Solvent Moisture-Controlled Self-Assembly of Fused Benzoimidazopyrrolopyrazines with Different Ring’s Interposition |
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Authors: | Svetlana V Martynovskaya Arsalan B Budaev Igor A Ushakov Tatyana N Borodina Andrey V Ivanov |
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Institution: | A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky St., 664033 Irkutsk, Russia; (S.V.M.); (A.B.B.); (I.A.U.); (T.N.B.) |
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Abstract: | This article shows that two extremely important families of fused heterocyclic assemblies, namely 6-methylbenzo4,5]imidazo1,2-a]pyrrolo2,1-c]pyrazine and 5a-methyl-5a,6-dihydro-5H,12H-benzo4,5]imidazo1,2-a]pyrrolo1,2-d]pyrazine, can be synthesized from only two available building blocks (N-allenylpyrrole-2-carbaldehyde and o-phenylenediamine) by controlling only one reaction parameter (water content of the medium). It should be emphasized that the latter class of compounds (with an a/d arrangement) is previously unknown. If the allene group is introduced not into the starting compound, but during the reaction (in superbase media), a heterocyclic ensemble, 5-methylbenzo4,5]imidazo1,2-a]pyrrolo2,1-c]pyrazines, with a different position of the methyl group is formed. |
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Keywords: | aldehydes allenes cyclization heterocycles |
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