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Publikācija: A Facile Synthesis of 4-Acylamino-Tetrahydroindazoles via the Ritter Reaction

Publication Type Publication (anonimusly reviewed) in a journal with an international editorial board indexed in other databases
Funding for basic activity Unknown
Defending: ,
Publication language English (en)
Title in original language A Facile Synthesis of 4-Acylamino-Tetrahydroindazoles via the Ritter Reaction
Field of research 1. Natural sciences
Sub-field of research 1.4 Chemical sciences
Authors Māris Turks
Inta Strakova
Kirils Gorovojs
Sergejs Beļakovs
Yuri Piven
Tatyana Khlebnicova
Fedor Lakhvich
Keywords Tetrahydroindazoles, Ritter reaction, Amides, Nitriles
Abstract A new route toward 4-acylamino- and 4-amino-substituted tetrahydroindazoles is disclosed. The title compounds are obtained in good to excellent yields in the Ritter reaction between 4-hydroxy-tetrahydroindazoles and various nitriles. The reactivity of the tetrahydroindazole-derived carbenium ion is both sufficiently high to react with trichloroacetonitrile and sufficiently selective to resist the azide functionality within its structure. The present approach adds a method to the toolbox of tetrahydroindazole chemistry and facilitates the structural modifications of the scaffold, which has found important applications in medicinal chemistry.
DOI: 10.1016/j.tet.2012.05.074
Hyperlink: http://www.sciencedirect.com/science/article/pii/S0040402012007922 
Reference Turks, M., Strakova, I., Gorovojs, K., Beļakovs, S., Piven, Y., Khlebnicova, T., Lakhvich, F. A Facile Synthesis of 4-Acylamino-Tetrahydroindazoles via the Ritter Reaction. Tetrahedron, 2012, Vol.68, Iss.31, pp.6131-6140. ISSN 0040-4020. Available from: doi:10.1016/j.tet.2012.05.074
ID 13528