A Simple Method for the Synthesis of Carbamates

Ángeles, Enrique; Santillan, A.; Martı́nez, Ignacio; Ramírez, Aldo Bazán; Moreno, Enrique Martínez; Salmón, Manuel; Martı́nez, Roberto

doi:10.1080/00397919408010552

Cited by 28 publications

(13 citation statements)

References 23 publications

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“…Because of their importance, the synthesis of carbamates has become a focus of synthetic organic chemistry and several efforts have been made for the preparation of the title compounds. Initially carbamates were almost exclusively synthesized by the reaction of amines with phosgene or its derivatives such as chloroformate, [2a,3] dialkyl carbonates [4] or reaction of alcohols with isocyanates. [5] These procedures had several drawbacks, notably the extreme toxicity of reagents and generation of by-products.…”

mentioning

confidence: 99%

Copper‐Catalyzed Coupling of Arylboronic Acids with Potassium Cyanate: A New Approach to the Synthesis of Aryl Carbamates

Kianmehr

Baghersad

2011

Adv Synth Catal

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confidence: 99%

Copper‐Catalyzed Coupling of Arylboronic Acids with Potassium Cyanate: A New Approach to the Synthesis of Aryl Carbamates

Kianmehr

Baghersad

2011

Adv Synth Catal

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“…Synthetic ethyl and methyl phenylcarbamates are used, for example, as pesticides and insecticides (2). According to their chemical structures and theoretical studies of their qualitative structure-activity relationships, some of these compounds have FIG.…”

Section: Discussionmentioning

confidence: 99%

“…Carbamic acid derivatives (Table 1) were synthesized by the method described by Angeles et al (2). Briefly, aryl-and alkyl-amines with sodium hydride and diethylcarbonate were used in dry benzene as the solvent; they were then purified by column chromatography and recrystallized.…”

Section: Methodsmentioning

confidence: 99%

Antiamoebic and Toxicity Studies of a Carbamic Acid Derivative and Its Therapeutic Effect in a Hamster Model of Hepatic Amoebiasis

Ordaz-Pichardo¹,

Shibayama

Villa‐Treviño³

et al. 2005

Antimicrob Agents Chemother

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Amoebiasis is an important public health problem in developing countries. Entamoeba histolytica, the causative agent of amoebiasis, may develop resistance to nitroimidazoles, a group of drugs considered to be the most effective against this parasitic disease. Therefore, research on new drugs for the treatment of this common infection still constitutes an important therapeutic demand. In the present study we determined the effects of a carbamate derivative, ethyl 4-chlorophenylcarbamate (C4), on trophozoites of E. histolytica strain HM-1: IMSS. C4 was subject to various toxicity tests, including the determination of mutagenicity for bacterial DNA and changes in the enzymatic activities of eukaryotic cells. Genotoxicity studies were performed by the mutagenicity Ames test (plate incorporation and preincubation methods) with Salmonella enterica serovar Typhimurium, with or without metabolic activation produced by the S9 fraction of rat liver. C4 toxicity studies were performed by measuring enzymatic activity in eukaryotic cells by the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide-formazan test with Fischer 344 rat hepatocytes. C4 did not induce either frameshift mutations in S. enterica serovar Typhimurium TA97 or TA98 or base pair substitutions in strains TA100 and TA102. The compound was not toxic for cultured rat hepatic cells. Trophozoites treated with 100 g of C4 per ml were inhibited 97.88% at 48 h of culture; moreover, damage to the amoebae was also confirmed by electron microscopy. The antiamoebic activity of C4 was evaluated by using an in vivo model of amoebic liver abscess in hamsters. Doses of 75 and 100 mg/100 g of body weight reduced the extent of the amoebic liver abscess by 84 and 94%, respectively. These results justify further studies to clearly validate whether C4 is a new suitable antiamoebic drug.

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“…They may react with aliphatic amines undergoing an attack at the carbonyl carbon atom, followed by ring opening to produce urethanes [257] which, in the absence of amines and upon loss of water, generate oxazolidinones. The latter may react in the presence of an excess of amines to afford imidazolidinones [258] (Scheme 7.16 ).…”

Section: Reactivity Of Cyclic Alkylene Carbonatesmentioning

confidence: 99%