3-NITRO-2-PHENYL-2-(TRIFLUOROMETHYL)-2<i>H</i>-CHROMENES IN REACTION WITH <i>N</i>-METHYLAZOMETHINE YLIDE: STEREOSELECTIVE SYNTHESIS OF 3a,4,4-TRISUBSTITUTED CHROMENO[3,4-<i>c</i>]PYRROLIDINES

Authors

  • Владислав Ю. Коротаев Уральский федеральный университет
  • Игорь Б. Кутяшев Уральский федеральный университет
  • Алексей Ю. Барков Уральский федеральный университет
  • Вячеслав Я. Сосновских Уральский федеральный университет

DOI:

https://doi.org/10.1007/4729

Keywords:

chromeno[3, 4-c]pyrrolidines, 3-nitro-2-phenyl-2-(trifluoromethyl)-2H-chromenes, unstabilized azomethine ylides, 1, 3-dipolar cycloaddition.

Abstract

1,3-Dipolar cycloaddition of unstabilized azomethine ylide obtained in situ from sarcosine and paraform occurred stereoselectively at the double bond of 3-nitro-2-phenyl-2-(trifluoromethyl)-2H-chromenes activated by the presence of nitro group. The synthetic procedure required refluxing in benzene for 2 h and gave chromeno[3,4-c]pyrrolidines with trans configuration of trifluoromethyl group and nitro group as the major products. The structure of the obtained products was confirmed by X-ray structural analysis.

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Published

2018-10-17

Issue

Vol. 54 No. 9 (2018)

Section

Original Papers