Abstract
Reactions of methyl 4-methoxy-6-oxo-7,7,7-trihalo-4-heptenoates 1 and 2 with primary amines RNH2, where R = PhCH2, PhCH2CH2, Ph, 4-MeC6H4, 4-MeOC6H4, 4-ClC6H4, 4-BrC6H4, 2-pyridyl, 5-methyl-3-isoxazolyl, 4-NH2C6H4 affording methyl 4-[alkyl(aryl)amino]-6-oxo-7,7,7-trihalo-4-heptenoates 3, 4, in good yields (57-95%), which suffer quantitative intramolecular cyclocondensation to produce 1-alkyl(aryl)-5-(2-oxo-3,3,3-trihalopropylidene)pyrrolidin-2-ones 5, 6, are reported. The structures of the isolated new products were assigned by means of ¹H,13C NMR measurements and mass spectrometry. The Z and E configuration of compounds 3d and 5b respectively were established from X-ray crystallography.
Highlights
We have systematically used the acetals acylation method for synthesis of wide range of 4-alkoxy-1,1,1-trihalo-3-alken2-ones
Our continuing interest in 1,3-dielectrophilic compounds has led us to study a new aspect of the application of the acetal acylation method for producing methyl 4-methoxy-6-oxo-7,7,7-trihalo-4-heptenoates 1 and 2.8
Continuing with our systematic studies on synthesis and application of 4-alkoxy-1,1,1-trihalo-3-alken-2-ones we report an efficient approach for synthesis of a series of 1-[alkyl(aryl)]-5-(3,3,3-trihalo-2-oxopropylidene)pyrrolidin-2-nes from 1 and 2
Summary
We have systematically used the acetals acylation method for synthesis of wide range of 4-alkoxy-1,1,1-trihalo-3-alken2-ones. This study deals with formation of the methyl 4-alkyl[aryl]amino-6-oxo-7,7,7-trihalo-4heptenoates 3 and 4, and their intramolecular cyclisations to new 1-alkyl[aryl]-5-(3,3,3-trihalo-2-oxopropylidene) pyrrolidin-2-ones 5 and 6. The methyl 4-arylamino-6-oxo-7,7,7-trifluoro4-heptenoates 3,d-j were obtained in refluxing MeCN or at room temperature, by addition of equimolar amount of Et3N or lutidine (Table 1, Supplementary Information).
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