Synthesis of 1-(adamantan-1-yl)-1H-1,2,3-triazoles and their salts by adamantylation in AdOH-HClO4 and AdOH-H2SO4 systems

Synthesis of 1-(adamantan-1-yl)-1H-1,2,3-triazoles and their salts by adamantylation in AdOH-HClO4 and AdOH-H2SO4 systems Full article

Journal

Chemistry of Heterocyclic Compounds
ISSN: 0009-3122 , E-ISSN: 1573-8353

Output data

Year: 2019, Volume: 55, Number: 12, Pages: 1197-1203 Pages count : 7 DOI: 10.1007/s10593-019-02601-7

Tags

adamantan-1-ol; 1-(adamantan-1-yl)-3-alkyl-1,2,3-triazolium salt; 1-(adamantan-1-yl)-1H-1,2,3-triazole; alkyl sulfate; perchloric acid; sulfuric acid; 1,2,3-triazole; adamantylation; quaternization; regioselectivity

Authors

Sukhanov Gennady T. ¹ , Filippova Yuliya V. ¹ , Sukhanova Anna G. ¹ , Bagryanskaya Irina Yu. ^2,3 , Bosov Konstantin K. ¹

Affiliations

1	Institute for Problems of Chemical and Energy Technologies, Siberian Branch of the Russian Academy of Sciences, 1 Sotsialisticheskaya St., Biysk 659322, Russia
2	N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 Akademika Lavrentieva Ave., Novosibirsk 630090, Russia
3	Novosibirsk State University, 2 Pirogova St., Novosibirsk 630090, Russia

1-(Adamantan-1-yl)-1H-1,2,3-triazoles and a series of 1-(adamantan-1-yl)-3-alkyl-1,2,3-triazolium salts were synthesized by regioselective adamantylation of 1,2,3-triazole derivatives. The direction of the attack by the adamantyl cation at the N-1 nitrogen atom and the regioselectivity of the processes of adamantylation and quaternization are ensured by a number of factors: the specificity of the properties of the high-acid systems AdOH-HClO4 and AdOH-H2SO4, as well as the structural aspect and high reactivity of adamantan-1-ol.

Sukhanov G.T. , Filippova Y.V. , Sukhanova A.G. , Bagryanskaya I.Y. , Bosov K.K.
Synthesis of 1-(adamantan-1-yl)-1H-1,2,3-triazoles and their salts by adamantylation in AdOH-HClO4 and AdOH-H2SO4 systems
Chemistry of Heterocyclic Compounds. 2019. V.55. N12. P.1197-1203. DOI: 10.1007/s10593-019-02601-7 WOS Scopus РИНЦ

Суханов Г.T. , Филиппова Ю.В. , Суханова А.Г. , Багрянская И.Ю. , Босов К.К.
Cинтез 1-(адамантан-1-ил)-1H-1,2,3-триазолов и их солей адамантилированием в системах AdOH–HClO4 и AdOH–H2SO4
Химия гетероциклических соединений/Khimiya Geterotsiklicheskikh Soedinenii. 2019. Т.55. №12. С.1197-1203.

Submitted:	Jun 26, 2019
Accepted:	Sep 22, 2019
Published print:	Dec 1, 2019
Published online:	Dec 24, 2019

Web of science	WOS:000510838400009
Scopus	2-s2.0-85077142921
Elibrary	43225198
OpenAlex	W2998316633