35482-56-5

Usage

InChI:InChI=1/C12H12N2O3/c1-3-17-12(16)9-6-13-11-8(10(9)15)5-4-7(2)14-11/h4-6H,3H2,1-2H3,(H,13,14,15)

Upstream product

• 1824-81-3 2-Amino-6-methylpyridine 
• 87-13-8 diethyl 2-ethoxymethylenemalonate 
• 13250-95-8 diethyl 2-{[(6-methyl-2-pyridyl)amino]methylene}propane-1,3-dioate 
• 16867-53-1 3-Ethoxycarbonyl-6-methyl-4-oxo-4H-pyrido<1,2-a>pyrimidine 
• 80287-53-2 5-Amino-2-methylpyridine 

Downstream Products

• 13317-11-8 1,4-Dihydro-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylic acid 
• 33331-59-8 ethyl 1-ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate 
• 868695-99-2 7-methyl-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid 4-nitro-benzylamide 
• 1569-18-2 7-methyl-1,8-naphthyridin-4-ol 
• 1076222-50-8 (7-methyl-[1,8]naphthyridin-4-yl)-(5-methyl-2-phenylsulfanylphenyl)-amine hydrochloride 

Relevant academic research and scientific papers

On the Regioselectivity of the Gould–Jacobs Reaction: Gas-Phase Versus Solution-Phase Thermolysis

A detailed investigation of the regioselectivity in the thermal cyclization of (pyridyl)aminomethylenemalonates both in the gas- and solution phase is presented. Flash vacuum pyrolysis (FVP) as a gas-phase thermolysis technique is used to study the Gould–Jacobs reaction at temperatures between 450–650 °C, while different solution-phase heating techniques (reflux, microwave, and continuous flow) were employed at 260–350 °C. Depending on the position of the substituent in the pyridine moiety and the applied thermolysis technique, the regioselectivity of the cyclization can be controlled either in favor of the kinetic (pyridopyrimidinone) or the thermodynamic (naphthyridinone) product. Under FVP conditions, 6-substituted pyridopyrimidinones were obtained in high regioselectivity, which was not demonstrated before under standard Gould–Jacobs reaction conditions. DFT calculations have been additionally performed to provide further insights into the mechanistic pathways of this specific Gould–Jacobs reaction.

Design, synthesis and structure-activity-relationship of 1,5-tetrahydronaphthyridines as CETP inhibitors

This Letter describes the discovery and SAR optimization of 1,5-tetrahydronaphthyridines, a new class of potent CETP inhibitors. The effort led to the identification of 21b and 21d with in vitro human plasma CETP inhibitory activity in the nanomolar range (IC50 = 23 and 22 nM, respectively). Both 21b and 21d exhibited robust HDL-c increase in hCETP/hApoA1 dual heterozygous mice model.

Limitations of the Jacobs-Gould reaction using microwave irradiation

Upon investigating the green synthesis of some antimicrobial quinolone compounds, some atypical ring-closing patterns were observed during the synthesis of various intermediates using the Jacobs-Gould reaction.

ANTI-VIRAL COMPOUNDS

Compounds effective in inhibiting replication of Hepatitis C virus ( HCV ) or other viruses are disclosed. This invention is also directed to compositions comprising such compounds, coformulation or co-administration of such compounds with other anti-viral or therapeutic agents, processes and intermediates for the syntheses of such compounds, and methods of using such compounds for the treatment of HCV or other viral infections.

SUBSTITUTED QUINOLONES AND METHODS OF USE

Substituted quinolone compounds and compositions are provided along with methods for the use of those compounds in the treatment of diseases and disorders such as cancer.

2-Arylindoles as gonadotropin releasing hormone (GnRH) antagonists: Optimization of the tryptamine side chain

A series of 2-arylindoles containing novel heteroaromatic substituents on the tryptamine tether, based on compound 1, was prepared and evaluated for their ability to act as gonadotropin releasing hormone (GnRH) antagonists. Successful modifications of 1 included chain length variation (reduction) and replacement of the pyridine with heteroaromatic groups. These alterations culminated in the discovery of compound 27kk which had excellent in vitro potency and oral efficacy in rodents.

Synthesis and evaluation of quinoline carboxyguanidines as antidiabetic agents

The synthesis and in vivo activities of a series of substituted quinoline carboxyguanidines as a possible novel class of antidiabetic agents is described. (C) 2000 Elsevier Science Ltd. All rights reserved.

Invited review. A combinatorial approach to the development of environmentally benign organic chemical preparations

Enabling technologies and methodologies were established and combined to afford various environmentally benign processes for laboratory-scale organic synthesis and for the production of fine chemicals, intermediates and pharmaceuticals. The technologies comprised continuous and batch microwave reactors and catalytic membranes. The methodologies included solvent-free conditions, catalysed or uncatalysed processes, the use of aqueous media at high temperature and non-extractive techniques for product isolation. Applications included Hofmann eliminations, Willgerodt and Jacobs-Could reactions, indole transformations, aldol condensation, Rupe and Meyer-Schuster rearrangements and C-C coupling reactions (including a tandem Heck coupling-dehydrogenation). New processes for catalytic etherification, uncatalysed hydrogen transfer and a one-step arylamidation were also developed. Typical products were N-(4-hydroxyphenyl)acetamide, carvacrol, α-phenylacetamide, cinnamaldehyde, cinnamyl alcohol, acetophenone, indole, 3-hydroxy-1,2-dimethyl-4-pyridone, di(2-phenylethyl) ether, di(cyclopropylmethyl) ether, 3-methylcyclopent-2-enone and a synthetic precursor of nalidixic acid.