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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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
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spelling doaj-9aa43b42790846d8aa5ea433a496c10a2021-07-02T05:27:43ZengAcademy of Sciences of Moldova, Institute of ChemistryChemistry Journal of Moldova: General, Industrial and Ecological Chemistry1857-17272345-16882015-06-011016470THE SYNTHESIS OF NEW SPIROLACTONES FROM SUBSTITUTED ISATINSNatalia Sucman0Vsevolod Pogrebnoi1Mykola Obushak2Elena Melnic3Victor Kravtsov4Fliur Macaev5Institute of Chemistry of the Academy of Sciences of MoldovaInstitute of Chemistry of the Academy of Sciences of MoldovaIvan Franko National University of LvivInstitute of Applied Physics, Academy of Sciences of MoldovaInstitute of Applied Physics, Academy of Sciences of MoldovaInstitute of Chemistry of the Academy of Sciences of MoldovaInteraction 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.http://www.cjm.asm.md/sites/default/files/article_files/ChemJMold201510(1)_64-70_Macaev.pdfspirolactonesisatinstriphenylphosphinedimethyl acetylenedicarboxylate.
collection DOAJ
language English
format Article
sources DOAJ
author Natalia Sucman
Vsevolod Pogrebnoi
Mykola Obushak
Elena Melnic
Victor Kravtsov
Fliur Macaev
spellingShingle Natalia Sucman
Vsevolod Pogrebnoi
Mykola Obushak
Elena Melnic
Victor Kravtsov
Fliur Macaev
THE SYNTHESIS OF NEW SPIROLACTONES FROM SUBSTITUTED ISATINS
Chemistry Journal of Moldova: General, Industrial and Ecological Chemistry
spirolactones
isatins
triphenylphosphine
dimethyl acetylenedicarboxylate.
author_facet Natalia Sucman
Vsevolod Pogrebnoi
Mykola Obushak
Elena Melnic
Victor Kravtsov
Fliur Macaev
author_sort Natalia Sucman
title THE SYNTHESIS OF NEW SPIROLACTONES FROM SUBSTITUTED ISATINS
title_short THE SYNTHESIS OF NEW SPIROLACTONES FROM SUBSTITUTED ISATINS
title_full THE SYNTHESIS OF NEW SPIROLACTONES FROM SUBSTITUTED ISATINS
title_fullStr THE SYNTHESIS OF NEW SPIROLACTONES FROM SUBSTITUTED ISATINS
title_full_unstemmed THE SYNTHESIS OF NEW SPIROLACTONES FROM SUBSTITUTED ISATINS
title_sort synthesis of new spirolactones from substituted isatins
publisher Academy of Sciences of Moldova, Institute of Chemistry
series Chemistry Journal of Moldova: General, Industrial and Ecological Chemistry
issn 1857-1727
2345-1688
publishDate 2015-06-01
description 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.
topic spirolactones
isatins
triphenylphosphine
dimethyl acetylenedicarboxylate.
url http://www.cjm.asm.md/sites/default/files/article_files/ChemJMold201510(1)_64-70_Macaev.pdf
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