DIELS-ALDER REACTION WITH CYCLIC SULFONES. 9. SYNTHESIS OF 10-OXO-1H-TETRAHYDROFLUORENO[2,1-<i>b</i>]THIOPHENE DIOXIDES

Authors

  • Э. Э. Шульц N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, Novosibirsk 630090
  • Г. Н. Андреев M. K. Ammosov Yakutsk State University, Yakutsk 677000
  • M. М. Шакиров N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, Novosibirsk 630090
  • И. Ю. Багрянская N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, Novosibirsk 630090
  • Г. А. Толстиков N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, Novosibirsk 630090

DOI:

https://doi.org/10.1007/7212

Keywords:

benzo[b]thiophene dioxides, fluoreno[2, 1-b]thiophene dioxides, intramolecular Friedel-Crafts acylation, Diels-Alder reaction

Abstract

The treatment of 5-aryl-4',6'-dioxo-2,3,3a,4,5,6-hexahydrospiro-[benzothiophene-4,5'-1,3-dioxane] 1,1-dioxides with boron trifluoride  etherate  in  dichloroethane leads to the formation of products of intramolecular acylation, namely, the corresponding 10-oxo-1H-5,5a,10a,10b-tetrahydrofluoreno-[2,1-b]thiophene dioxides. In all cases, 5-aryl-4-carboxyhexahydrobenzo[b]thiophene 1,1-dioxides were also isolated. The product ratio depends on the structure of the aromatic substituent at C(5) of the spiro- adducts. The structure of 4-carboxy-5-(2-methoxyphenyl)-7-methyl-2,3,3a,4,5,6-hexahydro-benzo[b]thiophene 1,1-dioxide was confirmed by X-ray diffraction structural analysis.

How to Cite
Shults, E. E.; Andreev, G. N.; Shakirov, M. M.; Bagryanskaya, I. Yu.; Tolstikov, G. A.  Chem. Heterocycl. Compd. 2008, 44, 1220. [Khim. Geterotsikl. Soedin. 2008, 1503.]

For this article in the English edition see DOI 10.1007/s10593-009-0174-1

 

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Published

2022-11-25

Issue

No. 10 (2008)

Section

Original Papers