1198575-52-8

Upstream product

• 622-76-4 1-phenyl-1-butyne 
• 52260-22-7 N-chloro-1-phenylethan-1-imine 
• 618-36-0 rac-methylbenzylamine 
• 729-43-1 acetophenonazine 
• 4545-21-5 acetophenone p-toluenesulfonylhydrazone 
• 156605-56-0 1-phenylethan-1-one O-pivaloyl oxime 
• 98-86-2 acetophenone 
• 631-61-8 ammonium acetate 
• 13280-20-1 1-phenylethanimine 
• 32366-25-9 1-azidoethylbenzene 
• 13466-32-5 acetophenone dimethylhydrazone 
• 2142-70-3 2-iodoacetophenone 
• 613-91-2 acetophenone oxime 
• 1198575-54-0 (1E)-1-{2-[(1E)-1-benzylidenepropyl]phenyl}ethanone oxime 

Relevant academic research and scientific papers

Selective synthesis of alkynylated isoquinolines and biisoquinolines via RhIII catalyzed C-H activation/1,3-diyne strategy

Described herein is a convenient and highly selective synthesis of alkynylated isoquinolines and biisoquinolines from various aryl ketone O-pivaloyloxime derivatives and 1,3-diynes via rhodium-catalyzed C-H bond activation. In this transformations, alkynylated isoquinolines, 3,4′- and 3,3′-biisoquinolines could be obtained respectively through changing the reaction conditions. Mechanistic investigation revealed that the C-H activation of aryl ketone O-pivaloyloxime was the key step to this reaction.

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.

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.

Cp*Co(iii)-catalyzed annulation of azines by C-H/N-N bond activation for the synthesis of isoquinolines

Herein, an efficient, atom economic and external oxidant free approach has been disclosed for the synthesis of isoquinolines. Azines were employed for annulation reactions with alkynes via sequential C-H/N-N bond activation using an air-stable cobalt catalyst. The method takes advantage of the incorporation of both the nitrogen atoms of azines into the desired isoquinoline products, offering the highest atom economy. In addition, the developed protocol works under external oxidant as well as silver salt free conditions. Furthermore, the established methodology features a relatively broad substrate scope with high product yields and scalability up to the gram level.

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.

Cp*Co(III) catalyzed annulation of N-Cbz hydrazones for the redox-neutral synthesis of isoquinolines via C–H/N–N bond activation

A new cascade oxidative cyclization reaction of N-Cbz hydrazones with internal alkynes has been explored for the preparation of isoquinoline derivatives using Cp*CoIII-catalyst through C–H and N–N bond functionalization. N-Cbz hydrazones are ra

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

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

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.