Category: isoquinoline

Aravindan, Narasingan published the artcileA Short Total Synthesis of Benzophenanthridine Alkaloids via a Rhodium(III)-Catalyzed C-H Ring-Opening Reaction, Quality Control of 86-51-1, the main research area is rhodium catalyst diastereoselective regioselective ring opening oxidation; benzophenanthridine alkaloid total synthesis.

The biol. important naturally available benzophenanthridines were prepared efficiently in three steps with overall good yields. A new synthetic methodol. involving a rhodium(III) catalyzed redox-neutral ring-opening of 7-azabenzonorbornadienes with aromatic aldoximes is developed to synthesize the target mols. The developed C-H ring-opening reaction is highly diastereoselective and compatible with various sensitive functional group substituted aromatic aldoximes as well as substituted 7-azabenzonorbornadienes. The ring-opening products were transformed into highly sensitive 13,14-dehydrobenzo phenanthridine derivatives by HCl hydrolysis. Subsequently, 13,14-dehydrobenzophenanthridines were converted into biol. important benzophenanthridine alkaloids in the presence of DDQ. A possible reaction mechanism was proposed for the C-H ring-opening reaction and supported by the deuterium labeling studies.

Journal of Organic Chemistry published new progress about Benzophenanthridine alkaloids Role: PRP (Properties), SPN (Synthetic Preparation), PREP (Preparation). 86-51-1 belongs to class isoquinoline, name is 2,3-Dimethoxybenzaldehyde, and the molecular formula is C9H10O3, Quality Control of 86-51-1.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Hong Nguyen, Thi Anh published the artcileMetal-free, Direct Acetoxylation of Arenes, Recommanded Product: 1,3-Dimethoxybenzene, the main research area is arene acetic acid regioselective acetoxylation; aryl acetate preparation.

A metal-free, direct acetoxylation reaction using sodium nitrate under an anhydrous environment of trifluoroacetic acid, acetic acid and acetic anhydride was reported. Arenes (31 examples), with oxidation potentials (Eox, in V vs SCE) lower than benzene (2.48 V), were acetoxylated with good yields and regioselectivity. A stepwise, single electron-transfer mechanism was proposed.

Organic Letters published new progress about Acetoxylation (regioselective). 151-10-0 belongs to class isoquinoline, name is 1,3-Dimethoxybenzene, and the molecular formula is C8H10O2, Recommanded Product: 1,3-Dimethoxybenzene.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Zeng, Qian published the artcileCopper-catalyzed carbene/alkyne metathesis terminated with the Buchner reaction: synthesis of dihydrocyclohepta[b]indoles, Computed Properties of 104-01-8, the main research area is aminophenylpropynyl diazophenylacetate copper tandem carbene alkyne metathesis Buchner reaction; cycloheptaindolyl phenylfuranone regioselective preparation.

A copper-catalyzed selective cascade reaction of alkyne-tethered diazo compounds was reported for the direct and efficient construction of dihydrocyclohepta[b]indole skeletons under mild reaction conditions. A vinyl copper carbene was the key intermediate, which was generated in-situ via carbene/alkyne metathesis (CAM) and terminated with the Buchner reaction.

Organic & Biomolecular Chemistry published new progress about Alcohols, propargyl Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 104-01-8 belongs to class isoquinoline, name is 4-Methoxyphenylacetic acid, and the molecular formula is C9H10O3, Computed Properties of 104-01-8.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

De Smet, Gilles published the artcileSelective Nickel-Catalyzed Hydrodeacetoxylation of Aryl Acetates, Recommanded Product: 1,3-Dimethoxybenzene, the main research area is aromatic alc magnesium catalyst acetoxylation; aryl acetate preparation nickel catalyst chemoselective hydrodeacetoxylation green chem; anisole preparation; Aryl Acetates; C−O Bond Activation; Hydrodeacetoxylation; Nickel Catalysis; Renewable Resources.

Ni-catalyzed hydrodeacetoxylation of aryl acetates (Ar-OAc) with HBpin in a green carbonate solvent selectively delivered the corresponding deoxygenated arenes (ArH). The method was also applicable to highly challenging guaiacyl and syringyl acetates, leaving -OMe groups intact without arene reduction Renewable 4-propylguaiacol obtained from pine could also be transformed without significant loss in yield vs. oil derived feedstock. The observed chemoselectivity for Ar-OAc vs. ArO-Ac bond cleavage was rationalized based on mechanistic experiments and DFT calculations ArOH side-product formation was attributed to direct competitive Ni-catalyzed reduction of the C=O bond. Hydrodeacyloxylation of a set of aryl alkanoates featured interesting chemoselectivity with a dramatic influence of the length and structure of the alkyl chain on catalysis.

