72785-34-3

Upstream product

• 5392-10-9 2-bromo-4,5-dimethoxybenzaldehyde 
• 74-89-5 methylamine 
• 89525-44-0 N-methyl-3,4-dimethoxy-6-bromobenzalimine 

Downstream Products

• 131326-85-7 2-[(2-Bromo-4,5-dimethoxy-benzyl)-methyl-amino]-1-(4-methoxy-phenyl)-ethanone 
• 89505-95-3 [(C₆H₂(OCH₃)2CH₂N(CH₃)HPd(P(C₆H₅)3)Br)] 
• 1326343-87-6 C₁₅H₂₂BrNO₂ 
• 140420-12-8 1-[(3,4-Dimethoxy-benzyl)-methyl-amino]-2-(4-methoxy-phenyl)-hexan-2-ol 
• 131326-87-9 dimethoxy-6,7 hydroxy-4 (methoxy-4' phenyl)-4 methyl-2 tetrahydroisoquinoleine 
• 131326-95-9 2-[(3,4-Dimethoxy-benzyl)-methyl-amino]-1-(4-methoxy-phenyl)-ethanone 
• 23330-76-9 6,7-dimethoxy-4-(4-methoxyphenyl)-2-methyl-1, 2, 3, 4-tetrahydroisoquinoline 

Relevant academic research and scientific papers

Development of an intramolecular aryne ene reaction and application to the formal synthesis of (±)-crinine

A general and high yielding annulation strategy for the synthesis of various carbo- and heterocycles, based on an intramolecular aryne ene reaction is described. It was found that the geometry of the olefin is crucial to the success of the reaction, with exclusive migration of the trans-allylic-H taking place. Furthermore, the electronic nature of the aryne was found to be important to the success of the reaction. Deuterium labeling studies and DFT calculations provided insight into the reaction mechanism. The data suggests a concerted asynchronous transition state, resembling a nucleophilic attack on the aryne. This strategy was successfully applied to the formal synthesis of the ethanophenanthridine alkaloid (±)-crinine.

Intramolecular aryne-ene reaction: Synthetic and mechanistic studies

Although the chemistry of arynes is well developed, some challenges still remain. The ene reaction of arynes has not gained widespread use in synthesis as a result of poor yields and selectivity. A general, high yielding and selective intramolecular aryne-ene reaction is described providing various benzofused carbo- and heterocycles. Mechanistic data is presented, and a rationale for the resulting stereochemistry is discussed.

A convenient synthesis of 4-substituted 1,2,3,4-tetrahydroisoquinolin-4-ols by a novel intramolecular Barbier reaction and by an insertion reaction: Reaction scope and limitations

4-Substituted 1,2,3,4-tetrahydroisoquinolin-4-ols were prepared from N-(2-iodobenzyl)phenacylamines by an intramolecular Barbier reaction with butyllithium and by an insertion reaction with zerovalent nickel. The scope and limitations of these reactions were discussed.

PALLADIUM ASSISTED ORGANIC REACTIONS. VII. THE PREPARATION OF CYCLOPALLADATED PRIMARY AND SECONDARY BENZYLAMINES

A new method is described for the preparation of cyclopalladated benzylamines, involving the reaction of the ortho-bromobenzylamines with bis(dibenzylideneacetone)palladium(0).By using this method cyclopalladated complexes of simple primary and secondary benzylamines have been obtained for the first time.These complexes have been fully characterised as either the monomeric bromo(benzylamine-6-C,N)triphenylphosphinepalladium(II) derivatives or as the corresponding acetyl-acetonates. 1H and 13C NMR spectral data have been obtained and, in most cases, full assignments have been made.