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Synthesis of 6-imino-5-tetrahydro-1H-2-pyrrolylidenhexahydro-2,4-pyrimidinediones as intermediates for the synthesis of C-azanucleosides |
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| Authors: | Ashot Martirosyan Rafael Tamazyan Marina Alexanyan Vahan Martirosyan |
| Institution: | a Institute of Fine Organic Chemistry, National Academy of Sciences RA, Azatutyan Avenue 26, 0014 Yerevan, Armenia b Molecular Structure Research Center, National Academy of Sciences RA, Azatutyan Avenue 26, 0014 Yerevan, Armenia c Emory University School of Medicine, Veterans Affairs, Medical Center 1670, Clairmont Road, 151-H Decatur, Georgia 30033-4004, USA |
| Abstract: | The method for the synthesis of 6-imino-5-tetrahydro-1H-2-pyrrolylidenhexahydro-2,4-pyrimidinediones is described. It is shown that the reaction of phosphorus trichloride, 2-pyrrolidones and 6-aminopyrimidines brings to condensation producing 6-imino-5-tetrahydro-1H-2-pyrrolylidenhexahydro-2,4-pyrimidinediones as intermediates for the synthesis of C-azanucleosides. The reaction of 6-imino-1,3-dimethyl-5-tetrahydro-2-pyrrolylidenhexahydro-2,4-pyrimidinedione with benzoyl chloride produces 10-benzoyl-2,4-dimethyl-6-phenyl-1,2,3,4,8,9-hexahydropyrimido5,4-e]pyrrolo1,2-c]pyrimidine-1,3-dione. A method for the selective reduction of the carbomethoxy group of methyl 5-(4-imino-1,3-dimethyl-2,6-dioxohexahydro-5-pyrimidinyliden)-2-pyrrolidine carboxylate by system NaBH4/1,4dioxane/CoCl2/PEG-400 is described. |
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