77901-22-5

Upstream product

• 21744-84-3 4-methyl-4H-benzo[1,4]oxazin-3-one 
• 100607-15-6 [2-(3-bromo-phenoxy)-ethyl]-methyl-amine 
• 133368-88-4 2-(N-methyl-o-anisidino)-ethanol 
• 106-93-4 ethylene dibromide 
• 611-24-5 o-(N-methylamino)phenol 
• 325147-44-2 N-(2-hydroxyethyl)-N-methyl-2-bromoaniline 
• 50-00-0 formaldehyd 
• 55339-51-0 2-allyloxy-1-nitrobenzene 
• 64-18-6 formic acid 
• 5735-53-5 1,4-benzoxazine 
• 95-55-6 2-amino-phenol 
• 273-53-0 benzoxazole 
• 5466-88-6 3,4-dihydro-3-oxo-2H-1,4-benzoxazine 
• 1878-87-1 2-nitrophenoxyacetic acid 

Downstream Products

• 892948-94-6 4-methyl-3,4-dihydro-2H-benzo[b][1,4]oxazine-6-sulfonyl chloride 
• 1291093-78-1 C₁₆H₁₃BrClNO₂ 
• 1291093-79-2 7-(5-bromo-2-chloro-benzyl)-4-methyl-3,4-dihydro-2H-benzo[1,4]oxazine 
• 1291093-80-5 (2S,3R,4S,5S,6R)-2-[4-chloro-3-(4-methyl-3,4-dihydro-2H-benzo[1,4]oxazin-7-ylmethyl)-phenyl]-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3,4,5-triol 
• 1291093-81-6 (2S,3R,4R,5S,6R)-2-[4-chloro-3-(4-methyl-3,4-dihydro-2H-benzo[1,4]oxazin-7-ylmethyl)-phenyl]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol 
• 519054-54-7 4-methyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydro-2H-1,4-benzoxazine 
• 1256256-24-2 4-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine 
• 1583286-76-3 C₁₅H₂₂BNO₃ 
• 141103-94-8 (4-Methyl-3,4-dihydro-2H-benzo[1,4]oxazin-7-yl)-methanol 
• 154264-95-6 7-bromo-4-methyl-3,4-dihydro-2H-benzo[b][1,4]oxazine 
• 141103-93-7 4-methyl-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-carbaldehyde 

Relevant academic research and scientific papers

Visible-Light-Enabled Direct Decarboxylative N-Alkylation

The development of efficient and selective C?N bond-forming reactions from abundant feedstock chemicals remains a central theme in organic chemistry owing to the key roles of amines in synthesis, drug discovery, and materials science. Herein, we present a dual catalytic system for the N-alkylation of diverse aromatic carbocyclic and heterocyclic amines directly with carboxylic acids, by-passing their preactivation as redox-active esters. The reaction, which is enabled by visible-light-driven, acridine-catalyzed decarboxylation, provides access to N-alkylated secondary and tertiary anilines and N-heterocycles. Additional examples, including double alkylation, the installation of metabolically robust deuterated methyl groups, and tandem ring formation, further demonstrate the potential of the direct decarboxylative alkylation (DDA) reaction.

Iron-Catalyzed Selective N-Methylation and N-Formylation of Amines with CO2

We herein describe an efficient iron-catalyzed selective N-methylation and N-formylation of amines with CO2 and silane using mono-phosphine as ligand. With commercially available [CpFe(CO)2]2 as catalyst, Fe-catalyzed methylation of amines was achieved with triphenylphosphine as a ligand. Using tributylphosphine as a ligand, Fe-catalyzed formylation of amines was realized at a lower temperature. The method was successfully applied in the late-stage methylation and formylation of drug molecules containing amine moiety. (Figure presented.).

