13355-47-0

Upstream product

• 103-80-0 phenylacetyl chloride 
• 3340-78-1 2-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 591-50-4 iodobenzene 
• 91-21-4 1,2,3,4-tetrahydroisoquinoline 
• 41852-27-1 2-phenyl-3,4-dihydroisoquinolin-2-ium bromide 
• 100-58-3 phenylmagnesium bromide 
• 98-80-6 phenylboronic acid 
• 96718-77-3 N-Phenethyl-N-phenyl-benzamide 
• 1739-00-0 (N-phenyl)phenylethylamine 
• 621-06-7 2,N-diphenylacetamide 
• 103-82-2 phenylacetic acid 
• 1750-36-3 (E)-N-benzylidenebenzenamine 
• 59443-66-2 1,2-diphenyl-1,4-dihydro-2H-isoquinolin-3-one 
• 96719-09-4 1,2-Diphenyl-3,4-dihydro-isoquinolinium; iodide 

Relevant academic research and scientific papers

Efficient C(sp 3)-H Bond Arylation of Tetrahydroisoquinolines with Knochel-Type Arylzinc Reagents under Oxidative Conditions

A novel C(sp 3)-H bond arylation of tetrahydroisoquinoline (THIQ) derivatives with Knochel-type arylzinc reagents has been developed. In the presence of MgCl 2, arylzinc reagents readily reacted with THIQ derivatives under oxidative conditions, affording a wide range of potentially biologically active compounds in good yields. Moreover, the developed method can tolerate a variety of sensitive functional groups such as an ester group.

Copper-catalyzed asymmetric sp3 C-H arylation of tetrahydroisoquinoline mediated by a visible light photoredox catalyst

This report describes a highly enantioselective oxidative sp3 C-H arylation of N-aryltetrahydroisoquinolines (THIQs) through a dual catalysis platform. The combination of the photoredox catalyst, [Ir(ppy)2(dtbbpy)]PF6, and chiral copper catalysts provide a mild and highly effective sp3 C-H asymmetric arylation of THIQs.

One-pot functionalisation of N-substituted tetrahydroisoquinolines by photooxidation and tunable organometallic trapping of iminium intermediates

Nucleophilic trapping of iminium salts generated via oxidative functionalisation of tertiary amines is well established with stabilised carbon nucleophiles. The few reports of organometallic additions have limited scope of substrate and organometallic nucleophile. We report a novel, one-pot methodology that functionalises N - substituted tetrahydroisoquinolines by visible lightassisted photooxidation, followed by trapping of the resultant iminium ions with organometallic nucleophiles. This affords 1,2-disubstituted tetrahydroisoquinolines in moderate to excellent yields.

Direct sp3 C-H bond arylation, alkylation, and amidation of tetrahydroisoquinolines mediated by hypervalent iodine(iii) under mild conditions

We have developed a method for the sp3 C-H bond functionalization of tetrahydroisoquinolines (THIQs) mediated by [bis(trifluoroacetoxy)iodo]benzene (PIFA). The treatment of the THIQs with various nucleophiles in the presence of PIFA in a green solvent alternative gave the coupled products, with a C-C, C-N, or quaternary carbon center in high yields. This journal is

Simple and direct sp3 C-H bond arylation of tetrahydroisoquinolines and isochromans via 2,3-dichloro-5,6-dicyano-1,4- benzoquinone oxidation under mild conditions

The 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ)-mediated sp3 C-H bond arylation of tetrahydroisoquinolines and isochromans is described. The corresponding products were facilely synthesized via a simple nucleophilic addition reaction betwee

Copper-catalyzed oxidative sp3 C-H bond arylation with aryl boronic acids

(Chemical Equation Presented) An efficient method was developed for arylation of sp3 C-H bonds using copper bromide as catalyst in absence of directing group with arylboronic acids. The oxidative arylation provides easy access to biologically a

Superacid-promoted reactions of N-acyliminium ions: An effective route to substituted 3-oxo-1,2,3,4-tetrahydroisoquinolines and related products

Intramolecular cyclizations involving N-acyliminium ions are shown to give products in good yields from reactions with CF3SO3H (triflic acid). The resulting 3-oxo-1,2,3,4-tetrahydroisoquinolines have been converted in high yields to 1,2-diaryl-1,2,3,4-tetrahydroisoquinolines, which have been recently shown to be selective estrogen receptor modulators. In a reaction using a chiral N-acyliminium ion, cyclization is found to occur in moderately high diastereoselectivity. Several examples of intermolecular triflic acid-promoted reactions are also reported. Georg Thieme Verlag Stuttgart.

Antiimplantation Agents: Part II - 1,2-Diaryl-1,2,3,4-tetrahydroisoquinolines

1,2-Diaryl-3,4-dihydroisoquinolinium derivatives (5) have been synthesised from N-aryl-N-aroyl-β-phenethylamines (4) and found to exhibit no antiimplantation activity in the rat whereas many of the corresponding tetrahydroisoquinolines (6) are active.Structure-activity relationships have also been studied. 1-(p-Fluorophenyl)-6-methoxy-2-phenyl-1,2,3,4-tetrahydroisoquinoline (6u) and its nor derivative (6v) are very potent, while the ortho (6g) and the meta (6n) fluoro analogues as well as the des-fluoro derivative (6d) are quite active.Extensive biological tests have been carried out on 6g.The enantiomers (+)-6p*HCl and (-)-6q*HCl of 6n have similar activity profiles as that of 6n showing no separation of antiimplantation and estrogenic properties.Diastereomeric 2-(2-methyl-2-phenethyl)-1-phenyl-1,2,3,4-tetrahydroisoquinolines (13a and 13b) show similar properties, while the tetracyclic derivative 19 is inactive. 2-Phenoxyethyl-1-phenyl-1,2,3,4-tetrahydroisoquinoline (26) shows moderate activity, but 1-(β-phenethyl)-2-phenyl-1,2,3,4-tetrahydroisoquinoline 29 is inactive.