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

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

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...

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Veröffentlicht in:Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2015-10, Vol.51 (10), p.913-917
Hauptverfasser: Usachev, Sergey A., Popova, Natal’ya V., Moshkin, Vladimir S., Sosnovskikh, Vyacheslav Ya
Format: Artikel
Sprache:eng
Schlagworte:
Chemistry
Chemistry and Materials Science
Organic Chemistry
Pharmacy
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Zusammenfassung: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.
ISSN:0009-3122
1573-8353
DOI:10.1007/s10593-015-1795-1