A New Simple One-Pot Regioselective Preparation of Mixed Diesters of Carbonic Acid

Bertolini, Giorgio; Pavich, Gianfranco; Vergani, Barbara

doi:10.1021/jo980286e

Cited by 34 publications

(22 citation statements)

References 12 publications

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“…As shown in Scheme , the synthesis of novel piperidin‐4‐one oxime carbamates containing different substituents ( 5a–5k ) was adopted a four‐step synthetic protocol. The oxime ( 4 ) was synthesized through Mannich condensation of benzaldehyde, methyl propyl ketone, and ammonium acetate in 2:1:1 ratio, followed by methylation and oximation, respectively . From the initial feasibility test of oxime carbamate formation in the presence of sodium hydride as base, THF yielded the best result compared to other solvents, such as dimethylformamide, acetonitrile, dichloromethane, and 1,4‐dioxane.…”

Section: Resultsmentioning

confidence: 99%

“…To further optimize the reaction condition, we produced one of the piperidin‐4‐one oxime carbamate ( 5a ) via two different intermediates (Scheme ), such as oxime–imidazolide and amine–imidazolide, respectively. The reaction of alcohol with CDI is well known to give an imidazolide intermediate with the release of 1 equiv of imidazole . Similarly, the oxime ( 4 ) reacted with CDI to form the oxime–imidazolide intermediate (Scheme , 4a ).…”

Section: Resultsmentioning

confidence: 99%

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Synthesis of Secondary and Tertiary Oxime Carbamate Derivatives and their Structure‐Dependent Bioactivity

Sivakumar

Thanikachalam

Kim

et al. 2017

Bulletin Korean Chem Soc

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Biologically active novel piperidin‐4‐one oxime carbamates were synthesized from 3‐ethyl‐1‐methyl‐2,6‐diphenylpiperidin‐4‐one oxime, 1,1′‐carbonyldiimidazole (CDI), and primary or secondary amines in the presence of sodium hydride as base. Commercially available, cheaper, and safer CDI was utilized as carbonyl source, instead of toxic phosgene/triphosgene and carbon monoxide. The devised method is feasible for primary and secondary amines to make their corresponding oxime carbamate derivatives, through oxime–imidazolide intermediate, in high yield. When the antimicrobial activity of obtained oxime carbamate derivatives was investigated in comparison with streptomycin and amphotericin B as standards, the oxime carbamate containing heteroaromatic thiazole ring exhibits outstanding antimicrobial effectiveness, regardless of bacterial or fungal types.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Synthesis of Secondary and Tertiary Oxime Carbamate Derivatives and their Structure‐Dependent Bioactivity

Sivakumar

Thanikachalam

Kim

et al. 2017

Bulletin Korean Chem Soc

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“…To demonstrate the advantage of 6 for the parallel protection of amines, it was transformed into the carbamate 10, which readily reacted with primary amines such as furfurylamine or benzylamine after addition of catalytic amounts of 4-(dimethylamino)pyridine (DMAP) (Scheme 3) [13]. For the protection of less nucleophilic or secondary amines, 10 had to be activated via N-methylation using methyl trifluoromethane sulfonate (MeOTf).…”

Section: Methodsmentioning

confidence: 99%

Perfluoro-Tagged Benzyloxycarbonyl Protecting Group and Its Application in Fluorous Biphasic Systems

Schwinn

Bannwarth

2002

HCA

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The synthesis of a new perfluoro‐tagged benzyloxycarbonyl protecting group is reported, as well as its application in the parallel protection of amines. Isolation of the protected amines was performed by simple liquid‐liquid extraction between perfluorinated and organic solvents. Deprotection was achieved by standard hydrogenolysis. The novel protecting group was also applied to cyclization protocols leading to quinazoline‐2,4‐diones. These products were isolated by simple extraction procedures

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“…The spectral features are reported in wave number (cm -1 ). 1 H NMR spectra were recorded on a Bruker 400 MHz spectrometer and 13 C NMR spectra were recorded on a Bruker 100 MHz spectrometer at Annamalai University, International Letters of Chemistry, Physics and Astronomy Vol. 6631+G(d, p).…”

Section: Spectral Measurementsmentioning

confidence: 99%

“…Synthesis of linear carbonates mainly makes use phosgene and its derivatives [11][12][13][14] as the starting material, while cyclic carbonates are synthesized from propylene oxide. As an alternative approach, substituted chloroformates [15][16][17] are the most frequently used reagents for the preparation of organic carbonates.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Spectroscopic Investigation and Computational Studies of 2-Formyl-4-(Phenyldiazenyl)Phenyl Methyl Carbonate and 4-((4-Chlorophenyl)Diazenyl)-2-Formylphenyl Methyl Carbonate

Arokiasamy

Manikandan

Thanikachalam

et al. 2016

ILCPA

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ABSTRACT. Two new compounds namely 2-formyl-4-(phenyldiazenyl)phenyl methyl carbonate (FPMC) and 4-((4-chlorophenyl) diazenyl)-2-formylphenyl methyl carbonate (CFPMC) have been synthesized and have characterized using FT-IR, FT-Raman, 1 H and 13 C NMR techniques. Computational optimization studies have been carried out using Hatree-Fock (HF) and Density Functional Theory (DFT-B3LYP) methods with 6-31+G(d, p) basis set of Gaussian 09W software. The stable configuration of the title compounds were achieved theoretically by potential energy surface scan analysis. The complete vibrational assignments were performed on the basis of total energy distribution (TED) and natural bonding orbital (NBO) have been studied. Various parameters such as E HOMO , E LUMO , total energy, dipole moment, polarizability, first order hyperpolarizability, zero-point vibrational energy as well as thermal properties were analyzed and reported for the title compounds.

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A New Simple One-Pot Regioselective Preparation of Mixed Diesters of Carbonic Acid

Cited by 34 publications

References 12 publications

Synthesis of Secondary and Tertiary Oxime Carbamate Derivatives and their Structure‐Dependent Bioactivity

Synthesis of Secondary and Tertiary Oxime Carbamate Derivatives and their Structure‐Dependent Bioactivity

Perfluoro-Tagged Benzyloxycarbonyl Protecting Group and Its Application in Fluorous Biphasic Systems

Synthesis, Spectroscopic Investigation and Computational Studies of 2-Formyl-4-(Phenyldiazenyl)Phenyl Methyl Carbonate and 4-((4-Chlorophenyl)Diazenyl)-2-Formylphenyl Methyl Carbonate

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