The synthesis of new spirolactones from substituted isatins
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543.9+547 (1)
Analiza cu ajutorul reacțiilor biologice și biochimice. Metode biologice utilizate în scopuri analitice (1)
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SUCMAN, Natalia; POGREBNOI, Vsevolod; OBUSHAK, Mykola; MELNIC, Elena; KRAVTSOV, Viktor; MACAEV, Fliur. The synthesis of new spirolactones from substituted isatins . In: Chemistry Journal of Moldova. 2015, nr. 1(10), pp. 64-70. ISSN 1857-1727.
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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

CZU: 543.9+547
DOI: 10.19261/cjm.2015.10(1).09
Pag. 64-70

Sucman Natalia1, Pogrebnoi Vsevolod1, Obushak Mykola2, Melnic Elena3, Kravtsov Viktor3, Macaev Fliur1
 
1 Institute of Chemistry of the Academy of Sciences of Moldova,
2 Львовский национальный университет имени Ивана Франко,
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, triphenylphosphine, dimethyl acetylenedicarboxylate.