Abstract
Cyclization of substituted quinone imines and diazabutadiene derivatives of aminophenols affords 4aH-phenoxazine or 4H-1,4-benzoxazine derivatives, which are finally transformed into the following fused heterocycles: the stable 1,4,6,8-tetra(tert-butyl)phenoxazin-10-yl radical and 7a,14a,15a, 15b-tetrahydro-14,16-dioxa-5,9-diaza-8,15-ethenohexaphene and 5a,6,11a, 12-tetrahydro[1,4]benzoxazino[3,2-b][1,4]benzoxazine derivatives. The influence of the substituents on the pathways of the reactions of intermediate benzoxazines and phenoxazines, such as oxidation, [2+4] dimerization, and the closure of the second ring, was studied. The structures of the fused heterocycles were determined by X-ray diffraction, NMR spectroscopy, and ESR.
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2491–2496, November, 2005.
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Abakumov, G.A., Druzhkov, N.O., Kurskii, Y.A. et al. Quinone imines and aminophenols as precursors of new heterocycles. Russ Chem Bull 54, 2571–2577 (2005). https://doi.org/10.1007/s11172-006-0157-7
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DOI: https://doi.org/10.1007/s11172-006-0157-7