65185-61-7

Upstream product

• 98-88-4 benzoyl chloride 
• 529-34-0 3,4-dihydronaphthalene-1(2H)-one 
• 6729-50-6 2,3,4,5-tetrahydro-1H-2-benzazepin-1-one 
• 100-39-0 benzyl bromide 
• 107733-72-2 6-Oxo-6H-pyran-2-carboxylic acid benzyl-pent-4-enyl-amide 
• 54436-58-7 N-benzylpent-4-en-1-amine 
• 107742-26-7 2-benzyl-2,3,4,5,5a,6-hexahydro-1H-2benzazepin-1-one 
• 92885-62-6 anti-2'-benzyl-1,2,3,4-tetrahydronaphthalene-1-spiro-3'-oxaziridine 

Relevant academic research and scientific papers

Synthesis of Medium-Ring-Sized Benzolactams by Using Strong Electrophiles and Quantitative Evaluation of Ring-Size Dependency of the Cyclization Reaction Rate

Benzolactams with medium-sized rings were synthesized via the electrophilic aromatic substitution reaction of carbamoyl cations (R1R2N+═C═O) in good to high yields without dilution. These reactions were utilized to quantitatively examine the extent of retardation of medium-sized ring formation, compared to five- or six-membered ring formation. The order of reaction rates of formation of cyclic benzolactams is six- > five- > seven- > eight- > nine-membered ring at 25 °C. The present reaction provides a route to eight- A nd nine-membered benzolactams.

Straightforward α-Amino Nitrile Synthesis Through Mo(CO)6-Catalyzed Reductive Functionalization of Carboxamides

The selective reduction of amides into an intermediate hemiaminal catalyzed by Mo(CO)6 together with the inexpensive and easy to handle TMDS (1,1,3,3-tetramethyldisiloxane) as reducing agent, followed by subsequent trapping of the hemiaminal with a cyanide source, allows for the straightforward synthesis of α-amino nitriles. The methodology presented here, displays high levels of chemoselectivity allowing for the reduction of amides in the presence of functional groups such as ketones, imines, aldehydes, and acids, which affords a simple route for the synthesis of α-amino nitriles with a broad scope of functionalities in high yields. Furthermore, the applicability of this methodology is demonstrated by scale up experiments and by derivatization of the target compounds into synthetically interesting products. The selective cyanation is successfully applied in late stage functionalizations of amide containing drugs and prolinol derivatives.

Iridium-Catalyzed Reductive Strecker Reaction for Late-Stage Amide and Lactam Cyanation

A new iridium-catalyzed reductive Strecker reaction for the direct and efficient formation of α-amino nitrile products from a broad range of (hetero)aromatic and aliphatic tertiary amides, and N-alkyl lactams is reported. The protocol exploits the mild and highly chemoselective reduction of the amide and lactam functionalities using IrCl(CO)[P(C6H5)3]2 (Vaska's complex) in the presence of tetramethyldisiloxane, as a reductant, to directly generate hemiaminal species able to undergo substitution by cyanide upon treatment with TMSCN (TMS=trimethylsilyl). The protocol is simple to perform, broad in scope, efficient (up to 99 % yield), and has been successfully applied to the late-stage functionalization of amide- and lactam-containing drugs, and naturally occurring alkaloids, as well as for the selective cyanation of the carbonyl carbon atom linked to the N atom of proline residues within di- and tripeptides.

Photochemistry of 2'-substituted 1,2,3,4-Tetrahydronaphthalene-1-spiro-3'-oxaziridines. Variable-temperature 1H Nuclear Magnetic Resonance Spectroscopy of 1-Substituted 1,3,4,5-Tetrahydro-2H-1-benzazepin-2-ones

The lack of regioselectivity of photorearrangement of the title spiro-oxaziridines in wich the N-substituent is syn to the aromatic ring suggests that the first formed N-O-bond-cleaved species has a significant lifetime allowing rotation (inversion) to complete with rearrangement.The energy barrier to ring inversion of the title tetrahydro-1-benzazepin-2-ones is significantly influenced by the steric interaction between the N-substituent and the peri hydrogen atom.

Intramolecular "Diene-Regenerable" Diels-Alder Reaction of 2-Pyrone-6-carboxamides. Preparation and Reaction of Fused 1,3-Cyclohexadiene Systems

The 2-pyrone-6-carboxamides, prepared from 2-pyrone-6-carbonyl chloride and substituted allylamine, undergo intramolecular Diels-Alder reaction spontaneously to give 3a,4,5,7a-tetrahydro-1-oxoisoindoline-5,7a-carbolactones, which regenerate the diene moie

PHOTOCHEMISTRY OF N-SUBSTITUTED SPIROOXAZIRIDINES DERIVED FROM TETRALONE-1

Photolyses of spirooxaziridines from tetralone-1 in which the N-substituent is syn to the aromatic ring are less regioselective than their anti-isomers suggesting the first formed N-O bond cleaved species has a significant life time.