7661-60-1

Usage

Uses

Used in Pharmaceutical Industry:
Isoquinoline, 1-ethylis used as a key intermediate in the synthesis of various drugs due to its versatile chemical properties and ability to form stable derivatives.
Used in Antihypertensive Drug Production:
Isoquinoline, 1-ethylis used as an active pharmaceutical ingredient for the production of antihypertensive drugs, helping to regulate blood pressure and manage hypertension.
Used in Anti-inflammatory Agent Development:
Isoquinoline, 1-ethylis utilized in the development of anti-inflammatory agents, contributing to the reduction of inflammation and alleviation of associated symptoms.
Used in Muscle Relaxant Formulation:
Isoquinoline, 1-ethylis incorporated into muscle relaxant formulations, aiding in the relief of muscle spasms and associated pain.
Used as a Building Block in Chemical Synthesis:
Beyond its direct pharmaceutical applications, Isoquinoline, 1-ethylserves as a fundamental building block in the synthesis of various other chemical compounds, highlighting its importance in both the pharmaceutical and chemical industries.

InChI:InChI=1/C11H11N/c1-2-11-10-6-4-3-5-9(10)7-8-12-11/h3-8H,2H2,1H3

Upstream product

• 119-65-3 isoquinoline 
• 19026-44-9 1-ethenylisoquinoline 
• 41173-70-0 1-ethyl-3,4-dihydro-isoquinoline 
• 75-03-6 ethyl iodide 
• 19493-44-8 1-chloroisoquinoline 
• 925-90-6 ethylmagnesium bromide 
• 76143-79-8 (1-phenyl-propylamino)-acetaldehyde diethylacetal 
• 80781-07-3 2-(5-phenyl-1-tetrazolyl)isoquinoline 
• 83-33-0 inden-1-one 
• 113605-01-9 1-Cyano-1-ethyl-1H-isoquinoline-2-carboxylic acid phenyl ester 
• 65-85-0 benzoic acid 
• 53600-01-4 2-crotonyl-1-cyano-1,2-dihydroisoquinoline 
• 53600-03-6 1-cyano-1,2-dihydro-2-(3,3-dimethylacryloyl)isoquinoline 
• 1721-93-3 1-methylisoquinoline 

Relevant academic research and scientific papers

Radical C?H Acylation of Nitrogen Heterocycles Induced by an Aerobic Oxidation of Aldehydes

An aerobic radical approach for the synthesis of unsymmetrical heteroaryl ketones is described herein. The reaction involves cross-dehydrogenative coupling between aldehydes and heteroaromatic bases with molecular oxygen (O2). The key aspect of the method is the generation of reactive acyl radical via homolytic activation of aldehyde C?H bond using O2 as the sole oxidant. The reaction has a good substrate scope with respect to aldehydes and functionalized nitrogen heterocycles. Based on our mechanistic studies, a radical chain pathway is suggested for the reaction. A synthetic application of the method is demonstrated in the formal synthesis of natural alkaloid (±) angustureine.

Selective functionalization of methane, ethane, and higher alkanes by cerium photocatalysis

With the recent soaring production of natural gas, the use of methane and other light hydrocarbon feedstocks as starting materials in synthetic transformations is becoming increasingly economically attractive, although it remains chemically challenging. W

Dioxygen-Mediated Decarbonylative C-H Alkylation of Heteroaromatic Bases with Aldehydes

An operationally simple and economical method for the direct alkylation of heteroaromatic bases employing readily available aldehydes as alkyl radical precursors and molecular oxygen as a reagent is presented. This simple transformation demonstrates a broad substrate scope with respect to aldehydes and nitrogen heterocycles, enabling the introduction of several medicinally important yet challenging alkyl moieties, such as ethyl, isopropyl, tert-butyl, and cyclohexyl to the different classes of heterocyclic bases in good to excellent yields. A simple method for the direct alkylation of heteroaromatic bases with aldehydes as inexpensive alkyl radical precursors and molecular oxygen as a reagent is presented. This transformation demonstrates a broad substrate scope with respect to aldehydes and nitrogen heterocycles, enabling the introduction of various alkyl moieties to heterocyclic bases (>40 examples) in good to excellent yields.