Angewandte Chemie, International Edition published new progress about Aromatic compounds Role: SPN (Synthetic Preparation), PREP (Preparation). 151-10-0 belongs to class isoquinoline, name is 1,3-Dimethoxybenzene, and the molecular formula is C8H10O2, Recommanded Product: 1,3-Dimethoxybenzene.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Virumbrales, Cintia published the artcileGold(I)-catalyzed nucleophilic cyclization of β-monosubstituted o-(alkynyl)styrenes: A combined experimental and computational study, Quality Control of 151-10-0, the main research area is alkynyl styrene nucleophile gold catalyst diastereoselective regioselective nucleophilic cyclization; alkoxymethyl indene preparation; hydroxymethyl indene preparation; diphenylmethyl indene preparation.

The stereospecific gold(I)-catalyzed nucleophilic cyclization of β-monosubstituted o-(alkynyl)styrenes to produce C-1 functionalized 1H-indenes, including challenging substrates and nucleophiles such as β-(cyclo)alkyl-substituted o-(alkynyl)styrenes and a variety of alcs. as well as selected electron-rich aromatics, is reported. DFT calculations support the stereochem. outcome of the process that involves the formation of a key cyclopropyl gold carbene intermediate through a regiospecific 5-endo cyclization.

Organic & Biomolecular Chemistry published new progress about Alkenynes Role: PRP (Properties), RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 151-10-0 belongs to class isoquinoline, name is 1,3-Dimethoxybenzene, and the molecular formula is C8H10O2, Quality Control of 151-10-0.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Murugesan, Kathiravan published the artcilePhotoredox-Catalyzed Site-Selective Generation of Carbanions from C(sp3)-H Bonds in Amines, Computed Properties of 5961-59-1, the main research area is deuterium tritium labeled amine preparation; amine photoredox catalyst deuterium tritium labeling.

Herein, activation of a C(sp3)-H bond in the α-position to an amine via a carbanion intermediate was described. In the presence of several α-amine sites, only one specific position was selectively activated. Applying this protocol, the proposed carbanion intermediate was effectively trapped with different electrophiles such as deuterium (D+), tritium (T+), or carbonyl compounds compiling over 50 examples. Further, this methodol. was used to install deuterium or tritium in different drug-derivatives (>10 drugs) at a selected position in a late-stage functionalization. In addition, the protocol was suitable for a gram-scale synthesis, and a detailed mechanistic investigation was carried out to support our hypothesis.

ACS Catalysis published new progress about Amides Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 5961-59-1 belongs to class isoquinoline, name is 4-Methoxy-N-methylaniline, and the molecular formula is C8H11NO, Computed Properties of 5961-59-1.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Biswas, Nandita published the artcileRu-Catalyzed Selective Catalytic Methylation and Methylenation Reaction Employing Methanol as the C1 Source, Recommanded Product: 4-Methoxy-N-methylaniline, the main research area is methylated compound green preparation; phenylethanol methanol methylation ruthenium catalyst; naphthol methanol methylation ruthenium catalyst; amine methanol methylation ruthenium catalyst.

The activity of the acridine-derived SNS-Ru pincer for the activation of methanol to apply it as a C1 building block in different reactions was explored. Catalytic system showed great success toward the β-C(sp3)-methylation reaction of 2-phenylethanols to provide good to excellent yields of the methylated products RCH(CH3)CH2OH [R = Ph, 4-FC6H4, 2-thienyl, etc.]. The mechanistic details, kinetic progress and temperature-dependent product distribution, which revealed the slow and steady generation of in situ formed aldehyde, was the key factor to get the higher yield of the β-methylated product. To establish the environmental benefit of this reaction, green chem. metrics were calculated Furthermore, dimerization of 2-naphthol via methylene linkage to obtain methylated products I [R1 = H, 3-MeO, 6-Ph, etc.] and formation of N-methylation of amine were also described in this study, which offers a wide range of substrate scope with a good to excellent yield of methylated products R2NHCH3 [R2 = (CH2)7CH3, Ph, 2-BrC6H4, etc.].

Journal of Organic Chemistry published new progress about Amines Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 5961-59-1 belongs to class isoquinoline, name is 4-Methoxy-N-methylaniline, and the molecular formula is C8H11NO, Recommanded Product: 4-Methoxy-N-methylaniline.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Biswas, Nandita published the artcileRu-Catalyzed Selective Catalytic Methylation and Methylenation Reaction Employing Methanol as the C1 Source, Safety of 4-Methoxyphenylacetic acid, the main research area is methylated compound green preparation; phenylethanol methanol methylation ruthenium catalyst; naphthol methanol methylation ruthenium catalyst; amine methanol methylation ruthenium catalyst.

