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Methyl 3-amino-1H-indole-2-carboxylates in the synthesis of 5H-pyrimido[5,4-b]indole derivatives

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Abstract

Reactions of methyl 3-amino-1H-indole-2-carboxylates with aryl isocyanates, aryl isothiocyanates, and cyanamides led to the formation of 5H-pyrimido[5,4-b]indole derivatives. In the reaction with isocyanates formed 3-aryl-1H-pyrimido[5,4-b]indole-2,4(3H,5H)-diones that were involved into the alkylation at two nitrogen atoms. The reaction with isothiocyanates afforded 3-aryl-2-thioxo-2,3-dihydro-1H-pyrimido[5,4-b]indol-4(5H)-ones undergoing alkylation at the sulfur atom. The reactions with benzoylcyanamide and N-(4,6-dimethylpyrimidin-2-yl)cyanamide resulted in N-(4-oxo-4,5-dihydro-3H-pyrimido-[5,4-b]indol-2-yl)benzamides and 2-(4,6-dimethylpyrimidin-2-ylamino)-3H-pyrimido[5,4-b]indol-4(5H)-ones respectively.

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Authors and Affiliations

  1. Voronezh State University, Voronezh, 394006, Russia

    A. S. Shestakov, Kh. S. Shikhaliev & O. E. Sidorenko

  2. InterBioScreen, Chernogolovka, Russia

    V. G. Kartsev

  3. Belgorod State University, Belgorod, Russia

    S. V. Simakov

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  1. A. S. Shestakov
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  2. Kh. S. Shikhaliev
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  3. O. E. Sidorenko
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  4. V. G. Kartsev
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  5. S. V. Simakov
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Correspondence to A. S. Shestakov.

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Original Russian Text © A.S. Shestakov, Kh.S. Shikhaliev, O.E. Sidorenkoa V.G. Kartsev, S.V. Simakov, 2009, published in Zhurnal Organicheskoi Khimii, 2009, Vol. 45, No. 5, pp. 790–795.

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Shestakov, A.S., Shikhaliev, K.S., Sidorenko, O.E. et al. Methyl 3-amino-1H-indole-2-carboxylates in the synthesis of 5H-pyrimido[5,4-b]indole derivatives. Russ J Org Chem 45, 777–782 (2009). https://doi.org/10.1134/S1070428009050224

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