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Vol. 30 No. 10 (2018): Vol 30 Issue 10, 2018

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Synthesis of Functionalized Triphenodioxazines via Palladium Catalyzed Cross-Coupling Reactions

https://doi.org/10.14233/ajchem.2018.21477
U.C. Okoro
Department of Pure and Industrial Chemistry, Faculty of Physical Sciences, University of Nigeria, Nsukka 410001, Enugu State, Nigeria
M.A. Ezeokonkwo
Department of Pure and Industrial Chemistry, Faculty of Physical Sciences, University of Nigeria, Nsukka 410001, Enugu State, Nigeria
A. Utime
Department of Pure and Industrial Chemistry, Faculty of Physical Sciences, University of Nigeria, Nsukka 410001, Enugu State, Nigeria
E.U. Godwin-Nwakwasi
Department of Chemistry, College of Natural & Applied Sciences, Gregor University, Uturu, Abia State, Nigeria
F.N. Ibeanu
School of General Studies, Natural Science Unit, University of Nigeria, Nsukka 410001, Enugu State, Nigeria
S.N. Okafor
Department of Pharmaceutical and Medicinal Chemistry, University of Nigeria, Nsukka 410001, Enugu State, Nigeria

Corresponding Author(s) : M.A. Ezeokonkwo

mercy.ezeokonkwo@unn.edu.ng; mercy.ezeokonkwo@yahoo.com

Asian Journal of Chemistry, Vol. 30 No. 10 (2018): Vol 30 Issue 10, 2018

Abstract

In this study, palladium catalyzed cross coupling reaction for the arylation of linear diaza triphenodioxazine is reported. The reaction of 2,5-dibromo-1,4-quinone with two molar equivalents of 2-amino-3-hydroxypyridine in anhydrous basic medium furnished 1,8-diazatriphenodioxazine (9) in good yield. The non aza analogue and parent ring of this ring system was also obtained under similar conditions. 6-Bromo-1,8-diazatriphenodioxazine (10) was formed by bromination of compound 9 in glacial acetic acid. Functionalized aryl derivatives of 9 were obtained by cross coupling reactions between substituted boronic acids and 10 under the catalytic influence of Pd[dppb]Cl2/1,4-bis(2- hydroxy-3,5-di-tert-butylbenzyl)piperazine system.

Keywords

Triphenodioxazines Palladium cross-coupling reactions Aza analogue Suzuki-Miyaura reactions Boronic acids
Okoro, U., Ezeokonkwo, M., Utime, A., Godwin-Nwakwasi, E., Ibeanu, F., & Okafor, S. (2018). Synthesis of Functionalized Triphenodioxazines via Palladium Catalyzed Cross-Coupling Reactions. Asian Journal of Chemistry, 30(10), 2317–2321. https://doi.org/10.14233/ajchem.2018.21477
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