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

Tetrahedron 2012
Māris Turks, Inta Strakova, Kirils Gorovojs, Sergejs Beļakovs, Yuri Piven, Tatyana Khlebnicova, Fedor Lakhvich

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.

Atslēgas vārdi
Tetrahydroindazoles, Ritter reaction, Amides, Nitriles
DOI
10.1016/j.tet.2012.05.074
Hipersaite
http://www.sciencedirect.com/science/article/pii/S0040402012007922

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, 6131.-6140.lpp. ISSN 0040-4020. Pieejams: doi:10.1016/j.tet.2012.05.074

Publikācijas valoda
English (en)