α‐Amidoalkylations at Carbon

Zaugg, Harold E.; Martin, William B.

doi:10.1002/0471264180.or014.02

Cited by 11 publications

(17 citation statements)

References 281 publications

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“…To increase the efficiency of the condensation reaction, the effects of different catalyst were investigated ( Table 1, entries 1-15). Potassium tert-butoxide exhibited the best performance with used solvents and gave better yield, ( Table 1, entries [11][12][13][14][15]. Potassium carbonate and sodium acetate gave lower yields with other solvents, but gave better yield in ethanol as a solvent ( Table 1, entries 1 and 6).…”

Section: Effect Of Catalyst and Solventsmentioning

confidence: 99%

“…The original Biginelli reaction was carried out by refluxing a mixture of the three components such as ethyl acetoacetate, benzaldehyde and urea in presence of ethanol catalyzed by small amount of HCl which often result in poor to moderate yields of desired product [7]. The one pot Biginelli protocol for 3,4dihydropyrimidines synthesis was explored by varying all components and catalyst [8][9][10][11][12][13][14][15][16] in protic, aprotic solvents, and solvent free condition [17] using ether classical heating, microwave [18,19].…”

Section: Introductionmentioning

confidence: 99%

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Microwave assisted facile synthesis and anticancer evaluation of novel ethyl 4-(substituted phenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

Sarkate

Pansare

Tiwari³

et al. 2020

Proceedings of the 24th International Electronic Conference on Synthetic Organic Chemistry

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Herewith, we report the design and synthesis of a novel series of ethyl 4-(substituted phenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate derivatives, obtained by condensation of substituted aldehydes, ethyl 3-oxobutanoate and urea in ethanol as solvent and Potassium tert-butoxide as a catalyst under microwave irradiation for about 2-4 min (800 W) to get structural prerequisite indispensable for anticancer activity. The synthesized derivatives will be investigated for MTT assay, enzymatic assay and molecular modeling studies. Compounds were found to be potent in docking studies.

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Section: Effect Of Catalyst and Solventsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Microwave assisted facile synthesis and anticancer evaluation of novel ethyl 4-(substituted phenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

Sarkate

Pansare

Tiwari³

et al. 2020

Proceedings of the 24th International Electronic Conference on Synthetic Organic Chemistry

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“…The Biginelli reaction is a multiple-component chemical reaction that creates 3, 4-dihydropyrimidin-2(1H)ones 4 from ethyl acetoacetate 1, an aryl aldehyde (such as benzaldehyde 2), and urea 3. (Biginelli, 1891(Biginelli, , 1893Zaugg and Martin, 1965;Kappe, 1993) (Figure 1).…”

Section: Biginelli Reactionmentioning

confidence: 99%

Pyrimidine derivatives as environmentally-friendly corrosion inhibitors: A review

Loto¹

2012

Int. J. Phys. Sci.

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The perpetual quest for more efficient and environment friendly corrosion inhibitors remain a focal point in corrosion control. The use of organic compounds to inhibit corrosion has assumed great significance due to their vast applications in counteracting wastage of ferrous alloys. These compounds have shown great effectiveness for inhibiting aqueous corrosion due to film formation by adsorption on the metal surface. This paper reviews the inhibitive effect of pyrimidine derivatives as corrosion inhibitor. This class of heterocyclic aromatic organic compound has very important theoretical and practical applications. Their effect on the corrosion of metallic alloys was evaluated through assessment of various techniques and articles on their use in various investigations. The corrosion rate was found to be a function of different variables. Due attention was paid to the systematic study of inhibitor action of derivatives with much emphasis on the inhibitor type and functional groups of the molecular structure. The comprehensive discourse presented concludes, that the pyrimidine derivatives fulfill the basic requirements for consideration as an efficient corrosion inhibitor.

