41173-70-0

Upstream product

• 6283-04-1 N-phenethylpropionamide 
• 622-24-2 2-phenylethyl chloride 
• 7446-70-0 aluminium trichloride 
• 107-12-0 propiononitrile 
• 64-04-0 phenethylamine 
• 79-03-8 propionyl chloride 

Downstream Products

• 7661-60-1 1-ethyl-isoquinoline 
• 71612-01-6 11b-ethyl-2-methoxy-3,4-diphenyl-7,11b-dihydro-2H,6H-[1,3]thiazino[2,3-a]isoquinoline 
• 110229-17-9 4-Dicyanomethylen-1-methyl-2,3-diphenyl-4H-2,3,6,7-tetrahydropyridino<2.1-a>isochinolin 
• 109240-83-7 1-ethylidene-2-(2'-iodobenzoyl)-1,2,3,4-tetrahydroisoquinoline 
• 91417-05-9 3-imino-1-methyl-2-(4-nitrophenyl)-2,3,5,6-tetrahydrobenzoindolizin-2-ol 
• 91417-02-6 3-benzoylimino-1-methyl-2-(4-nitrophenyl)-2,3,5,6-tetrahydrobenzoindolizin-2-ol 
• 110229-20-4 4-Dicyanomethylen-1-methyl-2,3-diphenyl-4H-6,7-dihydropyridno<2.1-a>isochinolin 

Relevant academic research and scientific papers

Enantioselective Allylation of Cyclic and In Situ Formed N-Unsubstituted Imines with Tetraol-Protected Allylboronates

Tetraol-protected α-chiral allylboronates are utilized in diastereo- and enantioselective transformations of cyclic imines (up to 98 %, d.r. 97 : 3, e.r. 99 : 1). An application to in situ formed N-unsubstituted imines gives in a consecutive one-pot sequence selective access to all four stereoisomers of the homoallylamine within minutes (up to 88 %, d.r. 81 : 19, e.r. 99 : 1). These results underline the usability, tuneability and stability of tetraol-based allylboronates.

Identification of an Imine Reductase for Asymmetric Reduction of Bulky Dihydroisoquinolines

A new imine reductase from Stackebrandtia nassauensis (SnIR) was identified, which displayed over 25- to 1400-fold greater catalytic efficiency for 1-methyl-3,4-dihydroisoquinoline (1-Me DHIQ) compared to other imine reductases reported. Subsequently, an efficient SnIR-catalyzed process was developed by simply optimizing the amount of cosolvent, and up to 15 g L-1 1-Me DHIQ was converted completely without a feeding strategy. Furthermore, the reaction proceeded well for a panel of dihydroisoquinolines, affording the corresponding tetrahydroisoquinolines (mostly in S-configuration) in good yields (up to 81%) and with moderate to excellent enantioselectivities (up to 99% ee).

Additive-free pd-catalyzed α-allylation of imine-containing heterocycles

An additive-free Pd-catalyzed α-allylation of different imino-group-ontaining heterocycles is reported. The activation of α-CH pronucleophiles (pKa (DMSO) > 25) occurs without the addition of strong bases or Lewis acids using only the Pd/Xantphos catalyst system. The reaction scope has been studied for various 5- and 6-membered nitrogen-containing heterocycles (yields up to 96%). Mechanistic investigations suggest an initial allylation of the imine-N followed by a Pd-catalyzed formal aza-Claisen rearrangement.

A Titanium(III)-Catalyzed Reductive Umpolung Reaction for the Synthesis of 1,1-Disubstituted Tetrahydroisoquinolines

A catalytic reductive C1-acylation of 3,4-dihydroisoquinolines is presented that gives direct access to 1,1-disubstituted tetrahydroisoquinolines. The reaction is a titanium(III)-catalyzed reductive umpolung process in which nitriles act as effective acylation agents. The method is highly chemo- and regioselective and is demonstrated in 20 examples. It is well-suited for the large-scale synthesis of functionalized tetrahydroisoquinoline products, which is exemplified in the form of a six-step synthesis of (±)-3-demethoxyerythratidinone. (Figure Presented).

1,4-Dehydrochlorination of 1-(1-haloalkyl)-3,4-dihydroisoquinolines as a convenient route to functionalized isoquinolines

1-Chloroalkyl-, 1-(2,2-dichloroalkyl)-, and 1-(trichloromethyl)-3,4-dihydroisoquinolines are synthesized by chlorination of 1-alkyl-3,4-dihydroisoquinolines with N-chlorosuccinimide. These novel chlorinated 3,4-dihydroisoquinolines are suitable precursors for functionalized isoquinolines by aromatization involving sequential 1,4-dehydrochlorination, tautomerization, and nucleophilic substitution.

Synthesis of fused quinolizine derivatives by condensation of cyclic schiff bases with β-keto esters

A new procedure has been developed for the synthesis of fused nitrogen-containing heterocycles having a bridgehead nitrogen atom via condensation of cyclic Schiff bases with β-keto esters.

Amidine and isothiourea derivatives, compositions containing them and their use as inhibitors of nitric oxide synthase

There are provided novel compounds of formula (I) STR1 wherein X, R1, R2, R3, R4 and R5 are as defined in the specification and optical isomers and racemates thereof and pharmaceutically acceptable sa

REGIOPSPECIFIC OXIDATION OF SUBSTITUTED 1-BENZYL-3,4-DIHYDROISOQUINOLINES USING SINGLET OXYGEN

Singlet oxygen regiospecifically oxidizes 1-benzyl-3,4-dihydroisoquinoline to 1-benzoyl-3,4-dihydroisoquinoline.Mechanistic studies do not distinguish between a dioxetane or the alternative zwitterionic peroxide intermediate.