40692-45-3

Usage

Uses

Used in Pharmaceutical Industry:
4-Benzyl-3,4-dihydroisoquinolin-1(2H)-one is used as a potential drug candidate for the treatment of neurological disorders due to its demonstrated biological activities and potential pharmacological effects.
Used in Organic Synthesis:
4-Benzyl-3,4-dihydroisoquinolin-1(2H)-one serves as a valuable building block in organic synthesis, contributing to the development of new compounds with therapeutic potential.
Used in Medicinal Chemistry Research:
4-Benzyl-3,4-dihydroisoquinolin-1(2H)-one is utilized in the field of medicinal chemistry for further research and development, given its interesting structure and properties that warrant exploration for novel therapeutic applications.

Upstream product

• 300-57-2 allylbenzene 
• 61650-22-4 N-(pivaloyloxy)benzamide 
• 495-18-1 Benzohydroxamic acid 
• 1293990-69-8 N-((tert-butoxycarbonyl)oxy)benzamide 

Relevant academic research and scientific papers

Ligand design for Rh(iii)-catalyzed C-H activation: An unsymmetrical cyclopentadienyl group enables a regioselective synthesis of dihydroisoquinolones

We report the regioselective synthesis of dihydroisoquinolones from aliphatic alkenes and O-pivaloyl benzhydroxamic acids mediated by a Rh(iii) precatalyst bearing sterically bulky substituents. While the prototypical Cp ligand provides product with low s

Rhodium(III) Complex with a Bulky Cyclopentadienyl Ligand as a Catalyst for Regioselective Synthesis of Dihydroisoquinolones through C?H Activation of Arylhydroxamic Acids

Catalytic reaction of arylhydroxamic acids with alkenes represents a convenient method for preparation of biologically active dihydroisoquinolones. Here, the rhodium(III) complex [(C5H2tBu2CH2tBu)RhCl2]2, which allows one to carry out such reactions with high regioselectivity to obtain 4-substituted dihydroisoquinolones in 72–97 % yields, is described. The regioselectivity is provided by the bulky cyclopentadienyl ligand of the catalyst, which is formed through a [2+2+1] cyclotrimerization of tert-butylacetylene. The catalytic reaction tolerates various distant functional groups in alkenes, but is inhibited by bulky (e.g., tBu) or strongly coordinating (e.g., imidazolyl) substituents. Some of the prepared dihydroisoquinolones effectively inhibit growth of phytopathogenic fungi.

Rhodium(III)-catalyzed heterocycle synthesis using an internal oxidant: Improved reactivity and mechanistic studies

Directing groups that can act as internal oxidants have recently been shown to be beneficial in metal-catalyzed heterocycle syntheses that undergo C-H functionalization. Pursuant to the rhodium(III)-catalyzed redox-neutral isoquinolone synthesis that we recently reported, we present in this article the development of a more reactive internal oxidant/directing group that can promote the formation of a wide variety of isoquinolones at room temperature while employing low catalyst loadings (0.5 mol %). In contrast to previously reported oxidative rhodium(III)-catalyzed heterocycle syntheses, the new conditions allow for the first time the use of terminal alkynes. Also, it is shown that the use of alkenes, including ethylene, instead of alkynes leads to the room temperature formation of 3,4-dihydroisoquinolones. Mechanistic investigations of this new system point to a change in the turnover limiting step of the catalytic cycle relative to the previously reported conditions. Concerted metalation-deprotonation (CMD) is now proposed to be the turnover limiting step. In addition, DFT calculations conducted on this system agree with a stepwise C-N bond reductive elimination/N-O bond oxidative addition mechanism to afford the desired heterocycle. Concepts highlighted by the calculations were found to be consistent with experimental results.