5000-95-3

Basic information

• Product Name: 3-(methylthio)-2-phenylimidazo[1,2-α]pyridine
• Synonyms: 3-(methylthio)-2-phenylimidazo[1,2-α]pyridine
• CAS NO: 5000-95-3
• Molecular Weight: 240.329
• Mol File: 5000-95-3.mol
• Article Data: 16

Chemical Properties

• CAS DataBase Reference: 3-(methylthio)-2-phenylimidazo[1,2-α]pyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(methylthio)-2-phenylimidazo[1,2-α]pyridine(5000-95-3)
• EPA Substance Registry System: 3-(methylthio)-2-phenylimidazo[1,2-α]pyridine(5000-95-3)

Safety Data

• Hazardous Substances Data: 5000-95-3(Hazardous Substances Data)

Upstream product

• 2949-92-0 methanethiosulfonic acid S-methyl ester 
• 4105-21-9 2-phenylimidazo[1,2-a]pyridine 
• 110-86-1 pyridine 
• 26060-56-0 (1-phenylethylidene)(benzoyloxy)amine 
• 67-68-5 dimethyl sulfoxide 
• 124-63-0 methanesulfonyl chloride 
• 504-29-0 2-aminopyridine 
• 536-74-3 phenylacetylene 
• 67-56-1 methanol 
• 74-88-4 methyl iodide 
• 4636-16-2 iodoacetophenone 
• 98-86-2 acetophenone 
• 20277-69-4 sodium methansulfinate 
• 10393-86-9 methanesulphonyl hydrazide 

Relevant articles and documents

Molecular iodine enabled generation of iminyl radicals from oximes: A facile route to imidazo[1,2-a]pyridines and its regioselective C-3 sulfenylated products from simple pyridines

An iodine promoted simple and environment friendly protocol has been developed to access imidazo[1,2-a]pyridines from unfunctionalized pyridines and oxime esters. This straightforward method efficiently converts the substrates into corresponding products affording moderate to good yields with large functional group tolerance. Additionally extensive investigation revealed that regioselective domino C-3 methyl sulfenylated imidazo[1,2-a]pyridines were also accessible first time from pyridines and oxime esters in DMSO solvent. The reaction operates through metal-free generation of iminyl radicals from easily accessible oxime esters, to build up the second heterocyclic ring on pyridines.

Electrochemical-induced regioselective C-3 thiomethylation of imidazopyridines: Via a three-component cross-coupling strategy

The electrochemical-induced regioselective C-3 thiomethylation of imidazopyridines has been initially accomplished via a three-component cross-coupling strategy using thiocyanate as the sulfur source and methanol as the methyl reagent. This protocol provides a green method for the thiomethylation of imidazopyridines without the need for any exogenous oxidants and metal catalysts under room temperature conditions. A wide range of functional groups were tolerated to produce regioselective C-3 thiomethylated products in high yields. Importantly, such an electrochemical-oxidation-induced thiomethylated reaction could be easily scaled up with excellent efficiency.

Iodine-Mediated Difunctionalization of Imidazopyridines with Sodium Sulfinates: Synthesis of Sulfones and Sulfides

Novel iodine-induced sulfonylation and sulfenylation of imidazopyridines have been described using sodium sulfinates as the sulfur source. This strategy enables highly selective difunctionalization of imidazo[1,2-a]pyridine to access sulfones and sulfides in good yields. A wide range of substrates and functional groups were well-tolerated under optimized conditions. Moreover, control experiments have been conducted, indicating a radical pathway involved in the reaction mechanisms.