1599-33-3

Upstream product

• 98-88-4 benzoyl chloride 
• 109-05-7 2-Methylpiperidin 
• 109-06-8 α-picoline 
• 65-85-0 benzoic acid 
• 3197-42-0 (S)-2-methylpiperidine 
• 100-52-7 benzaldehyde 
• 1000789-28-5 C₁₂H₁₆ClNS 
• 120986-91-6 B(OC₂H₅)2(CH₂)4CH(N₃)CH₃ 
• 5119-88-0 2-methylpiperidine hydrochloride 

Downstream Products

• 13729-76-5 N-Benzoyl-2-methyl-4-piperidon 
• 627-96-3 1,5-dibromohexane 
• 100-47-0 benzonitrile 
• 54305-90-7 1,5-dichloro-hexane 
• 92041-66-2 6-benzoylamino-5-methylpentanoic acid 
• 1019351-96-2 (2-hydroxy-phenyl)-(2-methyl-piperidin-1-yl)-methanone 

Relevant academic research and scientific papers

Diboron-Catalyzed Dehydrative Amidation of Aromatic Carboxylic Acids with Amines

Tetrakis(dimethylamido)diboron and tetrahydroxydiboron are herein reported as new catalysts for the synthesis of aryl amides by catalytic condensation of aromatic carboxylic acids with amines. The developed protocol is both simple and highly efficient over a broad range of substrates. This method thus represents an attractive approach for the use of diboron catalysts in the synthesis of amides without having to resort to stoichiometric or additional dehydrating agents.

Deactivation mechanisms of iodo-iridium catalysts in chiral amine racemization

The homogenous, [IrCp?I2]2, SCRAM catalyst (1) is active in the racemization of chiral amines. NMR, kinetic and structural mechanistic studies have determined the cause of catalyst deactivation to occur when ammonia or methylamine are liberated by hydrolysis or aminolysis of the intermediate imine, which tightly coordinate to the iridium centre to block turnover. Control of moisture and substrate concentration can suppress deactivation, whilst partial reactivation of spent catalyst was identified using hydroiodic acid.

DECONSTRUCTIVE FUNCTIONALIZATION METHODS AND COMPOUNDS

Disclosed herein, inter alia, are deconstructive functionalization methods and compounds made using the same.

Tris(o-phenylenedioxy)cyclotriphosphazene as a Promoter for the Formation of Amide Bonds between Aromatic Acids and Amines

The atom-efficient formation of amide bonds has emerged as a top-priority research field in organic synthesis, as amide bonds constitute the backbones of proteins and represent an important structural motif in drug molecules. Currently, the increasing demand for novel discoveries in this field has focused substantial attention on this challenging subject. Herein, the degradable 1,3,5-triazo-2,4,6-triphosphorine (TAP) motif is presented as a new condensation system for the dehydrative formation of amide bonds between diverse combinations of aromatic carboxylic acids and amines. The underlying reaction mechanism was investigated, and potential catalyst intermediates were characterized using 31 P NMR spectroscopy and ESI mass spectrometry.

Cross-Dehydrogenating Coupling of Aldehydes with Amines/R-OTBS Ethers by Visible-Light Photoredox Catalysis: Synthesis of Amides, Esters, and Ureas

A straightforward synthesis of amides, ureas, and esters is reported by visible-light cross-dehydrogenating coupling (CDC) of aldehydes (or amine carbaldehydes) and amines/R-OTBS ethers by photoredox catalysis. The reaction is found to be general and high yielding. A plausible mechanistic pathway has been proposed for these transformations and is supported by appropriate controlled experiments.

N-tosyl-(S)-prolyl chloride in kinetic resolution of racemic heterocyclic amines

The kinetic resolution of racemic heterocyclic amines via acylation with N-tosyl-(S)-prolyl chloride was systematically investigated. It was established that racemic mixtures of aromatic amines could be resolved with high efficiency, while the acylation of 2- and 3-methylpiperidines occurred with low diastereoselectivity. A method for the preparation of enantiomerically pure (3R)-7,8-difluoro-3-methyl-3,4-dihydro-2H-[1,4]benzoxazine was developed.

5-Exo versus 6-Endo cyclization of primary aminyl radicals: An experimental and theoretical investigation

(Chemical Equation Presented) The cyclization of neutral primary pent-4-enylaminyl radicals was investigated experimentally and theoretically. Unlike the corresponding secondary aminyl radicals, primary pent-4-enylaminyl radicals underwent efficient cyclization to afford the pyrrolidine and/or piperidine products in good to high yields. While the simple pent-4-enylaminyl radical gave predominately the 5-exo cyclization product, 4-chloropent-4- enylaminyl radicals led to the formation of the corresponding 6-endo cyclization products in excellent regioselectivity. Theoretical calculations revealed that the 5-exo cyclization rate of primary aminyl radicals is about 3-4 orders of magnitude higher than that of secondary aminyl radicals.

Solid-supported cyclohexane-1,3-dione (CHD): A "capture and release" reagent for the synthesis of amides and novel scavenger resin

A three-step synthesis of cyclohexane-1,3-dione (CHD) resin 6 on polystyrene resin is described. Resin 6 was used to prepare an amide library of high purity by microwave-assisted serial "capture and release" and can be recycled for this purpose. High-loading CHD resin 10 was also shown to scavenge allyl cations in solution.

Synthesis of azetidine, pyrrolidines and piperidine by intramolecular cyclization of ω-Azidoboranes.

This paper describes the development of efficient routes to azetidine, pyrrolidines and piperidines by creation of a carbon-nitrogen bond.Two complementary syntheses of these heterocycles were studied : the cyclization of ω-azidoboronic esters by treatment with boron trichloride, and the one pot hydroboration of an ω-azidoalkene and intramolecular reductive alkylation.The scope and limitations of these two promising approaches are reported.Keywords: azides / boronic esters / boranes / intermolecular cyclization / azetidine / pyrrolidine / piperidine / pyrrolizidine

A Convenient Synthetic Route to Methylated Silacyclohexanes

The von Braun degradation of substituted piperidines is a general and economical route to a variety of substituted primary and secondary α,ω-dibromopentanes.Grignard ring closure procedures have been carried out with seven different dibromopentanes in moderate to good yields.Ring closures with MeClSiCl2 lead to product mixtures which are appreciably enriched in one isomer, affording a convenient entry into a variety of derivatives which can be used for stereochemical studies.Assignment of structures based on 1H NMR and mass spectral fragmentation patterns is discussed