271-63-6Relevant articles and documents
Ruthenium-Catalyzed Regioselective C(sp2)-H Activation/Annulation of N-(7-Azaindole)amides with 1,3-Diynes Using N-Amino-7-azaindole as the N, N-Bidentate Directing Group
Pati, Bedadyuti Vedvyas,Sagara, Prateep Singh,Ghosh, Asit,Das Adhikari, Gopal Krushna,Ravikumar, Ponneri Chandrababu
, p. 9428 - 9443 (2021)
The ruthenium(II)-catalyzed regioselective annulation of N-(7-azaindole)amides with 1,3-diynes has been demonstrated. Bioactive N-amino-7-azaindole has been used as a new bidentate directing group to furnish an array of 3-alkynylated isoquinolones. Furthermore, the developed protocol works efficiently for both aryl- and heteroaryl-substituted amides producing a range of pharmacologically useful 7-azaindole-based isoquinolones with a wide range of functionality.
Photochemistry of Transient Tautomer of 7-Azaindole H-Bonded Dimer Studied by Two-Step Laser Excitation Fluorescence Measurements
Tokumura, Kunihiro,Watanabe, Yukari,Udagawa, Masahiro,Itoh, Michiya
, p. 1346 - 1350 (1987)
Formation of the monomeric tautomer (7H-pyrrolopyridine) in the photodissociation of the transient groun-state dimeric tautomer, generated via excited-state double proton transfer of 7-azaindole H-bonded dimer in 3-methylpentane (MP), was confirmled by transient absorption and two-step laser excitation (TSLE) fluorescence spectroscopies.The intense XeCl laser pulse (308-nm) excitation of the H-bonded dimer in MP at room temperature produced short- (17 μs) and a long-lived (47 μs) transients.The former and latter were ascribed to the dimeric and monomeric tautomers in the ground state, respectively.It is suggested that the second pulse excitation of the short-lived dimeric tautomer induces efficient dissociation to form a monomeric tautomer in the xcited state together with that in the ground state.One-color (308-nm) biphotonic processes within the XeCl laser pulse are therefore responsible for the long-lived monomeric tautomer in the ground state.The decay of the monomeric tautomer in the dark is attributable to the H-transfer reaction to yield 7-azaindole.Significant deuterium isotope effects were found for H-transfer of the monomeric tautomer as well as for photodissociation of the dimeric tautomer.
Solvation of 7-azaindole in alcohols and water: Evidence for concerted, excited-state, double-proton transfer in alcohols
Chen,Gai,Petrich
, p. 10158 - 10166 (1993)
The proton inventory technique is used for the first time to investigate excited-state proton-transfer processes. The nonradiative pathways of the biological probe, 7-azaindole, in methanol, ethanol, and water are examined. Results in methanol and ethanol demonstrate the involvement of two protons in the transition state for the excited-state double-proton transfer process. These data provide the first experimental evidence suggesting a concerted tautomerization reaction of 7-azaindole in alcohols. The data for 7-azaindole in water are interpreted in terms of a nonradiative pathway that is qualitatively different from that in alcohols. We propose abstraction of the N1 hydrogen by water as a possible nonradiative decay process.
Palladium-catalyzed hydrodefluorination of fluoroarenes
Brodney, Michael A.,Gair, Joseph J.,Giroux, Simon,Grey, Ronald L.
, p. 131 - 146 (2021/06/18)
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Highly Chemoselective Deoxygenation of N-Heterocyclic N-Oxides Using Hantzsch Esters as Mild Reducing Agents
An, Ju Hyeon,Kim, Kyu Dong,Lee, Jun Hee
supporting information, p. 2876 - 2894 (2021/02/01)
Herein, we disclose a highly chemoselective room-temperature deoxygenation method applicable to various functionalized N-heterocyclic N-oxides via visible light-mediated metallaphotoredox catalysis using Hantzsch esters as the sole stoichiometric reductant. Despite the feasibility of catalyst-free conditions, most of these deoxygenations can be completed within a few minutes using only a tiny amount of a catalyst. This technology also allows for multigram-scale reactions even with an extremely low catalyst loading of 0.01 mol %. The scope of this scalable and operationally convenient protocol encompasses a wide range of functional groups, such as amides, carbamates, esters, ketones, nitrile groups, nitro groups, and halogens, which provide access to the corresponding deoxygenated N-heterocycles in good to excellent yields (an average of an 86.8% yield for a total of 45 examples).