162334-78-3

Upstream product

• 132869-08-0 3-hydroxy-1-oxo-2-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 591-50-4 iodobenzene 
• 491-30-5 1-isoquinolone 
• 138528-62-8 E-1-methoxy-2-(2-carboxyphenyl)ethylene 
• 62-53-3 aniline 
• 872-36-6 vinylene carbonate 
• 93-98-1 N-phenyl benzoyl amide 
• 87992-94-7 1,2,3,4-tetrahydro-2-phenylisoquinolin-1-yl-1-phosphonic acid diethyl ester 
• 1382465-02-2 diphenyl(2‐phenyl‐1,2,3,4‐tetrahydroisoquinolin‐1‐yl)phosphine oxide 
• 1184912-58-0 dimethyl (2-phenyl-1,2,3,4-tetrahydroisoquinolin-1-yl)-phosphonate 
• 1184912-60-4 1,2,3,4-tetrahydro-2-phenylisoquinolin-1-yl-1-phosphonic acid diisopropy ester 
• 1322668-05-2 diphenyl (2-phenyl-1,2,3,4-tetrahydroisoquinolin-1-yl)phosphonate 
• 3340-78-1 2-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 38846-64-9 2-ethynylbenzaldehyde 

Downstream Products

• 6772-51-6 2-phenyl-3,4-dihydroisoquinolin-1(2H)-one 
• 77894-41-8 2,4-diphenylisoquinolin-1(2H)-one 

Relevant academic research and scientific papers

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

Mn(III) active site in hydrotalcite efficiently catalyzes the oxidation of alkylarenes with molecular oxygen

Developing efficient heterogeneous catalytic systems based on easily available materials and molecular oxygen for the selective oxidation of alkylarenes is highly desirable. In the present research, NiMn hydrotalcite (Ni2Mn-LDH) has been found as an efficient catalyst in the oxidation of alkylarenes using molecular oxygen as the sole oxidant without any additive. Impressive catalytic performance, excellent stability and recyclability, broad applicable scope and practical potential for the catalytic system have been observed. Mn3+ species was proposed to be the efficient active site, and Ni2+ played an important role in stabilizing the Mn3+ species in the hydrotalcite structure. The kinetic study showed that the aerobic oxidation of diphenylmethane is a first-order reaction over Ni2Mn-LDH with the activation energy (Ea) and pre-exponential factor (A0) being 85.7 kJ mol?1 and 1.8 × 109 min?1, respectively. The Gibbs free energy (ΔG≠) was determined to be -10.4 kJ mol-1 K-1 for the oxidation based on Eyring-Polanyi equation, indicating the reaction is exergonic. The mechanism study indicated that the reaction proceeded through both radical and carbocation intermediates. The two species were then trapped by molecular oxygen and H2O or hydroxyl species, respectively, to yield the corresponding products. The present research might provide information for constructing highly efficient and stable active site for the catalytic aerobic oxidation based on available and economic material.

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.).

Co(III)-Catalyzed Annulative Vinylene Transfer via C-H Activation: Three-Step Total Synthesis of 8-Oxopseudopalmatine and Oxopalmatine

The Co(III)-catalyzed redox-neutral annulation of benzamides and acrylamides with vinylene carbonate for the synthesis of isoquinolinones and pyridinones has been developed. This protocol employing inexpensive Co(III) as the catalyst tolerated diverse functional groups and substitution patterns, affording the target products with good to excellent yields. The synthetic utility of this transformation was demonstrated by a three-step synthesis of gusanlung D, 8-oxopseudopalmatine, and oxopalmatine.

Tandem Reaction Approaches to Isoquinolones from 2-Vinylbenzaldehydes and Anilines via Imine Formation-6π-Electrocyclization-Aerobic Oxidation Sequence

Two distinctive transition-metal-promoted aerobic oxidation protocols have been developed for the synthesis of isoquinolones from 2-vinylbenzaldehydes and aniline derivatives. Thus, the one-pot tandem reaction sequence of imine formation, thermal 6π-electrocyclization, followed by either Cu(OAc)2-mediated or Pd(OAc)2-catalyzed aerobic oxidation protocol allowed the ready access to isoquinolone derivatives. The control experiments revealed that the 1,2-dihydroisoquinoline intermediates from the 6π-electrocyclization of 1-azatrienes were aerobically oxidized to isoquinolones in the presence of either Cu(OAc)2 or Pd(OAc)2 catalyst.

Efficient and rapid synthesis of N-substituted isoquinolin-1-ones under mild conditions: Facile access to doryanine derivatives

We describe the simple and efficient synthesis of N-substituted isoquinolin-1-one derivatives. Initiating with the coupling of benzoic acids containing vinyl ethers with different amines, followed by rapid intramolecular cyclization under acidic conditions at room temperature, N-substituted isoquinolin-1-ones were furnished in high yields. The utility of this simple and mild cyclization method was demonstrated through the practical synthesis of natural product doryanine and its analogues.

C(sp2)-H Trifluoromethylation of enamides using TMSCF3: Access to trifluoromethylated isoindolinones, isoquinolinones, 2-pyridinones and other heterocycles

A method for the direct C(sp2)-H trifluoromethylation of enamides, including biologically relevant isoindolinones, isoquinolinones and 2-pyridinones using TMSCF3 under oxidative conditions is presented. The protocol is convenient, operationally simple and exhibits high tolerance across a multitude of relevant handles and functional groups.

Rhodium(III)-Catalyzed Annulation of Pyridinones with Alkynes via Double C-H Activation: A Route to Functionalized Quinolizinones

A Rh(III)-catalyzed oxidative annulation of pyridin-2(1H)-ones with alkynes via double C-H activation to produce highly functionalized 4H-quinolizin-4-ones is disclosed. This reaction features easily available starting materials, simple manipulation, a relatively wide substrate scope, and good functional group tolerance. The application of this protocol is demonstrated by the synthesis of a known fluorescent quinolizino[3,4,5,6-ija]quinolinium salt.

Aerobic oxidation of amines catalyzed by polymer-incarcerated au nanoclusters: Effect of cluster size and cooperative functional groups in the polymer

Aerobic oxidation reaction of amines to imines catalyzed by polymer-incarcerated Au nanoclusters (PI-Au) was developed. The effect of cluster size for this oxidation reaction was carefully examined using the same polymer support. We have succeeded in preparation of various PI-Au catalysts containing different size clusters by modification of standard preparation methods. The size of clusters and their distribution were analyzed by electron microscopy. Interestingly, catalysts containing relatively larger clusters (>5 nm) showed higher activity in aerobic oxidation of amines than catalysts containing smaller clusters (13 nm) that showed much better activity for aerobic oxidation of alcohols. In addition, novel Au nanocluster catalysts immobilized on newly prepared polymer with tertiary amine groups were developed and they showed excellent activity for aerobic oxidation of amines to imines. The relation between cluster size and catalytic activity and role of tertiary amine in polymer were discussed. These catalysts could be applied to aerobic oxidative deprotection of p-methoxybenzyl groups.

A facile copper-catalyzed Ullmann condensation: N-arylation of heterocyclic compounds containing an -NHCO- moiety

N-Aryl heterocyclic compounds were synthesized from aryl halides and heterocyclic compounds containing an -NHCO- moiety by using a catalytic amount (1-10 mol%) of a commercially available copper catalyst in satisfactory yields. This catalytic reaction was applicable to the synthesis of N-aryl-2-pyridone, -2-pyrrolidone, -1(2H)-isoquinolone, -1(2H)- phthalazinone, -4(3H)-quinazolinone and -1,2,3-benzotriazin-4(3H)-one derivatives.