894792-11-1

Upstream product

• 98-85-1 1-Phenylethanol 
• 23612-57-9 (2-amino-3-pyridinyl)methanol 
• 120-72-9 indole 
• 15936-02-4 2-phenyl-1,8-naphthyridine 
• 98-86-2 acetophenone 
• 7521-41-7 2-Aminonicotinaldehyde 
• 1006-94-6 5-methoxylindole 

Downstream Products

• 894792-12-2 1-(2-(methylmercapto)-pyrimidin-4-yl)-7-phenyl-1,2,3,4-tetrahydro-1,8-naphthyridine 
• 894792-27-9 1-(2-fluoro-6-methylpyrimidin-4-yl)-7-phenyl-1,2,3,4-tetrahydro-1,8-naphthyridine 

Relevant academic research and scientific papers

Selective reductive cross-coupling of N-heteroarenes by an unsymmetrical PNP-ligated manganese catalyst

Reductive functionalization of N-heteroarenes remains to date a challenge due to the easy occurrence of direct reduction of such substances into non-coupling saturated cyclic amines. Herein, by developing an unprecedented manganese catalyst ligating with an unsymmetrical 2-aminotetrahydronaphthyridyl PNP-ligand, we have achieved a new reductive cross-coupling of indoles/pyrroles and N-heteroarenes. Mechanistic investigations show that the catalyst-enabled in situ capture of the partially reduced intermediates by interruption of the second transfer hydrogenation of N-heteroarenes constitutes the key to success for the present reaction. The developed chemistry proceeds with good substrate and functional group compatibility, high step and atom efficiency, excellent chemo and regioselectivity, and applicable for late-stage modification of pyridine-containing biomedical molecules, which has established a new platform allowing the linkage of aromatic systems into functional frameworks, and further development of unsymmetrical PNP organometallic complexes and related catalytic transformations.

Synthesis of Tetrahydroquinolines via Borrowing Hydrogen Methodology Using a Manganese PN3Pincer Catalyst

A straightforward and selective synthesis of 1,2,3,4-tetrahydroquinolines starting from 2-aminobenzyl alcohols and simple secondary alcohols is reported. This one-pot cascade reaction is based on the borrowing hydrogen methodology promoted by a manganese(I) PN3 pincer complex. The reaction selectively leads to 1,2,3,4-tetrahydroquinolines thanks to a targeted choice of base. This strategy provides an atom-efficient pathway with water as the only byproduct. In addition, no further reducing agents are required.

Transition metal-free α-methylation of 1,8-naphthyridine derivatives using DMSO as methylation reagent

A practical approach to the direct α-methylation of 1,8-naphthyridines under mild reaction conditions has been developed using simple and readily available DMSO as a convenient and environmentally friendly carbon source. This method is transition metal-free and highly chemoselective, shows good functional group tolerance, and uses DMSO as a methyl source, providing efficient and rapid access to an important compound class, 2-methyl-1,8-naphthyridines.

Selective synthesis of nitrogen bi-heteroarenes by a hydrogen transfer-mediated direct α,β-coupling reaction

By an external hydrogen transfer-mediated activation mode, we herein demonstrate a new palladium-catalyzed direct α,β-coupling of different types of N-heteroarenes. Such a selective coupling reaction proceeds with the advantages of operational simplicity,

Direct Access to Nitrogen Bi-heteroarenes via Iridium-Catalyzed Hydrogen-Evolution Cross-Coupling Reaction

Through cooperative actions of iridium catalyst and NaOTf additive we report a new direct access to nitrogen bi-heteroarenes via hydrogen-evolution cross-coupling of the β-site of indoles/pyrrole with the α-site of N-heteroarenes. The reaction proceeds in an atom- and redox-economic fashion together with the merits of an easily available catalyst system, broad substrate scope, excellent functional tolerance, and no need for external oxidants, offering a practical way to create π-conjugated systems.

Ruthenium-Catalyzed Straightforward Synthesis of 1,2,3,4-Tetrahydronaphthyridines via Selective Transfer Hydrogenation of Pyridyl Ring with Alcohols

Through a ruthenium-catalyzed selective hydrogen transfer coupling reaction, a novel straightforward synthesis of 1,2,3,4-tetrahydronaphthyridines from o-aminopyridyl methanols and alcohols has been developed. The synthetic protocol proceeds in an atom- a