171920-10-8Relevant academic research and scientific papers
Efficient synthesis of the azabicyclo[3.3.1]nonane ring system in the alkaloid methyllycaconitine using bis(alkoxymethyl)alkylamines as aminoalkylating agents in a double Mannich reaction
Brimble, Margaret A.,Brocke, Constanze
, p. 2385 - 2396 (2007/10/03)
The double Mannich reaction of cyclic β-keto esters with bis-(alkoxymethyl)alkylamines provides an efficient and versatile method for the construction of azabicyclo[3.3.1]nonanes and azabicyclo[3.2.1]octanes. The optimum conditions for efficient reaction involve use of the activator trichloromethylsilane in acetonitrile as solvent at ambient temperature. The utility of this synthetic method is further demonstrated by the facile synthesis of several AE ring analogues 39, 42 of the alkaloid methyllycaconitine by appendage of the key N-(methylsuccininimido)anthranilate pharmacophore to the N-(3-phenylpropyl)-substituted double Mannich adducts 18, 27. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.
The Synthesis of 2-Arylmethyltetrahydroisoquinolines from Bis(Aminol) Ethers Involving Two Iminium Salt Intermediates
Heaney, