M. M. Vinogradov, D. V. Vorobyeva, Yu. V. Nelyubina, S. N. Osipov, D. A. Loginov, “Unusual multiple insertion of diazo carbonyl compounds into (purin-6-yl)benzene derivative”, Mendeleev Commun., 2020, Volume 30, Issue 4,Pages <nobr>494

This article is cited in 3 papers

Communications

Unusual multiple insertion of diazo carbonyl compounds into (purin-6-yl)benzene derivative

M. M. Vinogradov^a, D. V. Vorobyeva^a, Yu. V. Nelyubina^a, S. N. Osipov^ab, D. A. Loginov^ac

^a A.N. Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences, Moscow, Russian Federation
^b Moscow Region State Pedagogical University, Mytishi, Moscow Region, Russian Federation
^c G.V. Plekhanov Russian University of Economics, Moscow, Russian Federation

Abstract: The consecutive alkylation of 9-isopropyl-6-phenyl-9H-purine with methyl 2-diazo-3,3,3-trifluoropropionate and diethyl diazomalonate proceeds at the phenyl substituent firstly via ortho-C–H activation under chelation-assistance of the purine core, followed by classical electrophilic metal carbenoid insertion to the C−H bond of a malonate moiety.

Keywords: carbenoids, C–H functionalization, diazo compounds, organofluorine compounds, homogeneous catalysis, nitrogen heterocycles, purines.

Language: English

DOI: 10.1016/j.mencom.2020.07.029

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