52122-98-2

Usage

Derivative of imidazole

The compound is based on the imidazole structure, which is a five-membered heterocyclic ring containing three carbon atoms and two nitrogen atoms.

Ester

The compound contains a carbonyl group (C=O) bonded to an oxygen atom (O), indicating the presence of an ester functional group.

Two methyl groups

The imidazole ring in the compound has two methyl (CH3) groups attached to it, which can affect its reactivity and physical properties.

Used in synthesis

The compound is used as a building block or intermediate in the synthesis of various pharmaceuticals, agrochemicals, and other organic compounds due to its versatile reactivity and biological activity.

Upstream product

• 67-56-1 methanol 
• 888-60-8 2-phenyl-1H-imidazole-4,5-dicarboxylic acid 
• 1097966-68-1 5-(methoxycarbonyl)-2-phenyl-1H-imidazole-4-carboxylic acid 
• 154546-41-5 (Z)-2-Benzylamino-but-2-enedioic acid dimethyl ester 
• 762-42-5 dimethyl acetylenedicarboxylate 
• 100-46-9 benzylamine 
• 586966-04-3 dimethyl (E/Z)-2-(5-phenyltetrazol-1-yl)butenedioate 

Downstream Products

• 117120-97-5 dimethyl 1-methyl-2-phenyl-1H-imidazole-4,5-dicarboxylate 
• 117121-04-7 (5-Hydroxymethyl-3-methyl-2-phenyl-3H-imidazol-4-yl)-methanol 
• 117120-87-3 Methyl-carbamic acid 3-methyl-5-methylcarbamoyloxymethyl-2-phenyl-3H-imidazol-4-ylmethyl ester 
• 851772-88-8 C₁₃H₁₃N₃O₄ 

Relevant academic research and scientific papers

Photocatalytic Visible-Light-Induced Nitrogen Insertion via Dual C(sp3)-H and C(sp2)-H Bond Functionalization: Access to Privileged Imidazole-based Scaffolds

Here we have demonstrated a visible-light-mediated metal-free organic-dye-catalyzed dehydrogenative N-insertion leading to highly substituted imidazoles and privileged dihydroisoquinoline-based imidazole derivatives via C(sp3)-H and C(sp2)-H bond functionalization. A sustainable, convenient, metal-free azidation/C-H aminative cyclization approach in the absence of stoichiometric oxidants is presented. This protocol involves a rare photoinduced iminyl radical as a key intermediate for the "N"insertion.

Design and synthesis of optically active 2-phenylimidazolecarboxamides featuring amino acid motive

(Chemical Equation Presented) Overall sixteen new, optically active carboxamides 1-3 have been synthesized. These compounds based on the 2-phenylimidazole and featuring amino acid residues are linked on the 4-position by an amidic bond. Two general methods were used for their construction. Whereas the first method employs acylchlorides as a reactive species, the second one involves a condensation of mixed anhydrides with the amino acid counterparts. Actually, the second method proved to be more efficient than the first one. Carboxamides 1-3 were preliminarily tested as N-chelating ligands with an application in the Henry or Aldol reactions affording either poor yields or enantiomeric excesses.

PHENYL-ANILINE SUBSTITUTED BICYCLIC COMPOUNDS USEFUL AS KINASE INHIBITORS

Compounds having the formula (I), and pharmaceutically acceptable salts, prodrugs, and solvates thereof, are useful as kinase inhibitors, wherein R, R1 , R2, R5, R6a, R6b, J, K, X and Z are as described in the specification.

The photochemistry of α-azidocinnamates - A reinvestigation

α-Azidocinnamates have been reported elsewhere to yield one diastereomer of a trimer in a stepwise and efficient manner by photolysis using quartz equipment. We find that use of pyrex filters or ketone sensitisation instead of quartz leads to high yields of the presumed intermediate diastereomeric pair of aziridinoimidazoline dimers, as does brief irradiation in quartz. These dimers have been characterised by spectral and crystallographic methods, and shown to oxidise with DDQ to give imidazoledicarboxylic esters, while the action of base on both dimer diastereomers leads to one rearranged dimer, a 1,2-dihydropyrimidine. Surprisingly, only a mixture of both diastereomeric dimers gives the trimer on further photolysis.

Design, Synthesis, Antineoplastic Activity, and Chemical Properties of Bis(carbamate) Derivatives of 4,5-Bis(hydroxymethyl)imidazole

A series of bis(carbamate) derivatives of 1,2-substituted 4,5-bis(hydroxymethyl)imidazoles were prepared and evaluated against murine P388 lymphocytic leukemia.Electron-withdrawing substituents at either N-1 or C-2 gave rise to inactive compounds.However, electron-donating substituents gave active compounds and the 2-(methylthio)-1-methyl derivative 2i (carmethizole), as the bis(N-methylcarbamate), was found to be very active.The derivative 2i, referred to by the name carmethizole, was also shown to be active against the MX-1 mammary xenograft, the human amelanotic melanoma cell line (LOX) xenograft, the M5076 sarcoma, and L1210 lymphocytic leukemia.The solution stability, water solubility, pKa, and log P of carmethizole are also reported.

Two-step Synthesis of Imidazoles from Activated Alkynes

Conjugate addition of 2-(tri-n-butylstannyl)tetrazoles (1) to activated alkynes gives 1-alkenyltetrazoles (4) and (5) predominantly.Use of the N-tributylstannyl derivatives, rather than the parent tetrazole, gives a high ratio of 1- to 2-alkenyl isomers and avoids the complication of further addition of the tetrazole or the alkyne to the initial adduct.Irradiation of the (Z)- and (E)-1-alkenyltetrazoles (4) and (5) at 254 nm then gives the expected imidazoles in moderate yield.However, 5-phenyl-2-(tri-n-butylstannyl)tetrazole (1a) reacted only slowly with ethyl phenylpropiolate to give ethyl 3,5-diphenylpyrazole-4-carboxylate (8), presumably via the 2-alkenyltetrazole (9) formed in preference to the 1-isomer for steric reasons.