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[3+2] Cycloaddition Reactions to Indolyl- and Pyrrolyl Derivatives of Dinitrobenzofurazan

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Chemistry of Heterocyclic Compounds Aims and scope

The reactions of 4-chloro-5,7-dinitro-4-benzofurazan with indole and pyrrole derivatives, occurring by SNAr–SEAr mechanism, led to the formation of dihetaryls with intramolecular charge transfer. A method was developed for the annelation of pyrrole and dihydropyrrole ring to nitrobenzofurazan fragment by adding unstabilized azomethine ylide to the С=С bond of dinitrobenzofurazan. The structure of nitrobenzofurazan derivatives was studied by X-ray structural analysis, NMR spectroscopy, and quantum-chemical calculations using ab initio and DFT methods.

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The quantum-chemical calculations and resonance spectroscopy studies of the structure and properties of nitrobenzofurazan derivatives were performed with support from the Russian Science Foundation (project No. 14-13-00103).

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Authors and Affiliations

  1. Southern Federal University, 7 Zorge St., Rostov-on-Don, 344090, Russia

    Yu. P. Semenyuk, A. S. Kochubei, P. G. Morozov, O. N. Burov, M. E. Kletskii & S. V. Kurbatov

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  1. Yu. P. Semenyuk
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  2. A. S. Kochubei
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  3. P. G. Morozov
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  4. O. N. Burov
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  5. M. E. Kletskii
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  6. S. V. Kurbatov
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Correspondence to P. G. Morozov.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1881-1891, December, 2014.

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Semenyuk, Y.P., Kochubei, A.S., Morozov, P.G. et al. [3+2] Cycloaddition Reactions to Indolyl- and Pyrrolyl Derivatives of Dinitrobenzofurazan. Chem Heterocycl Comp 50, 1731–1740 (2015). https://doi.org/10.1007/s10593-015-1645-1

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