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Research Paper | Chemistry | Volume 6 Issue 4, April 2017 | Pages: 2001 - 2007 | New Zealand
Synthesis of 6-Anilino Derivatives of benzo[a]phenoxazin-5-one and related Aza Analogues via Palladium-catalyzed Buchwald-Hartwig Amination Reaction
Abstract: The synthesis of new 6-anilino derivatives of angular phenoxazine dye was thoroughly investigated. This was accomplished by the condensation of 2-aminophenol with 2, 3-dichloro-1, 4-naphthoquinone in an alkaline medium to furnish a good yield of the intermediate, 6-chlorobenzo [a]phenoxazine-5-one (6). BuchwardHartwig cross-coupling of the intermediate with various amines, viz 2-amino-4-methylpyridine, 2-aminopyrazine, 2-amino-5-nitropyridine, 2-aminopyridazine, 2-amino-3-hydroxypyridine, aniline, 4-nitroaniline, 4-aminophenol and 2-aminophenol via water-mediated catalyst activation protocol in DMF/toluene solvents mixture at a temperature of 110 oC yielded the amino derivatives 6 (a-i) respectively. Structures were established by spectral analyses and micro-analytical data.
Keywords: benzoaphenoxazin-5-one, Buchward-Hartwig amination, condensation, palladium catalysis
How to Cite?: Jude Ikechukwu Ayogu, Ojarikre Enoo, Uchechukwu Chris Okoro, "Synthesis of 6-Anilino Derivatives of benzo[a]phenoxazin-5-one and related Aza Analogues via Palladium-catalyzed Buchwald-Hartwig Amination Reaction", Volume 6 Issue 4, April 2017, International Journal of Science and Research (IJSR), Pages: 2001-2007, https://www.ijsr.net/getabstract.php?paperid=ART20172906, DOI: https://dx.doi.org/10.21275/ART20172906