Zolimidine

CAS

1222-57-7

Catalog Number

ACM1222577

Category

Main Products

Molecular Weight

Molecular Formula

C₁₄H₁₂N₂O₂S

MSDS COA Spec Sheet

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Specification

Synonyms

zolimidine;2-(4-Methylsulphonyl)phenyl]imidazo(1,2,a)pyridine;2-(p-Methylsulfonylphenyl)imidazo[1,2-a]pyridine;2-[4-(Methylsulfonyl)phenyl]imidazo[1,2-a]pyridine;Solimidin;Zolimidin;Zoliridine;2-(4-mesylphenyl)imidazo[1,2-a]pyridine

IUPAC Name

2-(4-methylsulfonylphenyl)imidazo[1,2-a]pyridine

InChI Key

VSLIUWLPFRVCDL-UHFFFAOYSA-N

Density

1.31 g/cm³

Exact Mass

272.06200

H-Bond Acceptor

H-Bond Donor

One-Step Synthesis of Zolimidine via an Ortoleva-King Type Reaction Catalyzed by Iron/Iodine

Ujwaldev, Sankuviruthiyil Mohanan, et al. Tetrahedron Letters, 2019, 60(33), 150950.

Imidazo[1,2-α]pyridines are nitrogen-bridged heterocyclic compounds containing an imidazole ring fused to a pyridine moiety, which have a wide range of pharmacological properties, such as Zolimidine (treatment of peptic ulcers). This work reports the first iron-catalyzed Ortoleva-King type synthesis of imidazo[1,2-α]pyridine in the presence of a catalytic amount of molecular iodine. It involves the one-step synthesis of Zolimidine via an Ortoleva-King type reaction catalyzed by iron iodide.
One-step synthesis strategy of Zolimidine
· To initiate the study, 0.60 mmol of 4-Methylpyridin-2-amine 1a and 0.50 mmol of acetophenone 2a were chosen as the model substrates. The initial reaction took place in acetonitrile at 80 °C in a sealed tube with 20 mol% of anhydrous FeCl3 serving as the catalyst and KI (20 mol%) as the source of iodine.
· Substrate scope studies were performed after a series of reaction condition optimizations. The optimal conditions were that the iodide source was I2, the solvent was chlorobenzene, the atmosphere was air, the temperature was 110 °C, and the reaction time was 62h.
· The possible application of this method in the pharmaceutical industry was later evaluated by attempting to directly synthesize the gastroprotective drug Zolimidine. It was found that under the optimized conditions, 2-aminopyridine (1b) and 1-(4-(methylsulfonyl)phenyl)ethanone reacted to produce the desired drug in 65% yield within 3 seconds.

What is the molecular formula of Zolimidine?

The molecular formula of Zolimidine is C14H12N2O2S.

What is the molecular weight of Zolimidine?

The molecular weight of Zolimidine is 272.32 g/mol.

What is the IUPAC name of Zolimidine?

The IUPAC name of Zolimidine is 2-(4-methylsulfonylphenyl)imidazo[1,2-a]pyridine.

What is the InChI of Zolimidine?

The InChI of Zolimidine is InChI=1S/C14H12N2O2S/c1-19(17,18)12-7-5-11(6-8-12)13-10-16-9-3-2-4-14(16)15-13/h2-10H,1H3.

What is the InChIKey of Zolimidine?

The InChIKey of Zolimidine is VSLIUWLPFRVCDL-UHFFFAOYSA-N.

What is the canonical SMILES of Zolimidine?

The canonical SMILES of Zolimidine is CS(=O)(=O)C1=CC=C(C=C1)C2=CN3C=CC=CC3=N2.