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STEREOSELECTIVE ADDITION OF ETHYL 3-MORPHOLINO(PIPERIDINO)CROTONATES TO 2-TRIHALOMETHYL-3-NITRO-2H-CHROMENES. SYNTHESIS OF 4-ACETONYL-3-NITROCHROMANS

Владислав Ю. Коротаев, Игорь Б. Кутяшев, Алексей Ю. Барков, Вячеслав Я. Сосновских
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Abstract


Tertiary enamines of acetoacetic ester, obtained with morpholine and piperidine, add to 2-R1-3-nitro-2Н-chromenes (R1 = CF3, CCl3, Ph) via the vinylogue β-methyl group and give the respective cis,trans-2,3,4-trisubstituted chromans, the stereoconfiguration of which was established by X-ray structural analysis. Acidic hydrolysis of these compounds was accompanied by decarboxylation and produced 4-acetonyl-3-nitrochromans with retention of configuration.

How to Cite
Korotaev, V. Yu.; Kutyashev, I. B.; Barkov, A. Yu.; Sosnovskikh, V. Ya. Chem. Heterocycl. Compd. 2015, 51, 440. [Khim. Geterotsikl. Soedin. 2015, 51, 440.]

For this article in the English edition see DOI 10.1007/s10593-015-1718-1


Keywords


3-nitro-2Н-chromenes; push-pull enamines; chromans; hydrolysis; stereochemistry

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