron-catalyzed oxidative dehydrogenative coupling of ethers with aryl tetrazoles
Zhu, Kai-Qiang,Wang, Liang,Chen, Qun,He, Ming-Yang
, p. 4943 - 4946 (2015)
Abstract An iron-catalyzed oxidative dehydrogenative coupling of ethers with aryl tetrazoles has been developed. A wide variety of tetrazoles and ethers survived the reaction conditions to deliver the corresponding hemiaminal derivatives in moderate to go
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.
Alkylation of 5-substituted NH-tetrazoles by alcohols in the superacid CF3SO3H
Lisakova, Anna D.,Ryabukhin, Dmitry S.,Trifonov, Rostislav E.,Ostrovskii, Vladimir A.,Vasilyev, Aleksander V.
supporting information, p. 7020 - 7023 (2015/11/27)
Reactions of 5-substituted NH-tetrazoles with alcohols in the superacid CF3SO3H have been studied. Both the structure of the tetrazole and the nature of alcohol were found to dramatically influence the selectivity of the reaction and yields of products. Tetrazoles bearing phenyl, electron-donating aryl, or benzyl groups at the 5-position, have been alkylated using various alcohols (including MeOH and EtOH) in CF3SO3H upon heating at 60 °C for 0.3-12 h to afford 2-alkyl-2H-tetrazoles in 30-98% yields.