The synthesis of new spirolactones from substituted isatins
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Анализ посредством биологических и биохимических реакций. Биологические методы, применяемые для аналитических целей (9)
Органическая химия (475)
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SUCMAN, Natalia, POGREBNOI, Vsevolod, OBUSHAK, Mykola, MELNIK, E., KRAVTSOV, Victor, MAKAEV, Fliur. The synthesis of new spirolactones from substituted isatins . In: Chemistry Journal of Moldova, 2015, nr. 1(10), pp. 64-70. ISSN 1857-1727. DOI: https://doi.org/10.19261/cjm.2015.10(1).09
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Chemistry Journal of Moldova
Numărul 1(10) / 2015 / ISSN 1857-1727 /ISSNe 2345-1688

The synthesis of new spirolactones from substituted isatins
DOI: https://doi.org/10.19261/cjm.2015.10(1).09
CZU: 543.9+547

Pag. 64-70

Sucman Natalia1, Pogrebnoi Vsevolod1, Obushak Mykola2, Melnik E.3, Kravtsov Victor3, Makaev Fliur1
 
1 Institute of Chemistry of the Academy of Sciences of Moldova,
2 Ivan Franko National University of Lviv,
3 Institute of Applied Physics, Academy of Sciences of Moldova
 
Disponibil în IBN: 15 iulie 2015


Rezumat

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.

Cuvinte-cheie
spirolactones, isatins, dimethyl acetylenedicarboxylate.,

triphenylphosphine