59394-27-3

Upstream product

• 4965-33-7 2-methyl-7-chloroquinoline 
• 108-42-9 3-chloro-aniline 

Downstream Products

• 158966-92-8 montelukast 
• 151767-02-1 Montelukast sodium 
• 177748-00-4 7-chloro-2-ethenylquinoline 
• 1426678-85-4 N-((1H-indol-2-yl)methyl)-N-((6-bromoquinolin-2-yl)methyl)-4-methylbenzenesulfonamide 
• 1426679-10-8 6'-bromo-2-tosyl-1,2,3,3',4',9-hexahydro-1'H-spiro[pyrido[3,4-b]indole-4,2'-quinoline] 

Relevant academic research and scientific papers

Iodine-catalyzed oxidative annulation: Facile synthesis of pyrazolooxepinopyrazolones: Via methyl azaarene sp3C-H functionalization

An iodine-catalyzed methyl azaarene sp3 C-H functionalization has been developed for the synthesis of a seven-membered O-heterocyclic architecture containing three different heterocyclic aromatic hydrocarbons. This method can be applied to a wide range of substituted methyl azaarenes and diverse 2,4-dihydro-3H-pyrazol-3-ones, and brings about the efficient preparation of 2,9-dihydrooxepino[2,3-c:6,5-c′]dipyrazol-3(7H)-ones in high yields with the merits of low catalyst loading, good functional group tolerance and metal-free conditions.

Rh-Catalyzed Formal [3+2] Cyclization for the Synthesis of 5-Aryl-2-(quinolin-2-yl)oxazoles and Its Applications in Metal Ions Probes

A facile and efficient strategy for the synthesis of 5-aryl-2-(quinolin-2-yl)oxazoles via rhodium-catalyzed formal [3+2] cyclization of 4-aryl-1-tosyl-1H-1,2,3-triazoles with quinoline-2-carbaldehydes has been described. The protocol employs mild conditions and offers good yields of diverse 2,5-aryloxazole derivatives with a broad reaction scope. It is amenable to gram-scale synthesis and easily transformation. Moreover, this 5-aryl-2-(quinolin-2-yl)oxazole skeleton is indeed a new fluorophore and its applications in metal ions probes are also investigated and showed fluorescent responses to mercury ion.

Iodine-imine Synergistic Promoted Povarov-Type Multicomponent Reaction for the Synthesis of 2,2′-Biquinolines and Their Application to a Copper/Ligand Catalytic System

An efficient iodine-imine synergistic promoted Povarov-type multicomponent reaction was reported for the synthesis of a practical 2,2′-biquinoline scaffold. The tandem annulation has reconciled iodination, Kornblum oxidation, and Povarov aromatization, where the methyl group of the methyl azaarenes represents uniquely reactive input in the Povarov reaction. This method has broad substrate scope and mild conditions. Furthermore, these 2,2′-biquinoline derivatives had been directly used as bidentate ligands in metal-catalyzed reactions.

Facile synthesis of 1,3,4-oxadiazoles via iodine promoted oxidative annulation of methyl-azaheteroarenes and hydrazides

An oxidative sp3 C–H bond of methyl-azaheteroarenes protocol was reported for the synthesis of 1,3,4-oxadiazoles via [4 + 1] annulation with hydrazides. This protocol enables 1,3,4-oxadiazole and quinoline linked diheterocycles via selective oxidation of sp3 C–H bond of methyl-azaheteroarenes in the presence of I2-DMSO. The reaction has a broad substrate scope and good functional group tolerance for methyl-azaheteroarenes and hydrazides.

Iodine-catalyzed Csp3-H functionalization of methylhetarenes: One-pot synthesis and cytotoxic evaluation of heteroarenyl-benzimidazoles and benzothiazole

An efficient one-pot synthetic procedure has been developed for the preparation of heteroarenyl-benzimidazoles via oxidative Csp3-H functionalization with o-phenylenediamine using I2-DMSO in open air from easily available starting materials. Based on a logical plan a spectrum of multi fundamental reactions like iodination, Kornblum oxidation and amination were brought into one-pot. By using this simple method a library of heteroarenyl-benzimidazoles derivatives (3a–t and 5a–g) and heteroarenyl-benzothiazole (3u) have been synthesized in good to excellent yield and screened for their cytotoxicity against a group of four human cancer cell lines. Among them 3h, 3q and 5b showed significant cytotoxic activities with an IC50 of 1.69, 1.62 and 2.81 μM respectively against lung cancer (A549) cell line.[Figure presented]

Metal-free C(sp3)–H oxidation of 2-methylquinolines with PIDA under microwave irradiation

An efficient metal-free protocol has been developed for the sp3C–H bond oxidation of 2-methylquinolines in the presence of PIDA under microwave irradiation, providing 2-quinolinecarboxaldehydes with moderate to high yields and excellent selectivities. A wide range of 2-quinolinecarboxaldehydes with different functional groups have been synthesized. A tentative mechanism has been presented to explain this highly selective oxidation process.

Copper-Catalyzed Aerobic Oxidation of Azinylmethanes for Access to Trifluoromethylazinylols

A copper-catalyzed oxygenation of methylazaarenes was found to occur in the absence of both ligand and additive, and has been successfully employed for the synthesis of trifluoromethylazinylketols. This synthetic strategy incorporates aerobic oxidation and a trifluoromethylation in one-pot and provides a novel method for the trifluoromethylation of aliphatic C-H bond.

Acid-Activatable Michael-Type Fluorescent Probes for Thiols and for Labeling Lysosomes in Live Cells

A Michael addition is usually taken as a base-catalyzed reaction. Most fluorescent probes have been designed to detect thiols in slightly alkaline solutions (pH 7-9). The sensing reactions of almost all Michael-type fluorescent probes for thiols are faster in a high pH solution than in a low pH solution. In this work, we synthesized a series of 7-substituted 2-(quinolin-2-ylmethylene)malonic acids (QMAs, substituents: NEt2, OH, H, Cl, or NO2) and their ethyl esters (QMEs) as Michael-type fluorescent probes for thiols. The sensing reactions of QMAs and QMEs occur in distinct pH ranges, pH 7 for QMEs. On the basis of experimental and theoretic studies, we have clarified the distinct pH effects on the sensing reactivity between QMAs and QMEs and demonstrated that two QMAs (NEt2, OH) are highly sensitive and selective fluorescent probes for thiols in acidic solutions (pH 7) and promising dyes that can label lysosomes in live cells.

New and practical synthesis of montelukast sodium, an antiasthmatic drug

A new and practical synthesis of montelukast sodium, an antiasthmatic drug, is described. The key steps are the synthesis of nitrile derivative 4 by chiral reduction of keto ester 9 using (-)-DIP-Cl, synthesis of vinylquinoline framework 16 by Wittig reaction, and Heck coupling of nitrile 4 with vinylquinoline 16. The method is operationally simple and suitable for the industrial production of the drug substance. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental file.

OXAZOLYL PIPERIDINE MODULATORS OF FATTY ACID AMIDE HYDROLASE

Certain oxazolyl piperidine compounds are described, which are useful as FAAH inhibitors. Such compounds may be used in pharmaceutical compositions and methods for the treatment of disease states, disorders, and conditions mediated by fatty acid amide hydrolase (FAAH) activity. Thus, the compounds may be administered to treat, e.g., anxiety, pain, inflammation, sleep disorders, eating disorders, or movement disorders (such as multiple sclerosis).