Controlled Reduction of Tertiary Amides to the Corresponding Alcohols, Aldehydes, or Amines Using Dialkylboranes and Aminoborohydride Reagents

Dialkylboranes and aminoborohydrides are mild, selective reducing agents complementary to the commonly utilized amide reducing agents, such as lithium aluminum hydride (LiAlH4) and diisobutylaluminum hydride (DIBAL) reagents. Tertiary amides were reduced using 1 or 2 equiv of various dialkylboranes. The reduction of tertiary amides required 2 equiv of 9-borabicyclo[3.3.1]nonane (9-BBN) for complete reduction to give the corresponding tertiary amines. One equivalent of sterically hindered disiamylborane reacts with tertiary amides to afford the corresponding aldehydes. Aminoborohydrides are powerful and selective reducing agents for the reduction of tertiary amides. Lithium dimethylaminoborohydride and lithium diisopropylaminoborohydride are prepared from n-butyllithium and the corresponding amine-borane. Chloromagnesium dimethylaminoborohydride (ClMg+[H3B-NMe2]-, MgAB) is prepared by the reaction of dimethylamine-borane with methylmagnesium chloride. Solutions of aminoborohydride reduce aliphatic, aromatic, and heteroaromatic tertiary amides to give the corresponding alcohol, amine, or aldehyde depending on the steric requirement of the tertiary amide and the aminoborohydride used.

Metal-free catalyst for the chemoselective methylation of amines using carbon dioxide as a carbon source

N-methylation of amines is an important step in the synthesis of many pharmaceuticals and has been widely applied in the preparation of other key intermediates and chemicals. Therefore, the development of efficient methylation methods has attracted considerable attention. In this respect, carbon dioxide is an attractive C1 building block because it is an abundant, renewable, and nontoxic carbon source. Consequently, we developed a highly chemoselective, metal-free catalytic system that operates under ambient conditions for the N-methylation of amines. The methylation of amines with CO2 as C1 source and Ph2SiH2 as reducing agent was achieved with an N-heterocyclic carbene (NHC) as the catalyst. The catalyst is tolerant toward a variety of functional groups (including esters and ethers, nitro, nitrile, and carbonyl groups, and unsaturated C-C bonds); the reaction uses commercially available reagents and can be performed on a gram scale.

GLYCOSIDE DERIVATIVE AND USES THEREOF

This invention relates to compounds represented by formula (I): wherein the variables are defined as herein above, which are useful for treating diseases and conditions mediated by the sodium D-glucose co-transporter (SGLT), e.g. diabetes. The invention also provides methods of treating such diseases and conditions, and compositions etc. for their treatment.

GLYCOSIDE DERIVATIVE AND USES THEREOF

This invention relates to compounds represented by formula (I) wherein the variables are defined as herein above, which are useful for treating diseases and conditions mediated by the sodium D-glucose co-transporter (SGLT), e.g. diabetes. The invention also provides methods of treating such diseases and conditions, and compositions etc. for their treatment.

GLYCOSIDE DERIVATIVES AND USES THEREOF

This invention relates to compounds represented by formula (I): wherein the variables are defined as herein above, which are useful for treating diseases and conditions mediated by the sodium D-glucose co-transporter (SGLT), e.g. diabetes. The invention also provides methods of treating such diseases and conditions, and compositions etc. for their treatment

Glycoside Derivatives and Uses Thereof

This invention relates to compounds represented by formula (I): wherein the variables are defined as herein above, which are useful for treating diseases and conditions mediated by the sodium D-glucose co-transporter (SGLT), e.g. diabetes. The invention also provides methods of treating such diseases and conditions, and compositions etc. for their treatment.

ALKYL-SUBSTITUTED 3' COMPOUNDS HAVING 5-HT6 RECEPTOR AFFINITY

The present disclosure provides compounds having affinity for the 5-HT6 receptor which are of the formula (I): wherein R1, R2, Ar, m and n are as defined herein. The disclosure also relates to methods of preparing such compounds, compositions containing such compounds, and methods of use thereof.

CONDENSED HETEROCYCLIC COMPOUNDS HAVING 5-HT6 RECEPTOR AFFINITY

The present disclosure provides compounds having affinity for the 5-HT6 receptor which are of the formula (I) wherein R1, A, B, D, E, G, Q, Ar, n, m, and p are as defined herein. The disclosure also relates to methods of preparing such compounds, compositions containing such compounds, and methods of use thereof.