61985-23-7

Usage

Uses

1. Used in Pharmaceutical Synthesis:
1H-Imidazole-1-carboxylic acid, methyl ester (9CI) is used as a reagent for the amidation and esterification of carboxylic acids in the pharmaceutical industry. Its chemoselective nature allows for the synthesis of specific compounds with minimal side reactions, which is crucial for the development of new drugs and therapeutic agents.
2. Used in the Synthesis of Fluorinated L-Carbidopa Derivatives:
In the field of medicinal chemistry, 1H-Imidazole-1-carboxylic acid, methyl ester (9CI) is used as a precursor to prepare fluorous β-keto esters. These fluorous β-keto esters are essential for the synthesis of fluorinated L-carbidopa derivatives, which have potential applications in the treatment of Parkinson's disease and other related conditions.
3. Used in Organic Chemistry Research:
1H-Imidazole-1-carboxylic acid, methyl ester (9CI) is also utilized in organic chemistry research for the study of various reaction mechanisms and the development of new synthetic methods. Its unique reactivity and structural features make it a valuable tool for chemists working on the design and synthesis of complex organic molecules.

Upstream product

• 288-32-4 1H-imidazole 
• 79-22-1 methyl chloroformate 
• 67-56-1 methanol 
• 530-62-1 1,1'-carbonyldiimidazole 
• 1848-01-7 4-methylphenyl methyl carbonate 

Downstream Products

• 64464-76-2 methyl 2-phenyl-2-(phenylamino)acetate 
• 125990-08-1 methyl α-(p-methoxyphenylamino)-α-phenylacetate 
• 141693-19-8 methyl (+/-)-4-methoxy-2-oxo-3-cyclopentene-1-carboxylate 
• 138495-02-0 methyl 2-(4-chlorophenyl)-2-((4-methoxyphenyl)amino)acetate 
• 62013-44-9 methyl 2-nitro-propionate 
• 93-58-3 benzoic acid methyl ester 
• 119-61-9 benzophenone 
• 76-84-6 triphenylmethyl alcohol 
• 83395-25-9 methyl 7-<3,6-dihydro-1(2H)-pyridyl>-2-oxo-2H-<1,2,4>-oxadiazolo<2,3-c>pyrimidine-5-carbamate 
• 53525-65-8 5H,10H-diimidazo[1,5-a:1,5-d]pyrazine-5,10-dione 
• 79711-73-2 diimidazo<3,2-a:3',2'-d>pyrazine-5,10-dione 
• 99560-60-8 diimidazo<3,2-a:3',4'-d>pyrazine-5,10-dione 
• 89-71-4 2-Methyl-benzoic acid methyl ester 
• 31954-27-5 N-(tert-butoxycarbonyl)glycine methyl ester 

Relevant academic research and scientific papers

Facile access to imidazole derivatives: Carboxylic acids and δ-lactones

The nucleophilic addition of bis-(TMS)ketene acetals to doubly N-activated imidazole under mild conditions, leads to their corresponding dihydroimidazolyl carboxylic acids in a first instance. Subsequent reaction of these acids can be efficiently turned i

Palladium-Catalyzed Oxidative C–H Alkoxycarbonylation of Arenes with Alkylcarbazates Directed by N-Heterocyclic Substituents

With alkyl carbazates as the green ester source, a novel palladium-catalyzed oxidative free radical carbonylative transformation of the C–H bond on aromatic rings to produce esters has been developed. Good yields of the corresponding products have been obtained with wide functional group tolerance and excellent regioselectivity. A variety of alkyl carbazates are found to be suitable reactants for the ortho-alkoxycarbonylation on the aromatic ring.

Enantioselective Syntheses of Strychnos and Chelidonium Alkaloids through Regio- and Stereocontrolled Cooperative Catalysis

We describe enantioselective syntheses of strychnos and chelidonium alkaloids. In the first case, indole acetic acid esters were established as excellent partner nucleophiles for enantioselective cooperative isothiourea/Pd catalyzed α-alkylation. This provides products containing indole-bearing stereocenters in high yield and with excellent levels of enantioinduction in a manner that is notably independent of the N-substituent. This led to concise syntheses of (?)-akuammicine and (?)-strychnine. In the second case, the poor performance of ortho-substituted cinnamyl electrophiles in the enantioselective cooperative isothiourea/Ir catalyzed α-alkylation was overcome by appropriate substituent choice, leading to enantioselective syntheses of (+)-chelidonine, (+)-norchelidonine, and (+)-chelamine.

One-pot protection-glycosylation reactions for synthesis of lipid II analogues

(2,6-Dichloro-4-methoxyphenyl)(2,4-dichlorophenyl)methyl trichloroacetimidate (3) and its polymer-supported reagent 4 can be successfully applied to a one-pot protection-glycosylation reaction to form the disaccharide derivative 7 d for the synthesis of lipid II analogues. The temporary protecting group or linker at the C-6 position and N-Troc protecting group of 7 d can be cleaved simultaneously through a reductive condition. Overall yields of syntheses of lipid II (1) and neryl-lipid II Nε-dansylthiourea are significantly improved by using the described methods. Sweet synthetic methods: A one-pot protection glycosylation reaction of the diol glycosyl acceptor is developed for synthesis of the lipid II disaccharide (see figure, Troc=2,2,2-trichloroethoxycarbonyl). Improved syntheses of lipid II and neryl-lipid II analogues are summarized.

Palladium-catalyzed C3-benzylation of indoles

A general method for regioselective C3-benzylation of indoles has been developed. Various 3-substituted indoles and benzyl methyl carbonates with different electronic properties react under mild conditions to afford a diverse range of 3-benzylindolenine products in good yields.

On the reactivity of imidazole carbamates and ureas and their use as esterification and amidation reagents

The optimization, substrate scope, and mechanism of esterification and amidation of carboxylic acids mediated by imidazole-based reagents are discussed. The innate reactivity of carbonylimidazole reagents with a range of nucleophiles is also explored. New reagents developed for the synthesis of α,β-unsaturated esters are described, as are reagents for the preparation of tertiary amides directly from carboxylic acids.

Chemoselective esterification and amidation of carboxylic acids with imidazole carbamates and ureas

Imidazole carbamates and ureas were found to be chemoselective esterification and amidation reagents. A wide variety of carboxylic acids were converted to their ester or amide analogues by a simple synthetic procedure in high yields.

Direct N-carbamoylation of 3-monosubstituted oxindoles with alkyl imidazole carboxylates

(Chemical Equation Presented) Regioselective N-carbamoylation of oxindoles was achieved through the use of imidazole carboxylate reagents. This reaction provides ready access to N-carbamoyl-3-monosubstituted oxindoles.

Electroreductive acylation of aromatic imines with acylimidazoles

The intermolecular reductive coupling of aromatic imines with acylimidazoles was effected by electroreduction in the presence of chlorotrimethylsilane and gave α-amino-α-aryl ketones. This method was also effective for the synthesis of α-amino-α-aryl esters using methoxycarbonylimidazole as an electrophile.

Electroreductive acylation of aromatic ketones with acylimidazoles

The intermolecular reductive coupling of aromatic ketones with acylimidazoles was effected by electroreduction in the presence of chlorotrimethylsilane and gave α-trimethylsiloxy ketones and esters. The best result was obtained using Bu4NPF6 as a supporting electrolyte and a Pb cathode in THF. The α-trimethylsiloxy-containing products were transformed to the corresponding α-hydroxy ketones and esters by treatment with TBAF in THF. This method was also effective for the intramolecular reductive coupling of δ- and ε-keto acylimidazoles.