Synthesis of 1,3-di[alkoxy(aryloxy)carbonyl]-2-oxo-2,3-dihydroindoles

Márta Porcs-Makkay, G. Argay, A. Kálmán, Gyula Simig

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

Two protocols have been developed for the synthesis of 1,3-di[alkoxy(aryloxy)carbonyl]-2-oxo-2,3-dihydroindoles starting from the corresponding N,O-diacyl derivatives obtained by treatment of 2-oxindoles with chloroformic acid esters and triethylamine. The first is rearrangement of N,O-diacylated compounds in the presence of 4-dimethylaminopyridine to give N,C(3)-diacylated products with identical acyl groups in the two positions. The second involves O-deacylation of the N,O-diacylated compounds, followed by O-acylation and rearrangement resulting N,C(3)-diacylated 2-oxindoles with different acyl groups in the two positions. (C) 2000 Elsevier Science Ltd.

Original languageEnglish
Pages (from-to)5893-5903
Number of pages11
JournalTetrahedron
Volume56
Issue number32
Publication statusPublished - Aug 4 2000

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Acylation
Esters
Derivatives
alkoxyl radical
2-oxindole
4-dimethylaminopyridine
triethylamine
chlorocarbonic acid

Keywords

  • Acylation
  • Indolinones
  • Rearrangements
  • Regio control
  • Tautomerism

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Synthesis of 1,3-di[alkoxy(aryloxy)carbonyl]-2-oxo-2,3-dihydroindoles. / Porcs-Makkay, Márta; Argay, G.; Kálmán, A.; Simig, Gyula.

In: Tetrahedron, Vol. 56, No. 32, 04.08.2000, p. 5893-5903.

Research output: Contribution to journalArticle

Porcs-Makkay, M, Argay, G, Kálmán, A & Simig, G 2000, 'Synthesis of 1,3-di[alkoxy(aryloxy)carbonyl]-2-oxo-2,3-dihydroindoles', Tetrahedron, vol. 56, no. 32, pp. 5893-5903.
Porcs-Makkay, Márta ; Argay, G. ; Kálmán, A. ; Simig, Gyula. / Synthesis of 1,3-di[alkoxy(aryloxy)carbonyl]-2-oxo-2,3-dihydroindoles. In: Tetrahedron. 2000 ; Vol. 56, No. 32. pp. 5893-5903.
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