6772-66-3

Upstream product

• 78317-82-5 2-(p-tolyl)-1,2,3,4-tetrahydroisoquinoline 
• 75-52-5 nitromethane 
• 1132765-75-3 1-(nitromethyl)-2-(p-tolyl)-1,2,3,4-tetrahydroisoquinoline 
• 91-21-4 1,2,3,4-tetrahydroisoquinoline 
• 624-31-7 4-tolyl iodide 
• 28269-50-3 2-vinylbenzoic acid chloride 
• 106-49-0 p-toluidine 
• 106-38-7 para-bromotoluene 
• 87992-99-2 diethyl 2-(4-methylphenyl)-1,2,3,4-tetrahydroisoquinoline-1-yl-phosphonate 
• 119-65-3 isoquinoline 
• 23438-23-5 4-hydroxy-4-methyl-cyclohexa-2,5-dienone 
• 135-19-3 β-naphthol 

Relevant academic research and scientific papers

Redox-neutral functionalization of α-Csp3-H bonds of secondary cyclic amines: a highly atom-economical strategy forN-arylation/formal cross-dehydrogenative couplings

An efficient redox-neutral method has been developed for α-Csp3-H functionalization of secondary cyclic aminesviaconcurrentN-arylation/formal cross dehydrogenation coupling (CDC) with sp2-C-H and sp3-C-H bonds of arenes an

Covalent Organic Frameworks toward Diverse Photocatalytic Aerobic Oxidations

Photoactive two-dimensional covalent organic frameworks (2D-COFs) have become promising heterogenous photocatalysts in visible-light-driven organic transformations. Herein, a visible-light-driven selective aerobic oxidation of various small organic molecules by using 2D-COFs as the photocatalyst was developed. In this protocol, due to the remarkable photocatalytic capability of hydrazone-based 2D-COF-1 on molecular oxygen activation, a wide range of amides, quinolones, heterocyclic compounds, and sulfoxides were obtained with high efficiency and excellent functional group tolerance under very mild reaction conditions. Furthermore, benefiting from the inherent advantage of heterogenous photocatalysis, prominent sustainability and easy photocatalyst recyclability, a drug molecule (modafinil) and an oxidized mustard gas simulant (2-chloroethyl ethyl sulfoxide) were selectively and easily obtained in scale-up reactions. Mechanistic investigations were conducted using radical quenching experiments and in situ ESR spectroscopy, all corroborating the proposed role of 2D-COF-1 in photocatalytic cycle.

Oxidation of the inert sp3C-H bonds of tetrahydroisoquinolines through C-H activation relay (CHAR): construction of functionalized isoquinolin-1-ones

A TBN/O2-initiated oxidation of the relatively inert 3,4-C-H bonds of THIQs was accomplished, in which the existence of an α-phosphoric ester group is crucial to enable dioxygen trapping and intramolecular HAT (C-H activation relay,CHAR), reali

Porphyrin-Catalyzed Oxidation of N-Substituted Tetrahydroisoquinolines to Dihydroisoquinolones

A visible-light-induced direct α-oxygenation of N-substituted 1,2,3,4-Tetrahydroisoquinoline derivatives has been successfully developed. Tetraphenylporphyrinatozinc(II) has been identified as an effective and inexpensive photocatalyst for this transformation with a wide range of substrates. This protocol provides a convenient route to the desired products in moderate to good yields at room temperature under air.

Visible-Light-Induced Controlled Oxidation of N-Substituted 1,2,3,4-Tetrahydroisoquinolines for the Synthesis of 3,4-Dihydroisoquinolin-1(2H)-ones and Isoquinolin-1(2H)-ones

A visible light-rose bengal-TBHP mediated, controlled oxidation of N-substituted 1,2,3,4-tetrahydroisoquinolines is developed for the synthesis of 3,4-dihydroisoquinolin-1(2H)-ones and isoquinolin-1(2H)-ones. The present method feature's a broad substrate scope, good functional group tolerances, and the products were prepared in good to excellent yields. The developed methodology further demonstrated in the synthesis of isoindolo[2,1-b] isoquinolin-5(7H)-one (topoisomerase-I inhibitor). (Figure presented.).

Phenazine Radical Cations as Efficient Homogeneous and Heterogeneous Catalysts for the Cross-Dehydrogenative Aza-Henry Reaction

The redox activity of molecular phenazine catalysts has been previously exploited for aerobic oxidative amine homo- and cross-coupling reactions. In this contribution, we have extended the reaction scope of this novel type of organocatalyst and used them in the cross-dehydrogenative aza-Henry coupling of isoquinolines with nitromethane under aerobic conditions. Additionally, we have designed and prepared a novel porous organic polymer by cross-linking of tetrakis(4-bromophenyl)silane and dihydrophenazine through Pd-catalyzed Buchwald-Hartwig cross-coupling. This new type of heterogeneous catalyst, apart from being robust and easily reusable, also showed outstanding catalytic activities and improved selectivity compared to its molecular counterpart. A plausible reaction mechanism was proposed based on spectroscopic and kinetic measurements.

PIFA-Promoted, Solvent-Controlled Selective Functionalization of C(sp2)-H or C(sp3)-H: Nitration via C-N Bond Cleavage of CH3NO2, Cyanation, or Oxygenation in Water

A novel nitration (via C(sp3)-N breaking/C(sp2)-N formation with CH3NO2) mediated by [bis(trifluoroacetoxy)iodo]benzene (PIFA) is described. The NO2 transfer from CH3NO2 to the aromatic group of the substrate is possible with careful selection of the solvent, NaX, and oxidant. In addition, the solvent-controlled C(sp2)-H functionalization can shift to an α-C(sp3)-H functionalization (cyanation or oxygenation) of the α-C(sp3)-H of cyclic amines.

Aerobic α-Oxidation of N-Substituted Tetrahydroisoquinolines to Dihydroisoquinolones via Organo-photocatalysis

An efficient visible-light-induced α-oxidation of N-substituted tetrahydroisoquinolines to dihydroisoquinolones has been developed using eosin Y as an organo-photocatalyst and oxygen as a green oxidant. The reactions were carried out under mild reaction conditions; the desired dihydroisoquinolones were obtained in up to 96% yield at room temperature under oxygen atmosphere. This transformation provides a convenient route to dihydroisoquinolones with a wide range of substrates. (Figure presented.).

α-Angelica Lactone in a New Role: Facile Access to N-Aryl Tetrahydroisoquinolinones and Isoindolinones via Organocatalytic α-CH2 Oxygenation

A method for the direct oxidation of various N-aryl tetrahydroisoquinolines and isoindolines to the corresponding lactams using α-angelica lactone as a catalyst was developed. The utility of the method was further demonstrated by synthesis of indoprofen and indobufen.

Diethyl Phosphite Promoted Electrochemical Oxidation of Tetrahydroisoquinolines to 3,4-Dihydroisoquinolin-1(2 H)-ones

A diethyl phosphite mediated electrochemical oxidation strategy for the synthesis of 3,4-dihydroisoquinolin-1(2 H)-ones from tetrahydroisoquinolines under mild conditions has been developed. This protocol provides an environmentally friendly and simple way for the construction of C=O bonds in an undivided cell unit.