Synthesis of isoxazolopyrrolo[2,1-a]isoquinoline, isoxazolo[5',4': 1,2]indolizino[8,7-b]indole, and isoxazolo- [5,4-a]thieno[2,3-g]indolizine derivatives by intramolecular cyclization of hydroxylactams constituting a fragment of the pyrroloisoxazole system

L. V. Lenshmidt, M. S. Ledovskaya, A. G. Larina, A. S. Filatov, A. P. Molchanov, R. R. Kostikov, A. V. Stepakov

Research output: Contribution to journalArticlepeer-review

3 Scopus citations

Abstract

6-Hydroxy-5-[2-(naphthalen-1-yl)ethyl]-3a,5,6,6a-tetrahydro-4H-pyrrolo[3,4-d]isoxazol-4-ones in the presence of boron trifluoride-diethyl ether complex underwent cyclization to benzo[f]isoxazolo[5',4': 3,4]- pyrrolo[2,1-a]isoquinoline derivatives as mixtures of two diastereoisomers. Analogous cyclization of 6-hydroxy-5-(naphthalen-1-ylmethyl)-3a,5,6,6a-tetrahydro-4H-pyrrolo[3,4-d]isoxazol-4-ones gave benzo[de]isoxazolo[ 5',4': 3,4]pyrrolo[2,1-a]isoquinolines as a single diastereoisomer. The cyclization of 6-hydroxy-5-[2-(1Hindol-3-yl)ethyl]-6,6a-dihydro-3aH-pyrrolo[3,4-d]isoxazol-4(5H)-ones catalyzed by Sn(NTf2)4 afforded isoxazolo[ 5',4': 1,2]indolizino[8,7-b]indol-4(12H)-ones in moderate yields. 6-Hydroxy-5-[2-(thiophen-2-yl)ethyl]- 6,6a-dihydro-3aH-pyrrolo[3,4-d]isoxazol-4(5H)-ones were converted to 4,5,10a,10b-tetrahydroisoxazolo- [5,4-a]thieno[2,3-g]indolizin-7(7aH)-one derivatives in the presence of BF3 · Et2O or Sn(NTf2)4.

Original languageEnglish
Pages (from-to)112-125
Number of pages14
JournalRussian Journal of Organic Chemistry
Volume54
Issue number1
DOIs
StatePublished - 2018

Scopus subject areas

  • Organic Chemistry

Keywords

  • 1,3-DIPOLAR CYCLOADDITION
  • ACYLIMINIUM ION CYCLIZATION
  • ALKALOID (+/-)-CRISPINE-A
  • INHIBITORS
  • ISOQUINOLINE ALKALOIDS
  • ISOXAZOLOPYRROLOISOQUINOLINES
  • LAMELLARIN ALKALOIDS
  • PORTULACA-OLERACEA
  • SKELETON
  • TOPOISOMERASE-I

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