Alcohols as alkylating agents in heteroarene C-H functionalization

Redox processes and radical intermediates are found in many biochemical processes, including deoxyribonucleotide synthesis and oxidative DNA damage. One of the core principles underlying DNA biosynthesis is the radical-mediated elimination of H2O to deoxygenate ribonucleotides, an example of 'spin-centre shift', during which an alcohol C-O bond is cleaved, resulting in a carbon-centred radical intermediate. Although spin-centre shift is a well-understood biochemical process, it is underused by the synthetic organic chemistry community. We wondered whether it would be possible to take advantage of this naturally occurring process to accomplish mild, non-traditional alkylation reactions using alcohols as radical precursors. Because conventional radical-based alkylation methods require the use of stoichiometric oxidants, increased temperatures or peroxides, a mild protocol using simple and abundant alkylating agents would have considerable use in the synthesis of diversely functionalized pharmacophores. Here we describe the development of a dual catalytic alkylation of heteroarenes, using alcohols as mild alkylating reagents. This method represents the first, to our knowledge, broadly applicable use of unactivated alcohols as latent alkylating reagents, achieved via the successful merger of photoredox and hydrogen atom transfer catalysis. The value of this multi-catalytic protocol has been demonstrated through the late-stage functionalization of the medicinal agents, fasudil and milrinone.

Rh-catalyzed sequential oxidative C-H activation/annulation with geminal-substituted vinyl acetates to access isoquinolines

The concise synthesis of 3-substituted or non-C3-substituted isoquinolines through Rh-catalyzed sequential oxidative C-H activation/annulation with geminal-substituted vinyl acetates was developed with good functional group tolerance. The protocol was successfully applied to the total synthesis of the natural product papaverine.

Trimethyl borate/magnesium halide complex-induced one-pot homologation reactions of isoquinoline with dialkyl-TMP-zincate

Novel one-pot homologation reactions of isoquinoline with lithium dialkyl-TMP-zincate?2MgBrCl/trimethyl borate are described. 1-Alkylisoquinolines (2, 3A, 4A, 5A, 6, and 7) and 1-alkyl-3,4- dihydroisoquinolines (3B, 4B, and 5B) are easily prepared under t

Isoxazolinoisoquinoline Heterocycles via Solid-Phase Reinsert and Suzuki Reactions

A traceless solid-phase synthesis strategy has been developed that delivers novel isoxazolinoisoquinoline heterocycles. The process consists of solid-phase Reissert formation (isoquinoline → I), Suzuki coupling lithiation, and subsequent C1-alkylation (I → II), and exo-olefin selective 1,3-dipolar nitrile oxide cycloaddition followed by Reissert hydrolysis (II → III) to liberate the targeted heterocycle.

Reissert Compound Studies. LXV. Praparation of Reissert Compounds Derived from α,β-Unsaturated Acid Chlorides

Reissert compounds derived from α,β-unsaturated acid chlorides were prepared.The conjugate base obtained from these Reissert compounds exhibited the following carbanion reactions: 1) Alkylation, 2) Condensation with benzaldehyde, 3) Rearrangement to give dimeric compounds rather than simple rearranged compounds.In the case of alkylated isoquinoline Reissert compounds, the attempted rearrangement led to ring annellated amines.

The Reaction of N-Carboalkoxy Reissert Analogs with Carboxylic Acids

The reaction of N-carboalkoxy Reissert analogs in the presence of carboxylic acids yields the corresponding ester and heterocyclic base.Use of methoxy substituted benzoic acids yields, instead of the ester, the respective anhydride.Amides can also be prepared in a similar fashion.