The activity of the acridine-derived SNS-Ru pincer for the activation of methanol to apply it as a C1 building block in different reactions was explored. Catalytic system showed great success toward the β-C(sp3)-methylation reaction of 2-phenylethanols to provide good to excellent yields of the methylated products RCH(CH3)CH2OH [R = Ph, 4-FC6H4, 2-thienyl, etc.]. The mechanistic details, kinetic progress and temperature-dependent product distribution, which revealed the slow and steady generation of in situ formed aldehyde, was the key factor to get the higher yield of the β-methylated product. To establish the environmental benefit of this reaction, green chem. metrics were calculated Furthermore, dimerization of 2-naphthol via methylene linkage to obtain methylated products I [R1 = H, 3-MeO, 6-Ph, etc.] and formation of N-methylation of amine were also described in this study, which offers a wide range of substrate scope with a good to excellent yield of methylated products R2NHCH3 [R2 = (CH2)7CH3, Ph, 2-BrC6H4, etc.].

Journal of Organic Chemistry published new progress about Amines Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 104-01-8 belongs to class isoquinoline, name is 4-Methoxyphenylacetic acid, and the molecular formula is C9H10O3, Safety of 4-Methoxyphenylacetic acid.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Das, Kuhali published the artcileManganese-Catalyzed Anti-Markovnikov Hydroamination of Allyl Alcohols via Hydrogen-Borrowing Catalysis, Formula: C11H12O3, the main research area is amino alc preparation regioselective chemoselective; allyl alc amine anti Markovnikov hydroamination manganese catalyst.

In this article, a selective formal anti-Markovnikov hydroamination of allyl alcs. RCH=C(R1)C(R2)OH (R = H, Me, n-Pr, pent-4-en-1-yl; R1 = H, Me; R2 = H, Me, Ph, furan-2-yl, etc.) is presented. It enables the versatile synthesis of valuable γ-amino alc. building blocks e.g., 3-(methyl(phenyl)amino)propan-1-ol. A phosphine-free Earth’s abundant manganese(I) complex catalyzed the reaction under hydrogen-borrowing conditions. A vast range of amines such as pyrrolidine, aniline, 1H-indoline, morpholine, etc. drug mols., and natural product derivs e.g., I. underwent successful hydroamination with primary and secondary allylic alcs. with excellent functional group tolerance. The catalysis could be performed on a gram scale and has been applied for the synthesis of drug mols. The mechanistic studies revealed the metal-ligand bifunctionality as well as hemilability of the ligand backbone as the key design principle for the success of this catalysis.

ACS Catalysis published new progress about Amines Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 1205-17-0 belongs to class isoquinoline, name is 2-Methyl-3-(3,4-methylenedioxyphenyl)propionaldehyde, and the molecular formula is C11H12O3, Formula: C11H12O3.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Das, Kuhali published the artcileManganese-Catalyzed Anti-Markovnikov Hydroamination of Allyl Alcohols via Hydrogen-Borrowing Catalysis, Synthetic Route of 5961-59-1, the main research area is amino alc preparation regioselective chemoselective; allyl alc amine anti Markovnikov hydroamination manganese catalyst.

In this article, a selective formal anti-Markovnikov hydroamination of allyl alcs. RCH=C(R1)C(R2)OH (R = H, Me, n-Pr, pent-4-en-1-yl; R1 = H, Me; R2 = H, Me, Ph, furan-2-yl, etc.) is presented. It enables the versatile synthesis of valuable γ-amino alc. building blocks e.g., 3-(methyl(phenyl)amino)propan-1-ol. A phosphine-free Earth’s abundant manganese(I) complex catalyzed the reaction under hydrogen-borrowing conditions. A vast range of amines such as pyrrolidine, aniline, 1H-indoline, morpholine, etc. drug mols., and natural product derivs e.g., I. underwent successful hydroamination with primary and secondary allylic alcs. with excellent functional group tolerance. The catalysis could be performed on a gram scale and has been applied for the synthesis of drug mols. The mechanistic studies revealed the metal-ligand bifunctionality as well as hemilability of the ligand backbone as the key design principle for the success of this catalysis.

ACS Catalysis published new progress about Amines Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 5961-59-1 belongs to class isoquinoline, name is 4-Methoxy-N-methylaniline, and the molecular formula is C8H11NO, Synthetic Route of 5961-59-1.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem