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4a′-Hydroxy-3′,3′,5,6′,6′,7-hexamethyl-3′,4′,4a′,6′,7′,9a′-hexahydrospiro[indole-3,9′-xanthene]-1′,2,8′(1 H ,2′ H ,5′ H)-trione.

Authors :
Ryzhkova, Yuliya E.
Kalashnikova, Varvara M.
Ryzhkov, Fedor V.
Fakhrutdinov, Artem N.
Elinson, Michail N.
Source :
Molbank; Sep2023, Vol. 2023 Issue 3, pM1721, 7p
Publication Year :
2023

Abstract

Pseudo-multicomponent reactions (Pseudo-MCRs) have led to a variety of compounds with interesting biological properties, especially desirable in the pharmaceutical industry. The isatin nucleus could be considered a privileged scaffold for the design of biologically active substances. Dimedone is an interesting and versatile molecule for most organic transformations, especially one-pot and multicomponent reactions. Xanthene derivatives are still an attractive research field for both academia investigations and industry. In this investigation, a simple and efficient tandem Knoevenagel–Michael protocol with subsequent cyclization for the synthesis of the previously unknown 4a′-hydroxy-3′,3′,5,6′,6′,7-hexamethyl-3′,4′,4a′,6′,7′,9a′-hexahydrospiro[indole-3,9′-xanthene]-1′,2,8′(1H,2′H,5′H)-trione was elaborated. The suggested method is based on the pseudo-MCR of 5,7-dimethylisatin and dimedone. The structure of the earlier unknown compound was proven using <superscript>1</superscript>H, <superscript>13</superscript>C-NMR, and IR spectroscopy, mass spectrometry, and elemental analysis. To compare the developed protocol with the existing ones, unsubstituted spiro[indole-3,9′-xanthene] was synthesized. Its structure has been proven using two-dimensional (2D) NMR spectroscopy techniques. [ABSTRACT FROM AUTHOR]

Details

Language :
English
ISSN :
14228599
Volume :
2023
Issue :
3
Database :
Complementary Index
Journal :
Molbank
Publication Type :
Academic Journal
Accession number :
172417161
Full Text :
https://doi.org/10.3390/M1721