The synthesis of 3-aryl-3-trifluoromethyl-2,3-dihydro-1H-pyrrolizin-1-ones
Journal Title: Журнал органічної та фармацевтичної хімії; Журнал органической и фармацевтической химии - Year 2019, Vol 17, Issue 1
Abstract
Aim. To develop the efficient method for the synthesis of 3-aryl-3-trifluoromethyl-2,3-dihydro-1H-pyrrolizin-1-ones as promising scaffolds in design of bioactive compounds. Results and discussion. It has been shown that condensation of 3-amino-3-aryl-4,4,4-trifluorobutanoic acid methyl esters with 2,5-dimethoxytetrahydrofuran is a convenient synthetic approach to 4,4,4-trifluoro-3-aryl-3-(1H-pyrrol-1-yl)methylbutanoic acid methyl esters converted to 3-aryl-3-trifluoromethyl-2,3-dihydro-1H-pyrrolizin-1-ones by the intramolecular Friedel-Crafts reaction. Experimental part. By the interaction of 3-amino-3-aryl-4,4,4-trifluorobutanoic acid methyl esters with 2,5-dimethoxytetrahydrofuranin acetic acid at 70 оС 4,4,4-trifluoro-3-aryl-3-(1H-pyrrol-1-yl)methylbutanoic acid methyl esters were obtained and subsequently cyclized into 3-aryl-3-trifluoromethyl-2,3-dihydro-1H-pyrrolizin-1-ones upon treatment with boron tribromide in dichloromethane at room temperature. The structures of the compounds synthesized were confirmed by LCMS, IR and NMR (1H, 13C, 19F) spectroscopic methods. Conclusions. An efficient two step protocol for the synthesis of 3-aryl-3-trifluoromethyl-2,3-dihydro-1H-pyrrolizin-1-ones has been developed. It includes transformation of 3-amino-3-aryl-4,4,4-trifluorobutanoic acid methyl esters into the corresponding 3-(1H-pyrrol-1-yl) derivatives and their further intramolecular cyclization.
Authors and Affiliations
S. V. Melnykov, V. M. Tkachuk, A. M. Grozav, I. Gillaizeau, V. A. Sukach
Keywords
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- EP ID EP659360
- DOI 10.24959/ophcj.19.961
- Views 88
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