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

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 Full article

Journal

Molbank
ISSN: 1422-8599

Output data

Year: 2023, Volume: 2023, Number: 3, Article number : M1721, Pages count : DOI: 10.3390/m1721

Authors

Ryzhkova Yuliya E. ¹ , Kalashnikova Varvara M. ^2,1 , Ryzhkov Fedor V. ¹ , Fakhrutdinov Artem N. ¹ , Elinson Michail N. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry Russian Academy of Sciences, 47 Leninsky Prospekt, 119991 Moscow, Russia
2	Higher Chemical College at the Russian Academy of Sciences, D. Mendeleev University of Chemical Technology of Russia, 9 Miusskaya Sq., 125047 Moscow, Russia

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 1H, 13C-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.

Ryzhkova Y.E. , Kalashnikova V.M. , Ryzhkov F.V. , Fakhrutdinov A.N. , Elinson M.N.
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
Molbank. 2023. V.2023. N3. M1721 . DOI: 10.3390/m1721 WOS Scopus OpenAlex

≡ Web of science:	WOS:001076859200001
≡ Scopus:	2-s2.0-85172781366
≡ OpenAlex:	W4386558441