- Reductive CO2Fixation via the Selective Formation of C-C Bonds: Bridging Enaminones and Synthesis of 1,4-Dihydropyridines
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Herein, a selective tandem C-C bond-forming reaction with CO2 was developed to realize the bridging of enaminones and synthesis of 1,4-dihydropyridines, respectively. n-Butylamine significantly promoted this CO2 deoxymethylenation procedure catalyzed by 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) and ZnCl2. The mechanism involving the formation of bis(silyl)acetal, nucleophilic addition, and amine elimination was also interpreted to clarify the bridging of two molecules of enaminones with CO2 and the generation of dihydropyridine derivatives.
- Zhao, Yulei,Guo, Xuqiang,Ding, Xin,Zhou, Zheng,Li, Man,Feng, Nan,Gao, Bowen,Lu, Xu,Liu, Yunlin,You, Jinmao
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supporting information
p. 8326 - 8331
(2020/11/03)
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- Synthesis of 9-R1-10-R-1,8-dioxo-decahydroacridines and dioximes based on them
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3,3,6,6-Tetramethyl-9-R1-10-R-1,8- dioxo-1,2,3,4,5,6,7,8,9,10-decahydroacridines were synthesized through the intermediate α-R-methylenebisenamino ketones by the condensation of 5,5-dimethyl-3-N-R-aminocyclohex-2-enones with aliphatic, aromatic, and furan aldehydes (2-propanol, phosphorus pentoxide). It was found that the degree of substitution of the heterocycle in decahydroacridinediones has an effect on the direction of their transformations during oximation.
- Shchekotikhin,Getmanenko,Nikolaeva,Kriven'ko
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p. 1228 - 1233
(2007/10/03)
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- Peculiarities of formation of decahydroacridine-1,8-diones on the basis of 1,3-dioxocyclohexane compounds in various media
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The conditions for the formation of N-substituted decahydroacridine-1,8-diones from α-R-methylenebiscyclohexane-1,3-diones and 5,5-dimethyl-3-(N-methylamino)-2-cyclohexen-1-one in ethanol, isopropanol, and DMSO have been studied. Methods have been develop
- Nikolaeva,Shchekotikhin,Ponomarev,Kriven'ko
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p. 403 - 409
(2007/10/03)
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- Synthesis, characterization, and electrochemistry of some acridine-1,8-dione dyes
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The synthesis, characterization, and electrochemical behavior of some acridinedione derivatives are reported. Cyclic voltammetric studies show that all the dyes undergo irreversible oxidation irrespective of the substitution on the nitrogen. The product formed on oxidation is the aromatic derivative in the case of N-H compounds and the acridinium salt in the case of the N-substituted compounds, which have been isolated and characterized. Formation of an intermediate carbon-centered radical is observed as evidenced by ESR spin-trapping experiments. A mechanistic scheme for the electrochemical oxidation is proposed. On carrying out reduction after oxidation, different products are formed depending on the substitution on the nitrogen. There is no reduction of the oxidized product in the case of N-H compounds, and compounds with substitution on nitrogen undergo reduction consistent with the observation in N-alkylpyridinium salts.
- Srividya,Ramamurthy,Shanmugasundaram,Ramakrishnan
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p. 5083 - 5089
(2007/10/03)
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- UREAS IN ORGANIC SYNTHESIS VIII. SYNTHESIS OF HYDROGENATED 10-ARYLACRIDINE-1,8-DIONES BY THE REACTION OF 5,5-DIMETHYLCYCLOHEXANE-1,3-DIONE WITH DIARYLUREAS OR ANILINES IN FORMIC ACID
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The reaction of dimedone with diarylureas or anilines in formic acid were studied.As a result the hydrogenated 10-arylacridine-1,8-diones were formed with satisfactory yields.It was established that the reaction of dimedone with diphenylurea and benzaldehydes in formic acid leads exclusively to 9,10-diaryl-substituted acridine-1,8-diones.
- Bakibaev, A. A.
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p. 1109 - 1112
(2007/10/02)
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- Raection of dimedone enamines with α-ketoacids
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Reaction of enaminoketones (1), derived from dimedone, with pyruvic acid gave the lactams (2) and (3).Compounds (2) were dehydrated to (3) with acetic anhydride.In the case of (2j), two diastereoisomers were isolated due to restricted rotation of the N-ar
- Viswanathan, Narayanaiyer,Rawle, Ninad Namdeo,Gawad, Dilip Harischandra
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p. 2760 - 2773
(2007/10/02)
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- CYCLIZATION OF PRIMARY AROMATIC AMINES WITH FORMALDEHYDE AND DIMEDONE IN THE PRESENCE OF PERCHLORC ACID
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In reaction with formaldehyde nad dimedone and also with bis(2-hydroxy-6-oxo-4,4-dimethyl-1-cyclohexenyl)methane in the presence of perchloric acid primary aromatic amines form mixtures of 1,8-dioxo-3,3,6,6-tetramethyl-10-aryl-1,2,3,4,5,6,7,8,9,10-decahyd
- Mel'nik, M. V.,Kornilov, M. Yu.,Turov, A. V.,Gutsulyak, B. M.
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p. 1272 - 1277
(2007/10/02)
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