68263-23-0

Upstream product

• 81763-77-1 tert-Butyl-[1-(1-phenethyl-3,4-dihydro-1H-isoquinolin-2-yl)-meth-(E)-ylidene]-amine 
• 1428485-05-5 benzyl 1-(2-oxo-2-phenylethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate 
• 91-21-4 1,2,3,4-tetrahydroisoquinoline 
• 1337924-60-3 C₂₄H₂₀N₂O 
• 1337924-99-8 C₂₄H₂₄N₂O 
• 78317-83-6 2-(4-methoxyphenyl)-1,2,3,4-tetrahydroisoquinoline 
• 536-74-3 phenylacetylene 
• 81045-39-8 5,8-dibromoisoquinoline 
• 13735-81-4 1-styrenyloxytrimethylsilane 
• 90482-02-3 (S)-valinol-tert-butyl ether formamidine of 1,2,3,4 tetrahydro-isoquinoline 
• 103-63-9 1-phenyl-2-bromoethane 
• 79271-27-5 2-iodo-N-(2-phenylethyl)benzamide 
• 93816-58-1 1-phenethyl-3,4-dihydroisoquinoline 
• 501-52-0 3-Phenylpropionic acid 

Relevant academic research and scientific papers

Enhancement of the carbamate activation rate enabled syntheses of tetracyclic benzolactams: 8-oxoberbines and their 5- And 7-membered C-ring homologues

A route to the direct amidation of aromatic-ring-tetheredN-carbamoyl tetrahydroisoquinoline substrates was developed. This route enabled general access to 8-oxoberberines and their 5- and 7- membered C-ring homologues. It overcomes the undesired tandem side-reactions that result in the destruction of the isoquinoline backbone, which inevitably occurred under our previously reported superacidic carbamate activation method.

Diprotonative stabilization of ring-opened carbocationic intermediates: conversion of tetrahydroisoquinoline to triarylmethanes

Superacid-promoted conversion of tetrahydroisoquinolines to triarylmethanes via tandem reactions of C-N bond scission, Friedel-Crafts alkylation, C-O bond scission, and electrophilic aromatic amidation was developed. Dication formation was important for stabilizing the ring-opened carbocationic intermediate, which is a new role for diprotonation in reaction mechanisms. This journal is

Asymmetric Aerobic Oxidative Cross-Coupling of Tetrahydroisoquinolines with Alkynes

An efficient asymmetric aerobic oxidation of tetrahydroisoquinolines with terminal alkynes was realized under mild reaction conditions using O2 as the sole oxidant. A chiral N,N′-dioxide/zinc(II)/iron(II) bimetallic cooperative catalytic system

A metal-free cross-dehydrogenative coupling of N-carbamoyl tetrahydroisoquinoline by sodium persulfate

A metal-free cross-dehydrogenative coupling of N-carbamoyl tetrahydroisoquinoline with a variety of CH nucleophiles mediated by Na 2S2O8 is developed. The reaction proceeds smoothly to give the coupled product in up to 83%

Catalytic asymmetric alkynylation of C1-substituted C,N-cyclic azomethine imines by CuI/chiral bronsted acid co-catalyst

It all adds up: The title reaction was developed for the synthesis of chiral tetrahydroisoquinoline derivatives with a tetrasubstituted carbon center at the C1-position (see scheme, Bz=benzoyl, pybox=2,6-bis(2-oxazolinyl)pyridine) . The reaction was facilitated effectively by the co-catalyst system composed of copper(I)/Ph-pybox and an axially chiral dicarboxylic acid.

Asymmetric addition of nucleophiles to C-1 position of isoquinolines using (S)-alanine derivatives as chiral auxiliaries

5,8-Dibromoisoquinoline derivatives were allowed to react with a nucleophile (silyl enol ether or allyltributyltin) in the presence of an acyl chloride derived from (S)-alanine to afford the 1,2-addition products in good chemical yields and high stereoselectivity. The bromo groups were readily removed by a reduction process in which the double bond at C3-C4 was also reduced. Thus the reaction system provided a general method to synthesize asymmetric 1-substituted tetrahydroisoquinolines. In order to determine the absolute configuration of the reaction product, (-)-homolaudanosine was synthesized in an enantiopure form. The stereoselectivity was rationally understood from the conformation of intermediary N-acylated isoquinolinium salts.

DIPOLE STABILIZED α-AMINO CARBANIONS. II. ALKYLATION OF TETRAHYDROISOQUINOLINES IN THE 1-POSITION.

N-Formamidine derivatives of tetrahydroisoquinolines are metalated and alkylated to give 1-substituted derivatives.Regeneration of the parent amine is accomplished by several different reagents.