THE SYNTHESIS OF NEW SPIROLACTONES FROM SUBSTITUTED ISATINS

THE SYNTHESIS OF NEW SPIROLACTONES FROM SUBSTITUTED ISATINS

Interaction of N-ethyl isatin 3 with dimethyl acetylenedicarboxylate in the presence triphenylphosphine has led to good selectivity of methyl 1'-ethyl-4-methoxy-2',5-dioxo-5H-spiro[furan-2,3'-indoline]-3-carboxylate 4 formation. Similar yields of spirolactones 6,8 were obtained by add...

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Bibliographic Details
Main Authors: Natalia Sucman, Vsevolod Pogrebnoi, Mykola Obushak, Elena Melnic, Victor Kravtsov, Fliur Macaev
Format: Article
Language:English
Published: Academy of Sciences of Moldova, Institute of Chemistry 2015-06-01
Series:Chemistry Journal of Moldova: General, Industrial and Ecological Chemistry
Subjects:
spirolactones
isatins
triphenylphosphine
dimethyl acetylenedicarboxylate.
Online Access:http://www.cjm.asm.md/sites/default/files/article_files/ChemJMold201510(1)_64-70_Macaev.pdf
Description
Summary:Interaction of N-ethyl isatin 3 with dimethyl acetylenedicarboxylate in the presence triphenylphosphine has led to good selectivity of methyl 1'-ethyl-4-methoxy-2',5-dioxo-5H-spiro[furan-2,3'-indoline]-3-carboxylate 4 formation. Similar yields of spirolactones 6,8 were obtained by addition of dimethyl acetylenedicarboxylate to 5-bromo functionalized isatins 5,7. However, reaction of N-butyl isatin 9 resulted in formation of an inseparable mixture of compounds. Treatment of N-benzyl isatin 10 and dimethyl acetylenedicarboxylate with triphenylphosphine proceeded with reduced selectivity of the spirooxindole 11 formation.
ISSN:1857-1727
2345-1688

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