- Transition-Metal-Free Synthesis of Pyrrolo[1,2- a ]pyrazines via Intramolecular Cyclization of N -Propargyl(pyrrolyl)enaminones
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A concise transition-metal-free strategy for the synthesis of pyrrolo[1,2- a ]pyrazines with enone substituents has been developed. It includes the following key steps: (a) cross-coupling of pyrroles with acyl(bromo)acetylenes in solid alumina at room temperature to give 2-(acylethynyl)pyrroles; (b) addition of propargylamine to the above acetylenes to form the corresponding N -propargylenaminones; and (c) chemo- and stereoselective base-catalyzed (Cs 2 CO 3 /DMSO) intramolecular cyclization of the synthesized propargylic derivatives to form (acylmethylidene)pyrrolo[1,2- a ]pyrazines of Z -configuration.
- Sobenina, Lyubov N.,Sagitova, Elena F.,Ushakov, Igor A.,Trofimov, Boris A.
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- Cross-coupling of 4,5,6,7-tetrahydroindole with functionalized haloacetylenes on active surfaces of metal oxides and salts
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Screening was performed of metal oxides (MgO, CaO, ZnO, BaO, Al 2O3, TiO2, ZrO2) and salts (CaCO3, K2CO3, ZrSiO4) as active surfaces for the reaction of ethynylation o
- Sobenina,Tomilin,Petrova,Gulia,Osowska,Szafert,Mikhaleva,Trofimov
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- Pyrrole–aminopyrimidine ensembles: Cycloaddition of guanidine to acylethynylpyrroles
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An efficient method for the synthesis of pharmaceutically prospective pyrrole–aminopyrimidine ensembles (in up to 91% yield) by the cyclocondensation of easily available acylethynylpyrroles with guanidine nitrate has been developed. The reaction proceeds
- Budaev, Arsalan B.,Ivanov, Andrey V.,Petrova, Olga V.,Sagitova, Elena F.,Sobenina, Lyubov N.,Trofimov, Boris A.,Ushakov, Igor A.
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- Functionalized Bipyrroles and Pyrrolyl-Aminopyrones from Acylethynylpyrroles and Diethyl Aminomalonate
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An efficient method for the synthesis of 1H,1?H-2,3?-bipyrroles (up to 72% yield) by the cyclocondensation of easily available 2-(acylethynyl)pyrroles with diethyl aminomalonate hydrochloride has been developed. The reaction proceeds under reflux in MeCN
- Gotsko, Maxim D.,Kireeva, Victoriya V.,Saliy, Ivan V.,Sobenina, Lyubov N.,Trofimov, Boris A.,Ushakov, Igor A.
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- Peculiarities of the cascade cleavage of the polarized C - C-fragment in α-ketoacetylenes on reaction with ethylene diamine
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The reaction of diarylketoacetylenes with ethylenediamine (EDA) leads to arylmethylketones and 2-substituted imidazoline derivatives. This transformation involves complete cleavage of the triple bond via initial intermolecular Michael-addition with subsequent intramolecular Michaeladdition. Final fragmentation can be presented as a retro-Mannich reaction, accompanied by three formal reductive stages (formation of three C-H bonds), while the other carbon undergoes a formal oxidation, in which three C-N bonds (C-N and C=N) are formed. ARKAT-USA, Inc.
- Vasilevsky, Sergei F.,Davydova, Maria P.,Tomilin, Denis N.,Sobenina, Lyubov N.,Mamatuyk, Victor I.,Pleshkova, Nadezhda V.
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p. 132 - 144
(2014/08/18)
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- From 4,5,6,7-tetrahydroindoles to 3- or 5-(4,5,6,7-tetrahydroindol-2-yl) isoxazoles in two steps: A regioselective switch between 3- and 5-isomers
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(4,5,6,7-Tetrahydroindol-2-yl)alkynes, synthesized by cross-coupling of 4,5,6,7-tetrahydroindoles with aroyl(hetaroyl)bromoalkynes or ethyl bromopropynoate in the presence of K2CO3, regioselectively cyclize with hydroxylamine to eith
- Sobenina, Lyubov N.,Tomilin, Denis N.,Gotsko, Maxim D.,Ushakov, Igor A.,Mikhaleva, Albina I.,Trofimov, Boris A.
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p. 5168 - 5174
(2014/07/08)
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