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Vol. 27 No. 8 (2015): Vol 27 Issue 8

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Synthesis of Novel Angular Diazaphenoxazinone Derivatives via Palladium Catalyzed Buchwald-Hartwig Amidation Protocols

https://doi.org/10.14233/ajchem.2015.18874
M.E. Odaa
Department of Pure and Industrial Chemistry, University of Nigeria, Nsukka, Nigeria
U.C. Okoro
Department of Pure and Industrial Chemistry, University of Nigeria, Nsukka, Nigeria
D.I. Ugwu
Department of Pure and Industrial Chemistry, University of Nigeria, Nsukka, Nigeria

Corresponding Author(s) : D.I. Ugwu

izuchukwu.ugwu@unn.edu.ng

Asian Journal of Chemistry, Vol. 27 No. 8 (2015): Vol 27 Issue 8

Abstract

The synthesis of new amido derivatives of angular diazaphenoxazinone via tandem amidation protocol is reported. This was achieved by the condensation of 4,5-diamino-6-hydroxypyrimidine (7) with 2,3-dichloro-1,4-naphthoquinone (8) in anhydrous basic medium to furnish the key intermediate, 11-amino-6-chloro-8,10-diazabenzo[a]phenoxazin-5-one (9). Palladium catalyzed amidation reaction of 11-amino-6-chloro-8,10-diazabenzo[a]phenoxazin-5-one (9) with different amides (12a-c) (benzamide, acetamide, salicylamide and 4-nitrobenzamide) in the presence of palladium(II) acetate, triphenyl phosphine (PPh3), water and tertiary butanol at 110 °C for 3 h gave the new amido derivatives 13a-c. Structures of the new compounds were established by elemental analysis, UV, FTIR, 1H NMR and 13C NMR.

Keywords

Synthesis Phenoxazines Phenoxazinone Diazaphenoxazinone Tandem catalysis
Odaa, M., Okoro, U., & Ugwu, D. (2015). Synthesis of Novel Angular Diazaphenoxazinone Derivatives via Palladium Catalyzed Buchwald-Hartwig Amidation Protocols. Asian Journal of Chemistry, 27(8), 3069–3073. https://doi.org/10.14233/ajchem.2015.18874
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