6798-05-6

Usage

InChI:InChI=1/C10H11NO/c1-11-7-9-5-3-2-4-8(9)6-10(11)12/h2-5H,6-7H2,1H3

Upstream product

• 1334292-32-8 1-(2-(bromomethyl)phenyl)propan-2-one 
• 1334292-89-5 1-(2-(azidomethyl)phenyl)propan-2-one 
• 51052-00-7 1-(2-methylphenyl)acetone 

Downstream Products

• 1357254-44-4 C₁₆H₁₄FNO 
• 1357254-37-5 C₁₇H₁₉NO₂S 
• 1357254-46-6 C₁₇H₁₇NO 
• 1357254-36-4 C₁₇H₁₉N 
• 1357254-38-6 C₁₇H₁₉N 
• 1357254-39-7 C₁₉H₂₃N 
• 1357254-47-7 C₁₉H₂₁NO 
• 135182-06-8 4-(4-Methoxy-phenyl)-2-methyl-1,4-dihydro-2H-isoquinolin-3-one 
• 1357254-40-0 C₁₉H₁₈N₂ 
• 1357254-49-9 C₁₉H₁₆N₂O 
• 25771-98-6 4-(4-chlorophenyl)-2-methyl-1,2,3,4-tetrahydroisoquinoline 
• 1357254-43-3 C₁₆H₁₄ClNO 

Relevant academic research and scientific papers

Overcoming product inhibition in catalysis of the intramolecular Schmidt reaction

A method for carrying out the intramolecular Schmidt reaction of alkyl azides and ketones using a substoichiometric amount of catalyst is reported. Following extensive screening, the use of the strong hydrogen-bond-donating solvent hexafluoro-2-propanol was found to be consistent with low catalyst loadings, which ranged from 2.5 mol % for favorable substrates to 25 mol % for more difficult cases. Reaction optimization, broad substrate scope, and preliminary mechanistic studies of this improved version of the reaction are described.

In situ generation and intramolecular schmidt reaction of keto azides in a microwave-assisted flow format

Go with the flow! A method for conversion of keto halides to lactams by means of sequential azidation and intramolecular Schmidt reaction in a combined flow format is described (see scheme; MWI=microwave irradiation, TFA=trifluoroacetic acid).

Palladium-Catalyzed Inter- and Intramolecular α-Arylation of Amides. Application of Intramolecular Amide Arylation to the Synthesis of Oxindoles

2A palladium-catalyzed α-arylation of amides is reported. Intermolecular arylation of N,N-dimethylamides and lactams occurs using aryl halides, silylamide base, and a palladium catalyst. Intramolecular arylation of N-(2-halophenyl)amides occurs using alkoxide base and a palladium catalyst. The palladium catalyst was formed in situ from Pd(dba)2 (dba = trans,trans-dibenzylidene acetone) and BINAP (2,2′-bis(diphenylphosphino)-1,1′-binaphthalene). Although the intermolecular arylation of amides is less general than that reported previously for ketones, unfunctionalized and electron-rich aryl halides gave α-arylamides in 48-75% yield and N-methyl-α-phenylpyrrolidinone in 49% yield. These reactions provided the highest yields yet reported for regioselective amide arylations. Intramolecular amide arylation of 2-bromoanilides gave oxindoles in 52-82% yield. Mono- and disubstituted acetanilides gave 1,3-di- and 1,3,3-trisubstituted oxindoles. The use of dioxane, rather than THF, solvent was important for some of the amide arylations.