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A synthesis of 3-acyl-5-alkyl tetramic acids

โœ Scribed by R.C.F. Jones; S. Sumaria


Publisher
Elsevier Science
Year
1978
Tongue
French
Weight
177 KB
Volume
19
Category
Article
ISSN
0040-4039

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๐Ÿ“œ SIMILAR VOLUMES


Directed metallation of tetramic acids:
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Acyl tetramic acids have been prepared by directed metallation at C-3 of the 4-g-methyl ethers of pyrrolidine-2,4diones, reaction of the vinyl-lithium derivative with aldehydes, and oxidation and hydrolysis of the adducts.

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Boron difluoride complexes of 3-acyl tetramic acids have been isolated from acylation of pyrrolidine-2,4-diones with acid chlorides and boron trifluoride-etherate, or prepared from 3-acyl tetramic acids.

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The Michael addition of R2CuLi or R2CuMgBr to 4-phenyl-3,4,7,8-tetrahydro-6H-pyrido (2, l-c)(1,4)oxazin-1-one 2, readily obtained from 2-cyano-6-phenyloxazolopiperidine 1, led to the formation of alkylated lactones 4a-d in high yield and with complete diastereoselectivity. Transformation of lactones