1198575-55-1

Upstream product

• 3349-64-2 1-tetralone oxime 
• 501-65-5 diphenyl acetylene 
• 529-34-0 3,4-dihydronaphthalene-1(2H)-one 
• 1559065-85-8 N-chloro-3,4-dihydronaphthyl-1(2H)-imine 
• 2217-40-5 1,2,3,4-tetrahydronaphthalen-1-amine 
• 17336-59-3 1-tetralone tosylhydrazone 
• 182422-07-7 1-tetralone carbo-t-butoxyhydrazone 
• 66575-46-0 1,2-bis[3,4-dihydronaphthalen-1(2H)-ylidene]hydrazine 
• 5736-43-6 (3,4-dihydronaphthalen-1(2H)-ylidene)hydrazine 
• 107820-92-8 1,2,3,4-tetrahydro-1-diazonaphthalene 
• 631-61-8 ammonium acetate 
• 1613470-74-8 (1E,2E)-1,2-bis(3,4-dihydronaphthalen-1(2H)-ylidene)hydrazine 
• 1536277-97-0 C₁₂H₁₄N₂ 
• 28353-74-4 (E)-3,4-dihydronaphthalen-1(2H)-one O-acetyl oxime 

Relevant academic research and scientific papers

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 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.

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.

Rapid and Atom Economic Synthesis of Isoquinolines and Isoquinolinones by C–H/N–N Activation Using a Homogeneous Recyclable Ruthenium Catalyst in PEG Media

Herein, we report an atom-efficient, rapid, green, and sustainable approach to synthesize isoquinolines and isoquinolinones using a homogeneous recyclable ruthenium catalyst in PEG Media assisted by microwave energy. Dibenzoylhydrazine was used for C–H/N–N activation reactions for the first time in combination with ketazine as oxidizing directing groups for annulation reactions with internal alkynes. The developed protocol is environmentally benign due to significantly shortened times with an easy extraction method, higher atom economy, external oxidant and silver or antimony salt free conditions, applicability to a gram scale synthesis, use of biodegradable solvent and wide substrate scope with higher product yields. Moreover, it is worth noting that the established methodology allowed reuse of the catalytic system for up to five successive runs with minimal loss in activity.

Easy access to synthesize isoquinolines from aryl ketoximes and internal alkynes via Iridium (III)-catalyzed C[sbnd]H/N[sbnd]O bond activation

A highly efficient approach to synthesize isoquinoline derivatives through Iridium(III)-catalyzed cyclization of aryl ketoximes and internal alkynes without oxidant is reported. A broad range isoquinolines are obtained in good to excellent yields and various functional groups are well tolerated.

N-Tosylhydrazone directed annulation via C-H/N-N bond activation in Ru(ii)/PEG-400 as homogeneous recyclable catalytic system: a green synthesis of isoquinolines

A green and sustainable methodology for the synthesis of isoquinolines using Ru(ii)/PEG-400 as a homogeneous recyclable catalytic system has been demonstrated. N-Tosylhydrazone, a rarely explored directing group, has been successfully employed for an annu

Rhodium-Catalyzed Oxidative Cycloaddition of N-tert-Butoxycarbonylhydrazones with Alkynes for the Synthesis of Functionalized Pyrroles via C(sp3)–H Bond Functionalization

A rhodium(III)-catalyzed cycloaddition of N-tert-butoxycarbonylhydrazones with internal alkynes was developed. The reaction features a regioselective α-imino alkyl C(sp3)?H bond functionalization resulting in selective formation of highly functionalized NH-free pyrroles. Our studies showed that utilizing the N-tert-butoxycarbonyl (N-Boc) as the oxidizing directing group is critical for achieving the observed pyrrole formation versus the isoquinoline formation. To account for the pyrrole formation, we hypothesized that a prior tautomerization of the N-Boc-hydrazones to enamines should occur, followed by regioselective C(sp2)–H cleavage to form a putative five-membered rhodacycle. Subsequent coupling of the rhodacycle with the alkynes would afford the pyrrole products. (Figure presented.).

A kind of high-efficient synthetic indole and isoquinoline derivatives (by machine translation)

The invention discloses a substituted indole and isoquinoline preparation method, which belongs to the technical field of organic chemical synthesis. This method adopts the oxygen as the oxidizing agent, various substituents substituted alkyne starting material of the aromatic amine or [...] , by transition metal-catalyzed, get containing indole or isoquinoline compound of the structure. The reaction raw material, oxidizing agent and cheap and easily obtained catalyst, synthesis technique is simple, which greatly reduces the cost of synthesizing; mild reaction conditions, high yield, easy industrialization; reaction raw materials and catalyst cleaning non-toxic, small pollution to the environment. Such compounds and their derivatives as an important fine chemicals, in the medical, agricultural chemicals, perfume and widely used photoelectric and other industries. (by machine translation)

CpCo(III)-Catalyzed C-H/N-N Functionalization of Arylhydrazones for the Synthesis of Isoquinolines

Cationic Co(III)-catalyzed C-H/N-N bond functionalization of arylhydrazones with internal alkynes has been developed for the synthesis of isoquinoline derivatives. The arylhydrazones are easy to prepare and require inexpensive and commercially available hydrazine hydrate. The reaction works well with a variety of internal alkynes and arylhydrazones and offers broad scope, good functional group tolerance, and high yields under redox-neutral conditions in the presence of air.

Easy Access to 1-Amino and 1-Carbon Substituted Isoquinolines via Cobalt-Catalyzed C - H/N - O Bond Activation

A green atom-economical method for the synthesis of highly functionalized 1-amino and 1-carbon substituted isoquinolines from the reaction of N′-hydroxybenzimidamides and aryl ketoximes, respectively, with alkynes via pentamethylcyclopentadienylcobalt(III)-catalyzed C - H/N - O bond activation is described. The external oxidant-free annulation reaction uses the =NOH moiety in N′-hydroxybenzimidamides or N-aromatic ketone oximes as the directing group and internal oxidant. This first row transition metal-catalyzed annulation serves as an efficient alternative for the synthesis of isoquinolines, as water is the only by-product and expensive noble metals such as rhodium(III), iridium(III), palladium(II), and ruthenium(II) are not required. The reaction proceeds via C - H activation, alkyne insertion, reductive elimination, and N - O activation.