49669-15-0

Usage

Type of compound

Organic compound

Structure

Heterocyclic compound with a pyridine ring fused to a dioxolane ring and a methyl group attached to the dioxolane ring

Usage

Building block in the synthesis of pharmaceuticals and agrochemicals

Potential

Ligand in coordination chemistry for the stabilization of metal complexes, applications in organic electronics and materials science

InChI:InChI=1/C9H11NO2/c1-9(11-6-7-12-9)8-4-2-3-5-10-8/h2-5H,6-7H2,1H3

Upstream product

• 49669-14-9 2‐bromo‐6‐(2‐methyl‐1,3‐dioxolan‐2‐yl)pyridine 
• 1122-62-9 2-acetylpyridine 
• 107-21-1 ethylene glycol 
• 49669-13-8 1-(6-bromopyridin-2-yl)-ethanone 
• 109-04-6 2-bromo-pyridine 
• 764-48-7 ethyleneglycol vinyl ether 

Downstream Products

• 243669-95-6 1-benzyl-2-acetylpiperidine 
• 502763-03-3 1'-[2-(N-benzylpiperidyl)]ethenyl 2,4-hexadienoate 
• 502763-02-2 1-benzyl-2-(1',1'-ethylenedioxy)ethylpyridine 
• 106318-66-5 1-(2-piperidyl)ethanone hydrochloride 
• 59275-44-4 1-(2,5-dimethyl-benzyl)-2-(2-methyl-[1,3]dioxolan-2-yl)-pyridinium; bromide 
• 3340-19-0 1-(2-Sulfo-benzyl)-2-<2-methyl-1,3-dioxolanyl-(2)>-pyridiniumhydroxid-betain 

Relevant academic research and scientific papers

Discovery of a series of phosphonic acid-containing thiazoles and orally bioavailable diamide prodrugs that lower glucose in diabetic animals through inhibition of fructose-1,6-bisphosphatase

Oral delivery of previously disclosed purine and benzimidazole fructose-1,6-bisphosphatase (FBPase) inhibitors via prodrugs failed, which was likely due to their high molecular weight (>600). Therefore, a smaller scaffold was desired, and a series of phosphonic acid-containing thiazoles, which exhibited high potency against human liver FBPase (IC50 of 10-30 nM) and high selectivity relative to other 5′-adenosinemonophosphate (AMP)-binding enzymes, were discovered using a structure-guided drug design approach. The initial lead compound (30j) produced profound glucose lowering in rodent models of type 2 diabetes mellitus (T2DM) after parenteral administration. Various phosphonate prodrugs were explored without success, until a novel phosphonic diamide prodrug approach was implemented, which delivered compound 30j with good oral bioavailability (OBAV) (22-47%). Extensive lead optimization of both the thiazole FBPase inhibitors and their prodrugs culminated in the discovery of compound 35n (MB06322) as the first oral FBPase inhibitor advancing to human clinical trials as a potential treatment for T2DM.

Palladium-catalyzed regiocontrolled internal heteroarylation of electron-rich olefins with heteroaryl halides

A highly efficient palladium-catalyzed Heck coupling reaction of heteroaryl halides with electron-rich vinyl ether and hydroxyalkyl vinyl ethers is described. It was found that the choice of solvent, ligand, and reaction temperature had a fundamental influence on the regioselectivity and reactivity of the reaction, and the combination of Pd(OAc)2 and DPPF in ethylene glycol led to the most effective catalytic system. Under these conditions, a variety of heteroaryl halides reacted very quickly with electron-rich olefins to afford exclusively the branched products in good to excellent yields without employing triflates, halide scavengers, or ionic liquids.

A formal total synthesis of securinine via an intramolecular [4+2] cycloaddition reaction

An intramolecular Diels-Alder reaction of the enol ester derived from 2-acetylpyridine and sorbic anhydride gave the cycloaddition product, stereoselectively, which was further converted into the key intermediate for the synthesis of securinine.

Novel Transformations Leading to 3-Benzylindolizidin-2-ones

Several derivatives of keto amide 10 have been prepared and their cyclization reactions investigated.Oxime 11 and 2,4-dinitrophenylhydrazone 12 cyclize to give isoxazolidine 16 and pyrazolidine 17, respectively, under acidic conditions (Scheme II).Oxime 1