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Diels-alder reaction with cyclic sulfones. 9.* Synthesis of 10-oxo-1h-tetrahydrofluo-reno[2,1-b]thiophene dioxides*2

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Chemistry of Heterocyclic Compounds Aims and scope

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.

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Authors and Affiliations

  1. N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, Novosibirsk, 630090, Russia

    E. E. Shults, M. M. Shakirov, I. Yu. Bagryanskaya & G. A. Tolstikov

  2. M. K. Ammosov Yakutsk State University, Yakutsk, 677000, Russia

    G. N. Andreev

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  1. E. E. Shults
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  2. G. N. Andreev
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  3. M. M. Shakirov
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  4. I. Yu. Bagryanskaya
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  5. G. A. Tolstikov
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Correspondence to E. E. Shults.

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*2Dedicated to Academician of the Russian Academy of Sciences B. A. Trofimov on his 70th jubilee.

*For Communication 9 see [1].

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1503–1512, October, 2008.

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Shults, E.E., Andreev, G.N., Shakirov, M.M. et al. Diels-alder reaction with cyclic sulfones. 9.* Synthesis of 10-oxo-1h-tetrahydrofluo-reno[2,1-b]thiophene dioxides*2 . Chem Heterocycl Comp 44, 1220–1228 (2008). https://doi.org/10.1007/s10593-009-0174-1

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  • DOI: https://doi.org/10.1007/s10593-009-0174-1

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