7661-37-2

Upstream product

• 91417-00-4 1-propyl-3,4-dihydroisoquinoline 
• 119-65-3 isoquinoline 
• 123-72-8 butyraldehyde 
• 71-23-8 propan-1-ol 
• 6283-13-2 N-(2-phenylethyl)butanamide 
• 76143-81-2 (2,2-Diethoxy-ethyl)-(1-phenyl-butyl)-amine 
• 772-92-9 C₉H₇BF₃N 
• 61190-02-1 (2,2-Diethoxy-ethyl)-[1-phenyl-meth-(Z)-ylidene]-amine 
• 64-04-0 phenethylamine 

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.

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.

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.

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

A ONE-POT ISOQUINOLINE SYNTHESIS BY CYCLODEHYDROGENATION OF BENZYLAMINOACETALS WITH CHLOROSULFONIC ACID

A direct preparation of the fully aromatized isoquinolines (3a-l) by the cyclodehydrogenation of benzylamnoacetals (2a-l) with chlorosulfonic acid is described.Comparing the behavior of chlorosulfonic acid with that of sulfuric acid toward 1,2-dihydroisoquinoline, it is able to be suggested that benzylaminoacetals were cyclized first to 1,2-dihydroisoquinolines, subsequently, dehydrogenated to the fully aromatized isoquinolines by the hydride abstraction with ClSO3H.Subtitution by a larger R3 group than isopropyl in the acetal ArCH(R3)NHCH2CH(OEt)2, interfered this second step, so the corresponding isoquinolines could not be obtained.