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SYNTHESIS OF trans,trans-2,3,4-TRISUBSTITUTED CHROMANES FROM 3-NITRO-2Н-CHROMENES AND ENAMINES OF ACETOACETIC ESTERAND ACETYLACETONE. A NEW TYPE OF CONFIGURATIONALLY STABLE ATROPISOMERS

Владислав Ю. Коротаев, Алексей Ю. Барков, Марина А. Ежикова, Михаил И. Кодесс, Вячеслав Я. Сосновских
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Abstract


Enamines of acetoacetic ester and acetylacetone added at the activated double bond of 2-R1-3-nitro-2Н-chromenes (R1 = CF3, CCl3, Ph) with their central α-С atoms, forming trans,trans-2,3,4-trisubstituted chromanes. The adducts obtaind from acetylacetone enamines represented mixtures of similar amounts of configurationally stable atropisomers, the formation of which was linked to hindered rotation around the C(sp3)–C(sp2) bond. A reaction with enamines of acetoacetic ester led practically exclusively to a single anti-atropisomer.

How to Cite
Korotaev, V. Yu.; Barkov, A. Yu.; Ezhikova, M. A.; Kodess, M. I.; Sosnovskikh, V. Ya. Chem. Heterocycl. Compd. 2015, 51, 531. [Khim. Geterotsikl. Soedin. 2015, 51, 531.]

For this article in the English edition see DOI 10.1007/s10593-015-1733-2

 


Keywords


3-nitro-2Н-chromenes; push-pull enamines; chromanes; atropisomerism; nucleophilic addition

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