24464-35-5

Upstream product

• 119-65-3 isoquinoline 
• 23586-54-1 phenylthalium(III) di(trifluoroacetate) 
• 34784-04-8 5-bromoisoquinoline 
• 497-19-8 sodium carbonate 
• 98-80-6 phenylboronic acid 
• 108-95-2 phenol 
• 1125-60-6 isoquinolin-5-ylamine 
• 591-50-4 iodobenzene 
• 73183-34-3 bis(pinacol)diborane 
• 607-32-9 5-nitroisoquinoline 

Downstream Products

• 24464-38-8 5-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 223671-29-2 1-Chloro-5-phenylisoquinoline 

Relevant academic research and scientific papers

Practical and Asymmetric Reductive Coupling of Isoquinolines Templated by Chiral Diborons

We herein describe a chiral diboron-templated highly diastereoselective and enantioselective reductive coupling of isoquinolines that provided expedited access to a series of chiral substituted bisisoquinolines in good yields and excellent ee's under mild conditions. The method enjoys a broad substrate scope and good functional group compatibility. Mechanistic investigation suggests the reaction proceeds through a concerted [3,3]-sigmatropic rearrangement.

Iridium(III)-Catalyzed C(3)-H Alkylation of Isoquinolines via Metal Carbene Migratory Insertion

An Ir(III)-catalyzed C(3)-H alkylation of N-acetyl-1,2-dihydroisoquinolines with diverse acceptor-acceptor diazo compounds has been achieved under a single catalytic system via metal carbene migratory insertion. Moreover, further synthetic transformations of the alkylated products such as aromatization, selective decarboxylation, and decarbonylation lead to the formation of several synthetically viable isoquinoline derivatives having immense potentials.

Sterically hindered N-heterocyclic carbene/palladium(ii) catalyzed Suzuki-Miyaura coupling of nitrobenzenes

Palladium-catalyzed denitrative Suzuki coupling of nitroarenes using 2-aryl-5-(2,4,6-triisopropylphenyl)-2,3-imidazolylidene[1,5-a]pyridines as the ligands is described. The key to success is the use of the NHC ligands which show strong donating ability and suitable steric hindrance allowing the successful oxidative addition of Ar-NO2 bonds. Both aromatic and aliphatic boronic acids are tolerated, and a variety of biphenyls and alkylarenes were obtained in good to excellent yields.

Direct Arylation of Unactivated Alkanes with Heteroarenes by Visible-Light Catalysis

The functionalization of aliphatic C-H bonds is both a major challenge and a desirable goal in organic synthesis. Here, we describe the successful arylation of unactivated alkanes with heteroarenes by using iridium polypyridyl complexes as the photocatalyst and persulfate as the HAT catalyst precursor under visible-light irradiation. This reaction features good functional group tolerance and broad scope with regard to both alkane and heteroarene substrates (37 examples), which allows direct access to alkyl-substituted N-heteroarenes, a key structural motif in natural products and bioactive molecules.

Regioexhaustive Functionalization of the Carbocyclic Core of Isoquinoline: Concise Synthesis of Oxoaporphine Core and Ellipticine

A general and versatile strategy has been developed for the functionalization of the carbocyclic core of the isoquinoline. This regioexhaustive approach employs electrophilic halogenation as a toolbox methodology and delivers highly decorated intermediates that can be further elaborated toward medicinally relevant building blocks or natural products.

METHOD FOR PRODUCING AROMATIC COMPOUND

In a cross coupling reaction, in a case where a halogen atom is selected as the leaving group of the raw material compound, a harmful halogen waste forms as a by-product after the reaction, and disposal of the waste liquid is complicated and environmental burden is high. In a carbon-hydrogen activation cross coupling reaction which requires no halogen atom as the leaving group, although no halogen waste forms as a by-product, the reaction substrate is considerably restricted, and the reaction remains a limited molecular construction method. A method for producing an aromatic compound, which comprises subjecting an aromatic nitro compound and a boronic acid compound to a cross coupling reaction in the presence of a metal catalyst.

The Suzuki-Miyaura Coupling of Nitroarenes

Synthesis of biaryls via the Suzuki-Miyaura coupling (SMC) reaction using nitroarenes as an electrophilic coupling partners is described. Mechanistic studies have revealed that the catalytic cycle of this reaction is initiated by the cleavage of the aryl-nitro (Ar-NO2) bond by palladium, which represents an unprecedented elemental reaction.

CYANOPYRROLIDINES AS DUB INHIBITORS FOR THE TREATMENT OF CANCER

The present invention relates to novel compounds and method for the manufacture of inhibitors of deubiquitylating enzymes (DUBs). In particular, the invention relates to the inhibition of ubiquitin C- terminal hydrolase L1 (UCHL1) and ubiquitin C-terminal hydrolase 30 or ubiquitin specific peptidase 30 (USP30). The invention further relates to the use of DUB inhibitors in the treatment of cancer and conditions involving mitochondrial dysfunction. Compounds of the invention include compounds having the formula (I) or a pharmaceutically acceptable salt thereof, wherein R1,R2,R3,R4,R5,R6,R7,R8 and R9 are as defined herein.

Chemoselective One-Pot Synthesis of Functionalized Amino-azaheterocycles Enabled by COware

Functionalized bicyclic amino-azaheterocycles are rapidly accessed in a one-pot cross-coupling/reduction sequence enabled by the use of COware. Incompatible reagents are physically separated in a single reaction vessel to effect two chemoselective transformations - Suzuki-Miyaura cross-coupling and heteroarene reduction. The developed method allows access to novel heterocyclic templates, including semisaturated Hedgehog and dual PI3K/mTOR inhibitors, which show enhanced physicochemical properties compared to their unsaturated counterparts.

Preparation and catalytic activity of BINOL-derived silanediols

Enantiopure silanediols derived from BINOL are an innovative family of stereoselective hydrogen-bond donor (HBD) catalysts. Silanediols incorporated into a BINOL framework are attractive catalysts, as they are readily accessible and highly customizable. Structural modifications of the BINOL backbone affect the reactivity and selectivity of the silanediol catalysts in the additions of silyl ketene acetals to N-acyl isoquinolinium ions. The best results were obtained when the silanediol scaffold was substituted at the 4,4'- and 6,6'-positions. This report includes details regarding the properties of selected BINOL-based silanediol catalysts, including their acidities, binding constants, and X-ray crystal structures.