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Bisindoles. 43*. Dipyrroloquinoxalines. 2*. Synthesis of the bis-analogs of the fischer aldehyde under vilsmeier conditions

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Chemistry of Heterocyclic Compounds Aims and scope

The Vilsmeier formylation of bifunctional Fischer base analogs in the dipyrrolobenzoquinoxaline and indoloindole series was studied with various substrate–Vilsmeier complex ratios. The isomeric Fischer bases of the indoloindole series were formylated smoothly with the formation of the corresponding diformyl derivatives: 2,7-di(formylmethylidene)-1,3,3,6,8,8-hexamethylindolino[7,6-g]indoline and 2,9-di(formylmethylidene)-1,1,3,8,10,10-hexamethylindolino[4,5-e]indoline. In the case of 1,4,5,8-tetra-hydro-1,1,8,8-tetramethyl-2,7-dimethylidenebenzo[g]dipyrrolo[1,2,3-de:3,2,1-ij]quinoxaline reaction at 35°C with a large excess of the Vilsmeier complex (1:45), the diformyl derivative 2,7-di-(formylmethylidene)-1,4,5,8-tetrahydro-1,1,8,8-tetramethylbenzo[g]dipyrrolo[1,2,3-de:3,2,1-ij]quin-oxaline was obtained with a 67% yield. At 60°C and reagent molar ratio of 1:5, a cyanine dye of unknown structure was evidently formed.

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References

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Authors and Affiliations

  1. Ivane Javakhishvili Tbilisi State University, 1 Chavchavadze Ave., Tbilisi, 0218, Georgia

    Sh. A. Samsoniya, M. V. Trapaidze & N. N. Nikoleishvili

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  1. Sh. A. Samsoniya
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  2. M. V. Trapaidze
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  3. N. N. Nikoleishvili
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Correspondence to Sh. A. Samsoniya.

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*For Communications 42 and 1, see [1, 2].

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 580-584, April, 2013.

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Samsoniya, S.A., Trapaidze, M.V. & Nikoleishvili, N.N. Bisindoles. 43*. Dipyrroloquinoxalines. 2*. Synthesis of the bis-analogs of the fischer aldehyde under vilsmeier conditions. Chem Heterocycl Comp 49, 540–544 (2013). https://doi.org/10.1007/s10593-013-1279-0

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  • DOI: https://doi.org/10.1007/s10593-013-1279-0

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