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

Authors

  • Владислав Ю. Коротаев Institute of Natural Sciences, Ural Federal University named after first President of Russia B. N. Yeltsin, 51 Lenina Ave., Yekaterinburg 620000, Russia
  • Игорь Б. Кутяшев Institute of Natural Sciences, Ural Federal University named after first President of Russia B. N. Yeltsin, 51 Lenina Ave., Yekaterinburg 620000, Russia
  • Алексей Ю. Барков Institute of Natural Sciences, Ural Federal University named after first President of Russia B. N. Yeltsin, 51 Lenina Ave., Yekaterinburg 620000, Russia
  • Вячеслав Я. Сосновских Institute of Natural Sciences, Ural Federal University named after first President of Russia B. N. Yeltsin, 51 Lenina Ave., Yekaterinburg 620000, Russia

DOI:

https://doi.org/10.1007/2326

Keywords:

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

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

Author Biography

Владислав Ю. Коротаев, Institute of Natural Sciences, Ural Federal University named after first President of Russia B. N. Yeltsin, 51 Lenina Ave., Yekaterinburg 620000, Russia

Зав. кафедрой органической химии Института естественных наук Уральского федерального университета

Downloads

Published

2015-05-18

Issue

Vol. 51 No. 5 (2015)

Section

Original Papers