18913-38-7

Usage

Synthesis Reference(s)

Tetrahedron Letters, 23, p. 2691, 1982 DOI: 10.1016/S0040-4039(00)87433-X

Upstream product

• 496-12-8 isoindoline 
• 108-24-7 acetic anhydride 
• 60-35-5 acetamide 
• 91-13-4 α,α'-dibromo-o-xylene 
• 75-36-5 acetyl chloride 
• 136918-14-4 phthalimide 
• 1334292-32-8 1-(2-(bromomethyl)phenyl)propan-2-one 
• 1334292-89-5 1-(2-(azidomethyl)phenyl)propan-2-one 

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).

ISOINDOLE DERIVATIVES

This invention relates to compounds of formula (I) or pharmaceutically acceptable salts thereof, a process of making these compounds, pharmaceutical compositions containing one or more of these compounds or their salts, and their use for the treatment of schizophrenia, bipolar disorder, or other central nervous system disorders.

New formation of 4,5,6,7-tetrahydroisoindoles

The high-yield syntheses of 4,5,6,7-tetrahydro-isoindoles from N-substituted isoindolines under palladium catalyzed hydrogenation conditions are reported. Mechanistic study with deuterated and saturated substrates show extensive H/D exchange and the essence of aromaticity in this transformation.