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SYNTHESIS OF 4-ARYL-6-METHYL-7a-(TRIFLUOROMETHYL)-2,4a,5,6,7,7a-HEXAHYDROPYRANO[2,3-c]PYRROL-2-ONES FROM 4-ARYL-6-(TRIFLUOROMETHYL)-2-PYRONES, SARCOSINE, AND FORMALDEHYDE

Сергей А. Усачев, Наталья В. Попова, Владимир С. Мошкин, Вячеслав Я. Сосновских
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Abstract


4-Aryl-6-(trifluoromethyl)-2-pyrones reacted with the nonstabilized azomethine ylide obtained from sarcosine and formaldehyde under reflux in benzene for 6 h, resulting in [3+2] cycloaddition that gave 4-aryl-6-methyl-7a-(trifluoromethyl)-2,4a,5,6,7,7a-hexahydropyrano[2,3-c]pyrrol-2-ones in 42–56% yields. In the case of 4-aryl-3-carbethoxy-6-(trifluoromethyl)-2-pyrones, besides the respective pyrano-[2,3-c]pyrrolidines (66–71% yields) also 4-aryl-1-methyl-2-(trifluoromethyl)pyrroles were isolated as minor products.

How to Cite
Usachev, S. A.; Popova, N. V.; Moshkin, V. S.; Sosnovskikh, V. Ya. Chem. Heterocycl. Compd. 2015, 51, 913. [Khim. Geterotsikl. Soedin. 2015, 51, 913.]

For this article in the English edition see DOI 10.1007/s10593-015-1795-1

 


Keywords


azomethine ylides; pyrano[2,3-c]pyrrolidines; 2-pyrones; pyrroles; [3+2] cycloaddition

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