A 53 An unusual aromatisation of dihydropyrimidines facilitated by reduction of the nitro group [Electronic resource] / G. L. Rusinov, E. B. Gorbunov, V. N. Charushin, O. N. Chupakhin // Tetrahedron Letters. - 2007. - Vol. 48, № 33. - P5873-5876 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: An unusual aromatisation of the dihydropyrimidine fragment in 6-nitro-7-substituted-4,7-dihydro-1,2,4-triazolo[1,5-a]pyrimidines has first been found to occur in parallel with reduction of the nitro group using a number of reducing agents. \\\\Expert2\\nbo\\Tetrahedron Letters\\2007, v. 48, p.5873.pdf |
D 46 Design of fused systems based on sigma(H)-adducts of 6-nitro-1,2,4-triazolo[1,5-a]pyrimidine with pi-excessive heteroaromatic compounds [Electronic resource] / E. B. Gorbunov, G. L. Rusinov, O. N. Chupakhin, V. N. Charushin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2009. - Vol. 58, № 6. - P1309-1314 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: A new method was developed for the construction of tetra- and pentacyclic fused systems based on sigma(H)-adducts of 6-nitro-1,2,4-triazolo[1,5-a]pyrimidine with pi-excessive heteroaromatic compounds. The method involves the reduction of the nitro group accompanied by the aromatization of the dihydropyrimidine ring and followed by the cyclocondensation of the amino derivative with aldehydes \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2009, 58 (6), 1309-1314.pdf |
S 98 Synthesis of podands with dihydropyrimidine fragments based on polyethers with terminal acetoacetamide groups [Electronic resource] / E. S. Radionava, O. V. Fedorova, Yu. A. Titova, G. L. Rusinov, V. N. Charushin // Chemistry of Heterocyclic Compounds. - 2015. - Vol. 51, № 5. - С. 478-482. - Bibliogr. : p. 482 (19 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): ACETOACETAMIDE-CONTAINING PODANDS -- DIHYDROPYRIMIDINE-CONTAINING PODANDS -- ACETYLKETENE Аннотация: Reactions of aliphatic aminopodands having different length of the polyether chain with acetoacetic ester and 2,2,6-trimethyl-4H-1,3-dioxin-4-one were studied. The interaction of aminopodands with acetoacetic ester in toluene upon sonication (60A degrees D) or heating (90A degrees D) gave podands with terminal aminocrotonate fragments. The use of dioxinone at the same temperature allowed to transform aminopodands into aliphatic acetoacetamide-containing podands. An asymmetric podand with 2-pyridone fragment was isolated as byproduct from the reaction of dioxinone with 1,5-diamino-3-oxapentane. A three-component Biginelli reaction of acetoacetamidecontaining podands with benzaldehyde and urea in the presence of catalytic amounts of polyphosphoric acid immobilized on nanosized TiO2-SiO2 oxide surface enabled the synthesis of podands with 1,4-dihydropyrimidin-2-(1De)-one fragments. \\\\expert2\\nbo\\Chemistry of Heterocyclic Compounds\\2015, v.51, N 5, p. 478-482.pdf |
M 94 Multicomponent reactions in the synthesis of dihydropyrimidine-containing podands having tuberculostatic activity / O. V. Fedorova, E. S. Filatova, Y. A. Titova, G. L. Rusinov, V. N. Charushin, M. A. Kravchenko, I. D. Medvinskiy // Russian chemical bulletin. - 2018. - Vol. 67, № 4. - P743-746 Рубрики: ХИМИЧЕСКИЕ НАУКИ |
Features of a multicomponent biginelli reaction involving 3-oxobutanoyl-containing podands, aromatic aldehydes, and 1,2,4-triazol-3-amine / E. S. Filatova, O. V. Fedorova, K. A. Chistyakov [et al.] // Chemistry of heterocyclic compounds. - 2020. - Vol. 56, № 1. - P88-91 Кл.слова (ненормированные): DIHYDROPYRIMIDINE -- MONOSUBSTITUTED PODAND -- PODAND -- TRIAZOLO[1,5-А]PYRIMIDINE -- TRIAZOLO[4,3-А]PYRIMIDINE -- TUBERCULOSTATIC ACTIVITY Аннотация: [Figure not available: see fulltext.] A reaction of 3-oxobutanoyl-containing podands with thiophene-2-carbaldehyde (or benzaldehyde) and 3-amino-1,2,4-triazole gave podands featuring a 4,7-dihydro[1,2,4]triazolo[1,5-а]pyrimidine motif. It was established that the process was accompanied by the formation of [4,3-а]-isomers, which occurred in a slight excess during the synthesis of a podand containing a phenyl group at position 7 and, on the other hand, were observed as the minor products during the synthesis of podands bearing a thiophen-2-yl substituent. Trace amounts of monosubstituted podands were also detected, containing a free hydroxy group along with the triazolodihydropyrimidine pharmacophore. |
Stereoselective synthesis of dihydropyrimidinethione podand in the presence of L-proline or 4-hydroxy-L-proline and metal nitrates / E. S. Filatova, O. V. Fedorova, I. G. Ovchinnikova [et al.] // Russian chemical bulletin. - 2022. - Vol. 71, № 7. - P1506-1513 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The asymmetric Biginelli reaction involving a 3-oxobutanoyl-containing podand, benzaldehyde, and thiourea was studied using secondary amines as a chiral inductor, Brönsted acid as a catalyst, and metal salts (especially metal nitrates) as an additive of asymmetric catalysis (AAC) was studied. The tuberculostatically active dihydropyrimidine-thione-containing podand was synthesized with an enantiomeric excess of 57% in the presence of 4-hydroxy-L-proline. In the presence of metal nitrates, the influence of the ionic radius of the cation on the enantioselective excess of the reaction under study was observed, which made it possible to propose a possible mechanism of chiral induction controlled by the complexing ability of the initial β-ketoester-containing podand with metal ions and coordination of the reagents in the transition states. |