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- Title
Methyl 3-amino-1 H-indole-2-carboxylates in the synthesis of 5 H-pyrimido[5,4- b]indole derivatives.
- Authors
Shestakov, A. S.; Shikhaliev, Kh. S.; Sidorenko, O. E.; Kartsev, V. G.; Simakov, S. V.
- Abstract
Reactions of methyl 3-amino-1 H-indole-2-carboxylates with aryl isocyanates, aryl isothiocyanates, and cyanamides led to the formation of 5 H-pyrimido[5,4- b]indole derivatives. In the reaction with isocyanates formed 3-aryl-1 H-pyrimido[5,4- b]indole-2,4(3 H,5 H)-diones that were involved into the alkylation at two nitrogen atoms. The reaction with isothiocyanates afforded 3-aryl-2-thioxo-2,3-dihydro-1 H-pyrimido[5,4- b]indol-4(5 H)-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-3 H-pyrimido-[5,4- b]indol-2-yl)benzamides and 2-(4,6-dimethylpyrimidin-2-ylamino)-3 H-pyrimido[5,4- b]indol-4(5 H)-ones respectively.
- Subjects
ISOCYANATES; ISOCYANIC acid; ALKYLATION; INDOLE; ORGANIC chemistry; PHYSICAL &; theoretical chemistry
- Publication
Russian Journal of Organic Chemistry, 2009, Vol 45, Issue 5, p777
- ISSN
1070-4280
- Publication type
Article
- DOI
10.1134/S1070428009050224