131372-97-9

Usage

Chemical class

Isoquinoline

Molecular structure

Complex three-dimensional structure with a phenyl group attached to the 1-position of the isoquinoline ring system

Potential use

Medicinal chemistry, specifically in neuropharmacology for potential neuroprotective and antidepressant effects

Importance in synthetic chemistry

Interesting target for developing new methodologies for its synthesis

Biological activities

Potential for neuroprotective and antidepressant effects

Applications

Drug discovery and development

Unique feature

Complex structure and potential biological activities

Upstream product

• 98-81-7 1-bromovinylbenzene 
• 131372-95-7 1-Bromo-3,4-dihydronaphthalene-2-carboxaldehyde N,N-dimethylhydrazone 
• 529-34-0 3,4-dihydronaphthalene-1(2H)-one 
• 117582-62-4 1-bromo-2-formyl-3,4-dihydronaphthalene 

Relevant academic research and scientific papers

Preparation of 1-substituted-3,4-dihydronaphthalene-2-carboxaldehyde N,N-dimethylhydrazones by palladium(0) coupling, and their electrocyclic ring closure

1-Bromo-3,4-dihydronaphthalene-2-carboxaldehyde 2 has been converted by three methods, each involving halogen-metal exchange and palladium(0) catalysed cross coupling, into N,N-dimethylhydrazones of 1-aryl- and 1-vinyl-3,4-dihydronaphthalene-2- carboxaldehydes. The N,N-dimethylhydrazone 10 of the aldehyde 2 undergoes efficient bromine-lithium exchange with butyllithium, as does 2-bromobenzaldehyde N,N-dimethylhydrazone 17. The dimethylhydrazones of 1-vinyl-3,4-dihydronaphthalene-2-carboxaldehydes were not isolated by underwent electrocyclic ring closure followed by loss of dimethylamine in solution to give 5,6-dihydrobenz[f]isoquinolines. 1-Aryl-3,4-dihydronaphthalene-2- carboxaldehyde N,N-dimethylhydrazones also cyclised in the same way when subjected to vapour phase pyrolysis.

SYNTHESIS OF FUSED PYRIDINES BY ELECTROCYCLIC RING CLOSURE OF ALDEHYDE NN-DIMETHYLHYDRAZONES

3,4-Dihydronaphthalene-2-carboxaldehyde NN-dimethylhydrazones bearing an alkenyl or aryl substituent at the 1-position undergo thermal electrocyclic ring closure followed by the loss of dimethylamine, giving fused pyridines.