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“…1 N,N-Bis(phthalimidomethyl)trifluoromethanesulfonamide (VIIb). N-Hydroxymethylphthalimide, obtained by reacting the phthalimide with water solution of formaldehyde in the presence of potassium carbonate [8], was converted into N-chloromethylphthalimide (Vb) by the reaction with PCl 5 in chloroform by procedure [9]. To a solution of 0.96 g (5.6 mmol) of CF 3 SO 2 NHNa (VI) in 4 ml of DMF was added by small portions 1 g (5.1 mmol) of N-chloromethylenephthalimide, the mixture was stirred for 2 h at room temperature, 4 h at 80°C, 5 h at 110°C, and 5 h at 140°C, then it was poured on ice with NaCl, the separated precipitate was filtered off and recrystallized from acetone.…”

Section: Nn'-bis[(trifluoromethylsulfonyl)aminomethyl]-succinamide (mentioning

confidence: 99%

Reaction of γ-dicarboxylic acids amides and imides with trifluoromethanesulfonamide and formaldehyde

2009

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Three-component condensation of trifluoromethanesulfonamide with paraformaldehyde and succinamide depending on the reaction conditions led alongside bis(trifluoromethanesulfonamido)methane to the formation of a substitution product, bis[(trifluoromethylsulfonyl)aminomethyl]succinamide, or to a cyclization product, N-[trifluoromethylsulfonyl)aminomethyl]succinimide. The attempt to obtain the latter by the reaction of the trifluoromethanesulfonamide sodium salt CF 3 SO 2 NHNa with N-chloromethylsuccinimide unexpectedly resulted in N,N-bis(succinimidomethyl)-trifluoromethanesulfonamide. Analogously the reaction of CF 3 SO 2 NHNa with N-chloromethyl-phthalimide gave N,N-bis(phthalimidomethyl)trifluoromethanesulfonamide. The reaction of CF 3 SO 2 NHNa with succinimide and phthalimide in water and alcohol solution resulted in the ring opening and further transformation of the formed monosubstituted N-(trifluoromethylsulfonyl)amides of succinic and phthalic acids.We showed formerly that the condensation of trifluoromethanesulfonamide (triflamide) CF 3 SO 2 NH 2 with paraformaldehyde depending on the reaction conditions led to the formation of versatile linear and cyclic products [1,2]. Also the three-component reactions of triflamide with paraformaldehyde and various amides were investigated, and in some events mixed condensation products were obtained [3]. It was shown in particular that the reaction of triflamide, paraformaldehyde, and malonamide provided a spirocyclic condensation product involving both amido groups and the methylene group of the malonamide, 4,10-bis-(trifluoromethylsulfonyl)-2,4,8,10-tetraazaspiro-[5,5]undecane-1,7-dione [3]. In extension of this research the present study consists in the investigation of the reaction of succinamide, succinimide, and phthalimide with trifluoromethanesulfonamide and formaldehyde under various conditions.The investigation of the transformations in the system trifluoromethanesulfonamide-formaldehyde−succinamide (I) revealed the fundamental dependence of the reaction direction on its conditions. In the medium of concn. H 2 SO 4 alongside the unreacted triflamide and the linear product of its condensation with formaldehyde [bis(trifluoromethanesulfonamido)methane (II)] the formation was found of a product of the triple condensation at both amido groups, bis[(trifluoromethylsulfonyl)aminomethyl]-succinamide (III) that was isolated after washing the reaction product II with a mixture ether-hexane and was recrystallized from dichloromethane.The same reaction carried out in ethyl acetate in the presence of sulfuric acid alongside compound II unexpectedly furnished a cyclic amidomethylation product, N-[(trifluoromethylsulfonyl)aminomethyl]succinimide (IV) isolated analogously and recrystallized from chloroform.The structure of compound III was proved by the presence in its 1 H NMR spectrum of a singlet from CH 2 CH 2 group at 2.36 ppm, a broadened singlet of NHSO 2 , a triplrt of NHCO, and a doublet of NCH 2 N in the ratio 2:1:1:2, and of the corresponding signals in the 13 C...

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α‐Amidoalkylations at Carbon

Cited by 11 publications

References 281 publications

Microwave assisted facile synthesis and anticancer evaluation of novel ethyl 4-(substituted phenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

Microwave assisted facile synthesis and anticancer evaluation of novel ethyl 4-(substituted phenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

Pyrimidine derivatives as environmentally-friendly corrosion inhibitors: A review

Reaction of γ-dicarboxylic acids amides and imides with trifluoromethanesulfonamide and formaldehyde

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