131373-01-8

Usage

Structure

A derivative of isoquinoline
With a trimethylsilyl group attached to the carbon atom in the 1-position

Stability

Stable compound

Usage

Building block in organic synthesis
For the creation of more complex molecules

Applications

Medicinal chemistry and drug discovery research
As an intermediate in the synthesis of various pharmaceuticals and organic compounds

Additional applications

Development of novel materials and chemical technologies

Upstream product

• 131372-98-0 3,4-Dihydro-1-<(1'-trimethylsilyl)ethenyl>naphthalene-2-carboxaldehyde 
• 13683-41-5 1-bromo-1-(trimethylsilyl)ethene 
• 89822-46-8 (1-Vinyl)trimethylsilylzinc chloride 
• 529-34-0 3,4-dihydronaphthalene-1(2H)-one 
• 117582-62-4 1-bromo-2-formyl-3,4-dihydronaphthalene 
• 57-14-7 N,N-Dimethylhydrazine 

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.