1126793-06-3

Upstream product

• 100-52-7 benzaldehyde 
• 129986-67-0 N-methoxy-N-methyl-2-(triphenylphosphoranylidene)acetamide 
• 15111-14-5 2-iodo-N-(phenylmethylene)-benzenamine 
• 1126793-02-9 2-iodo-N-methyl-N-(1-phenylbut-3-en-1-yl)aniline 
• 615-43-0 2-iodophenylamine 
• 154225-11-3 N-(4-phenyl-1-buten-4-yl)-2-iodobenzenamine 

Downstream Products

• 1126793-28-9 N-methoxy-N-methyl-2-[(2R,4R)-1-methyl-2-phenyl-1,2,3,4-tetrahydroquinolin-4-yl]acetamide 
• 1126793-24-5 N-methoxy-N-methyl-2-[(2S,4R)-1-methyl-2-phenyl-1,2,3,4-tetrahydroquinolin-4-yl]acetamide 

Relevant academic research and scientific papers

Intramolecular Mizoroki-Heck reaction in the regioselective synthesis of 4-alkylidene-tetrahydroquinolines

The Mizoroki-Heck reaction of N-alkenyl-substituted 2-haloanilines is an effective protocol for the synthesis of substituted 4-alkylidene- tetrahydroquinoline derivatives, avoiding isomerization and oxidation. When non-substituted alkenes are used, the regioselectivity of the reaction can be directed towards the formation of an exocyclic or endocyclic double bond by choosing an adequate catalytic system. When the double bond is substituted by an amide moiety, the exocyclic double bond of E geometry is obtained selectively. Thus, this protocol efficiently synthesizes a series of 2-substituted tetrahydroquinolines with an exo α,β-unsaturated amide moiety at the C-4 position. Optimal conditions for Mizoroki-Heck reactions of N-alkenyl-substituted 2-haloanilines have been developed to access 4-alkylidene-tetrahydroquinoline derivatives regioselectively, avoiding isomerization and oxidation. Copyright

Intramolecular carbolithiation reactions for the synthesis of 2,4-disubstituted tetrahydro-quinolines: Evaluation of TMEDA and (-)-sparteine as ligands in the stereoselectivity

The preparation of 4-substituted 2-phenyltetrahydroquinolines from N-alkenylsubstituted 2-iodoanilines via intramolecular carbolithiation reactions has been investigated. The stereochemical outcome of the carbolithiation reactions depends on the nature of organolithium employed to perform the lithium-halogen exchange, the solvent, or the use of additives, for example, TMEDA or chiral bidentated ligands such as (-)-sparteine. Thus, the 2,4-disubstituted tetrahydroquinolines are obtained with moderate diastereoselectivities (up to 77:23) and with ee up to 94% when Weinreb amide derivatives are used (R) CONMe(OMe)).