- Iron-catalyzed oxidative dehydrogenative coupling of ethers with aryl tetrazoles
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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
- Zhu, Kai-Qiang,Wang, Liang,Chen, Qun,He, Ming-Yang
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- Bu4NI-Catalyzed, Radical-Induced Regioselective N-Alkylations and Arylations of Tetrazoles Using Organic Peroxides/Peresters
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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.
- Ghosh, Subhendu,Mir, Bilal Ahmad,Patel, Bhisma K.,Rajamanickam, Suresh,Sah, Chitranjan,Sethi, Garima,Venkataramani, Sugumar,Yadav, Vinita
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p. 2118 - 2141
(2020/03/13)
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- Alkylation of 5-Substituted Tetrazoles with Various Alcohols in 1,2-Dichloroethane in the Presence of BF3·Et2O
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Abstract: The alkylation of 1H-tetrazole, 5-methyl-1H-tetrazole, and 5-phenyl-1H-tetrazole with primary, secondary, and tertiary alcohols, including benzylic and allylic ones, have been studied in 1,2-dichloroethane in the presence of boron trifluoride–diethyl ether complex. Neither primary nor secondary saturated alcohols alkylated tetrazoles in the given system. Tertiary alcohols such tert-butyl alcohol and adamantan-1-ol reacted with unsubstituted and 5-substituted tetrazoles to give 70–85% of the corresponding 2-alkyl-5-R-tetrazoles with high regioselectivity. The alkylation of 1H-tetrazole with benzyl alcohol afforded 55% of 2-benzyl-2H-tetrazole as the only product. The alkylation of 1H-tetrazole with various allylic alcohols led to the formation of mixtures of 2-alkyl-2H-tetrazoles with isomeric alkyl substituents.
- Egorov, S. A.,Ishchenko, M. A.,Ivanova, V. I.,Prokopovich, Ya. V.
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p. 1196 - 1203
(2020/10/02)
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- Alkylation of 5-substituted NH-tetrazoles by alcohols in the superacid CF3SO3H
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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.
- Lisakova, Anna D.,Ryabukhin, Dmitry S.,Trifonov, Rostislav E.,Ostrovskii, Vladimir A.,Vasilyev, Aleksander V.
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supporting information
p. 7020 - 7023
(2015/11/27)
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- Selective synthesis of 1,3-di- and 1,3,5-trisubstituted tetrazolium salts by tert-butylation of tetrazole, 1- and 5-monosubstituted tetrazoles. Isomerization of 1,3-disubstituted salts to 1,4-salts
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Tetrazole and ils 1 - and 5-monosubstituted derivatives are found to react with tert-butyl alcohol in 72% perchloric acid media, yielding selectively 1,3-di- and 1,3,5-trisubstituted tetrazolium salts. 1.3-Disubstituted salts are slowly converted under th
- Gaponik,Voitekhovich,Maruda,Kulak,Ivashkevich
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p. 2247 - 2253
(2007/10/03)
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- 2-[2-(5-tetrazolyl)phenyl]-1,2-dihydroquinoline derivatives
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A compound of formula (1): STR1 in which R1 represents a 1,1-dimethylethyl, triphenylmethyl, methoxymethyl or benzyloxymethyl group; and R2 represents a C1 -C4 alkyl group.
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- SELECTIVE N(2) ALKYLATION OF TETRAZOLE AND 5-SUBSTITUTED TETRAZOLES BY ALCOHOLS
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Alkylation of tetrazole and its 5-substituted derivatives by tert-butyl, isopropyl, and cyclohexyl alcohols in concentrated H2SO4 results in high yields of the corresponding 2-alkyltetrazoles alone, irrespective of electronic properties and size of the su
- Koren', A. O.,Gaponik, P. N.
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p. 1366 - 1370
(2007/10/02)
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