Synthesis of hexa-, tetra-, and dihydroxanthene derivatives from salicylaldehyde aminals |
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Authors: | L. Yu. Ukhin V. A. Kharlanov E. V. Solomovich O. V. Shishkin |
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Affiliation: | (1) Institute of Physical and Organic Chemistry, Rostov State University, 194/2 prosp. Stachki, 344090 Rostov-on-Don, Russian Federation;(2) A. N. Nesmayanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 117813 Moscow, Russian Federation;(3) Institute for Single Crystals, National Academy of Sciences of Ukraine, 60 prosp. Lenina, 310001 Kharkov, Ukraine |
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Abstract: | Salicylaldehyde aminals react with cyclohexanone upon heating to form tetrahydroxanthene derivatives. The structure of one of these derivatives,viz., 5,7-dichloro-4a-morpholino-1,2,3,4-tetrahydro-4aH-xanthene, was established by X-ray diffraction analysis. The scheme of the reaction was suggested, which involves cycloaddition of intermediateo-methylenequinone (from aminal) and enamine (from cyclohexanone). The reactions of salicylaldehyde aminals with enamines that formed from cyclohexanone can successively afford derivatives of hexahydroxanthene, tetrahydroxanthene, and dihydroxanthene. Procedures were developed for the synthesis of these compounds.N-Substituted 4a-amino-7-nitro-1,2,3,4-tetrahydro-4aH-xanthenes were also prepared by the reactions of dialkylammonium 2-formyl-4-nitrophenoxides with the above-mentioned enamines. Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 959–965, May, 1999. |
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Keywords: | salicylaldehyde aminals cyclohexanone enamines o-methylenequinones dialkylamunonium 2-formyl-4-nitrophenoxides cycloaddition hexa-, tetra-, and dihydroxanthene derivatives |
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