Abstract
The reactions of benzene-1,2-diamine with 5-substituted 2-(alkylsulfanyl)-4-methylpyrimidin-6(1H)-ones and 2-(propylsulfanyl)- and 5-iodo-2-(propylsulfanyl)-3,4-dihydroquinazolines at 175–185°C under solvent-free conditions unexpectedly afforded benzo[4,5]imidazo[1,2-a]pyrimidine, benzo[4,5]imidazo[2,1-b]-quinazoline, and 2,2′-(benzene-1,2-diyldiimino)bis[pyrimidin-4(3H)-ones]. The described reaction is the first example of synthesis of these heterocyclic systems by fusion of benzimidazole to pyrimidine or quinazoline and is likely to follow ANRORC mechanism.
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Original Russian Text © A.A. Harutyunyan, 2016, published in Zhurnal Organicheskoi Khimii, 2016, Vol. 52, No. 7, pp. 1018–1023.
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Harutyunyan, A.A. New general synthesis of benzo[4,5]imidazo[1,2-a]pyrimidine and benzo[4,5]imidazo[2,1-b]quinazoline derivatives. Russ J Org Chem 52, 1012–1017 (2016). https://doi.org/10.1134/S1070428016070150
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DOI: https://doi.org/10.1134/S1070428016070150