75435-41-5

Upstream product

• 82342-56-1 N-benzoyl-1,2,3,4-tetrahydroisoquinoline 
• 132589-64-1 2-benzoyl-1,2,3,4-tetrahydro-isoquinoline-1-carboxylic acid 
• 62172-57-0 2-benzoyl-1,2,3,4-tetrahydroisoquinoline-1-carbonitrile 
• 91-21-4 1,2,3,4-tetrahydroisoquinoline 
• 100-52-7 benzaldehyde 
• 50458-78-1 ethyl isoquinoline-1-carboxylate 

Downstream Products

• 1196-38-9 3,4-dihydroisoquinolin-1(2H)-one 
• 65-85-0 benzoic acid 

Relevant academic research and scientific papers

Copper-Catalyzed Aldehyde Exchanged Amidation

The synthesis of bioactive amides has been the pursuit of chemists. Herein secondary amides incorporated with an aldehyde group were first generated using aldehydes and secondary amines. Various (hetero)aryl aldehydes and even aliphatic aldehydes (>40 examples) were converted into the desired products in moderate to excellent yields (up to 89%). A plausible mechanism involving a Cu(I/II/III) catalytic cycle combined with radical rearrangement was proposed and confirmed with four key intermediates detected by high-resolution mass spectrometry.

A g-C3N4-based heterogeneous photocatalyst for visible light mediated aerobic benzylic C-H oxygenations

A metal-free heterogeneous photocatalytic system has been developed for highly efficient benzylic C-H oxygenations using oxygen as an oxidant. This visible light mediated oxidation reaction utilizes graphitic carbon nitride (g-C3N4) as a recyclable, nontoxic and low cost photocatalyst. Mild reaction conditions allow for the generation of synthetically and biologically valued isochromannones, phthalides, isoquinolinones, isoindolinones and xanthones from readily accessible alkyl aromatic precursors in good yields. The heterogeneous nature of the g-C3N4 catalytic system enables easy recovery and recycling as well as the use in multiple runs without loss of activity. The synthetic utility of this "green" methodology was further demonstrated by applying in bioactive and drug valued target syntheses.

Radical oxidation of amides and related compounds with hypervalent tert- butylperoxyiodanes: Synthesis of imides and tert-butylperoxyamide acetals

tert-Butylperoxyiodane undergoes oxidation of the methylene groups α to the nitrogen atom of amides (or carbamates) yielding imides or tert- butylperoxyamide acetals, depending on the reaction conditions. A proposed mechanism involves generation of carbon-centered radicals α to the nitrogen atom.

Autoxidation of intermediary mesoionic 1,3-oxazolium-5-olates generated from cyclic N-acyl α-amino acids

Mesoionic 1,3-oxazolium-5-olates (munchnones) react fairly rapidly with oxygen to give the autoxidation products when the C-4 substituent is aromatic. The autoxidation occurred in the munchnones generated from N-acyl tetrahydroisoquinoline-1-carboxylic ac

Synthesis of 3,4-dihydroisoquinolines, 2-alkyl(acyl)-1(2H)-3,4-dihydroisoquinolinones, 2-alkyl-1(2H)-isoquinolinones and 1-alkyl-2(2H)-quinolinones by oxidation with potassium permanganate

Synthesis of 3,4-dihydroisoquinolines 2, 2-alkyl- 6 and 2-acyl-3,4-dihydro-1(2H)-isoquinolinones 9, 2-alkyl-1(2H)-isoquinolinones 14, N-alkyl-3,4-dihydro-2(2H)-quinolinones 16 and N-alkyl-2(2H)-quinolinones 19 by oxidation of 1,2,3,4-tetrahydroisoquinolines 1, N-alkyl (acyl)iminium salts of 3,4-dihydroisoquinolines 5,8 and isoquinoline 13 as well as of N-alkyl ammonium salts of tetrahydroquinoline 15 and quinoline 18 with potassium permanganate is described.

Unusual Formation of Tetrahydro-1-isoquinolones from Tetrahydroisoquinoline-1-carboxylic Acids with Carbodiimides and Mechanistic Aspects

The reaction of tetrahydroisoquinoline-1-carboxylic acids with carbodiimides leads to the formation of tetrahydro-1-isoquinolones in high yields, involving a reaction between mesoionic 1,3-oxazol-5-one intermediates and molecular oxygen.

OXYDATION OF TERTIARY POLYCYCLIC AMINES BY RuO4

The reactions of certain tertiary polycyclic amines such as N-benzyl-9-azabicyclo--nonane, N-benzyl-5,6-dihydro-11H-dibenzazepine, and N-benzyl-1,2,3,4-tetrahydroisoquinoline with ruthenium tetroxide, taking place in both heterogeneous and hom

Air oxidation of Reissert compounds

Reissert compounds undergo autoxidation in basic solution giving rise to isoquinaldo- or quinaldonitriles.Under the same reaction conditions, dihydroisoquinoline Reissert compounds undergo oxidative decyanation to dihydroisocarbostirils.The intermediacy of α-peroxycyanides is proposed in this transformation.