1198575-39-1

Upstream product

• 122-00-9 para-methylacetophenone 
• 501-65-5 diphenyl acetylene 
• 96475-75-1 (E)‐ 1‐(p‐tolyl)ethan‐1‐one O‐acetyl oxime 
• 42070-98-4 1-(p-tolyl)ethylamine 
• 1559065-82-5 N-chloro-1-(4-methylphenyl)ethanimine 
• 54582-23-9 1-p-tolylethanone oxime 
• 60672-33-5 4-methyl-N'-(1-(p-tolyl)ethylidene)benzenesulfonohydrazide 
• 60295-09-2 4'-methylacetophenone carbo-t-butoxyhydrazone 
• 71511-73-4 p-Methylacetophenon-acetylhydrazon 
• 85131-53-9 2-(1-methoxyiminoethyl)-5-methylbenzene 
• 21399-33-7 bis-(1-p-tolyl-ethylidene)-hydrazine 
• 64252-53-5 4-methylacetophenone hydrazone 
• 64252-52-4 1-(1-diazoethyl)-4-methylbenzene 
• 631-61-8 ammonium acetate 

Downstream Products

• 1383708-66-4 (E)-6-methyl-3,4-diphenyl-1-styrylisoquinoline 

Relevant academic research and scientific papers

Cobalt(III)-Catalyzed C-H/N-O Functionalizations: Isohypsic Access to Isoquinolines

C-H/N-O functionalizations by cobalt(III) catalysis allowed the expedient synthesis of a broad range of isoquinolines. Thus, internal and challenging terminal alkynes proved to be viable substrates for an isohypsic annulation, which was shown to proceed by a facile C-H cobaltation.

N-Tosylhydrazone as an oxidizing directing group for the redox-neutral access to isoquinolines via Cp?Co(III)-Catalyzed C–H/N–N activation

Herein, an efficient and economic access has been revealed for the synthesis of isoquinolines via C–H bond activation strategy by using comparatively inexpensive and versatile cobalt catalyst. A hardly investigated directing group, N-tosylhydrazone has been effectively applied as an internal oxidant for an annulation reaction with internal alkynes via C–H/N–N bond functionalization. This catalytic protocol works for the extensive variety of substrates in moderate to excellent yields under external oxidant-free conditions. Additionally, the proposed protocol has advantages such as broad substrate coverage with significant product yields, readily synthesized substrates as well as scalability up to the gram quantity which further improves the competency of the methodology.

Ruthenium-Catalyzed Annulation of N -Cbz Hydrazones via C-H/N-N Bond Activation for the Rapid Synthesis of Isoquinolines

In this work, N -Cbz hydrazone has been employed as a rarely explored directing group for the synthesis of isoquinolines by annulation with internal alkynes via C-H/N-N activation using Ru catalyst. Additive as well as external oxidant-free rapid protocol

Ruthenaelectro-Catalyzed Domino Three-Component Alkyne Annulation for Expedient Isoquinoline Assembly

The electrochemical three-component assembly of isoquinolines has been accomplished by ruthenaelectro-catalyzed C?H/N?H functionalization. The robustness of the electrocatalysis was reflected by an ample substrate scope, an efficient electrooxidation, and an operationally friendly procedure. The isolation of key intermediates and detailed mechanistic studies, including unprecedented cyclovoltammetric analysis of a seven-membered ruthenacycle, provided support for an unusual ruthenium(II/III/I) regime.

Rhodium-Catalyzed One-Pot Access to N-Polycyclic Aromatic Hydrocarbons from Aryl Ketones through Triple C-H Bond Activations

A Rh-catalyzed pot and step economic synthesis of aza-polycyclic aromatic hydrocarbons (N-PAHs) from readily available aryl ketones and alkynes has been disclosed. Additionally, a novel synthetic application of the well-known aminating reagent hydroxylamine-O-sulfonic acid (HOSA) has been explored as an in situ redox-neutral directing group for the formation of N-PAHs via isoquinoline. Multiple bond formation in a single operation through a cascade of triple C-H bond activations is the beauty of this protocol. The challenging annulations of two different alkynes in a regioselective fashion have been demonstrated effectively. Mechanistic studies reveal that 3,4-diphenyl-1-methylisoquinoline is an active intermediate for this one-pot transformation.

Rh(III)?catalyzed synthesis of isoquinolines from N-hydroxyoximes and alkynes in γ-valerolactone

A Rh (III)?catalyzed synthesis of isoquinoline derivatives from N-hydroxyoximes and alkynes via C–H activation/annulation process in biomass-derived γ-valerolactone (GVL) has been developed. A series of functional groups were well tolerated, affording the desired products in good to excellent yields.

Rh(III)-catalyzed synthesis of isoquinolines using the N-Cl bond of N-chloroimines as an internal oxidant

The Rh(III)-catalyzed coupling of N-chloroimines with alkynes for the efficient synthesis of isoquinolines is reported. This represents the first use of the N-Cl bond of N-chloroimines as an internal oxidant for construction of the isoquinoline skeleton. The synthesis features atom and step economy, a green solvent (EtOH), mild reaction conditions, and a broad substrate scope.

Hydroxylamine-O-Sulfonic Acid (HOSA) as a Redox-Neutral Directing Group: Rhodium Catalyzed, Additive Free, One-Pot Synthesis of Isoquinolines from Arylketones

A new application of hydroxylamine-O-sulfonic acid (HOSA) has been discovered whereby aromatic ketones react with HOSA and alkynes to form isoquinolines in the presence of a RhIII catalyst. This C–H/N–O annulation methodology gives excellent yields even without any silver additive, acid/base or metal oxidant. This is the first report wherein a directing group is simultaneously forming in situ, acting as acid additive, and also as an internal oxidant.

Eco-friendly synthesis method of 3, 4-disubstituted isoquinoline derivative promoted by room-temperature illumination

The invention discloses an eco-friendly synthesis method of a 3, 4-disubstituted isoquinoline derivative promoted by room-temperature illumination. The method comprises the following steps: by using water and polyethylene glycol 400 as a mixed solvent and a phenyl oxime compound and non-terminal alkyne as raw materials, synthesizing the 3, 4-disubstituted isoquinoline derivative at a room temperature under illumination. The method is a C-H coupling reaction catalyzed by a transition metal, and eco-friendly synthesis of the isoquinoline derivative can be simply and efficiently carried out. Compared with a traditional method, the method is safer, more economical and environmentally friendly, the functional group tolerance is good, the yield is high, extra photocatalysts and oxidizing agentsare not needed, the cost is reduced, the byproduct is H2O, the generation of a large amount of wastes is avoided, the atom utilization rate is improved, the substrate does not need to be pre-activatedand the reaction is carried out at room temperature, and the operation difficulty is reduced. According to the invention, a derivative molecular library of an isoquinoline ring with biological activity can be simply and rapidly supplemented, so that screening and discovery of new drug candidate molecules are facilitated.

Cp?-Free Cobalt-Catalyzed C-H Activation/Annulations by Traceless N, O-Bidentate Directing Group: Access to Isoquinolines

N,O-Bidentate directing-enabled, traceless heterocycle synthesis is described via Cp?-free cobalt-catalyzed C-H activation/annulation. The weakly coordinating nature of the carboxylic acid was employed for the preparation of isoquinolines. Meanwhile, the N-O bond of the α-imino-oxy acid can serve as an internal oxidant. Terminal as well as internal alkynes can be efficiently applied to the catalytic system. This operationally simple approach shows a broad substrate scope with the products obtained in good to excellent yields.