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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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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DOI: https://doi.org/10.1007/s10593-015-1645-1