25308-72-9

Upstream product

• 1666-96-2 3-phenylquinoline 
• 22615-00-5 3-bromoquinoline N-oxide 
• 98-80-6 phenylboronic acid 
• 7534-40-9 2-phenylallyl acetate 
• 586-96-9 Nitrosobenzene 
• 19585-90-1 3-phenyl-quinoline-2,4-dicarboxylic acid 

Downstream Products

• 38035-81-3 3-phenyl-quinolin-2-ol 
• 25308-73-0 4-phenyl-benzo[d][1,3]oxazepine 
• 6319-32-0 4-chloro-3-phenylquinoline 
• 2859-30-5 2-chloro-3-phenyl-quinoline 

Relevant academic research and scientific papers

Cobalt-Catalyzed C8-Dienylation of Quinoline-N-Oxides

An efficient Cp*CoIII-catalyzed C8-dienylation of quinoline-N-oxides was achieved by employing allenes bearing leaving groups at the α-position as the dienylating agents. The reaction proceeds by CoIII-catalyzed C?H activation of qui

An efficient Pd(II)-(2-aminonicotinaldehyde) complex as complementary catalyst for the Suzuki-Miyaura coupling in water

An efficient new Pd(II)-(2-aminonicotinaldehyde)-catalyzed Suzuki-Miyaura coupling of the aryl halides (Br, Cl and I) and organoboronic acids at moderate temperature in water is described. Low catalyst loading, easy accessibility, being an air-stable catalyst, functional group compatibility, and water as the reaction medium are some of the key features of this synthetic method. This protocol is also applicable for gram scale.

Regioselective Cyanation of Six-Membered N-Heteroaromatic Compounds Under Metal-, Activator-, Base- and Solvent-Free Conditions

A regioselective cyanation of heteroaromatic N-oxides with trimethylsilyl cyanide has been developed to obtain 2-substituted N-heteroaromatic nitrile without the requirement of any external activator-, metal-, base-, and solvent. The present protocol is a straightforward, one-pot heteroaromatic C?H cyanation process, and proceeds smoothly in conventional heating but also under microwave irradiation with shorter reaction times. This approach now allows access to a broad class of quinoline N-oxides and other heteroarene N-oxides with high to good yields and can also be scaled up to obtain gram quantities. Further application of this process was observed and utilized in late-stage cyanation of the anti-malarial drug quinine as well as transformation of the 2-cyanoazines to a series of biologically important molecules. Based on the experimental observations, a plausible mechanism has also been proposed highlighting the dual role of trimethylsilyl cyanide as a nitrile source and as an activating agent. (Figure presented.).

Copper-Mediated [3+2] Annulation of 3-N-Hydroxyallylamines with Nitrosoarenes

Cu-mediated annulations of N-hydroxyallylamines with nitrosoarenes proceed through unprecedented formal [3+2] cycloadditions of N-hydroxyaminoallyl radicals with nitrosoarenes. Our mechanistic analysis opposes a 5-endo-trig cyclization involved in the final ring-closure step. To manifest the reaction utility, chemical elaborations of resulting isoxazolidinyl products into 2- or 3-substituted quinoline N-oxides and acyclic 1,3-diamino-2-ols are also described. Radical initiative! Cu-mediated annulations of N-hydroxyallylamines with nitrosoarenes proceed through unprecedented formal [3+2] cycloaddition reactions (see scheme). To manifest the reaction utility, chemical elaborations of resulting isoxazolidinyl products into 2- or 3-substituted quinoline N-oxides and acyclic 1,3-diamino-2-ols have been described.

Synthesis of 4-Aryl-2-aminopyridine derivatives and related compounds

A short, efficient, and high-yielding synthesis of 4-aryl-2-aminopyridine derivatives has been developed. The route employs two palladium-catalyzed processes, the Suzuki reaction and the Buchwald-Hartwig amination, as the key steps. The same approach has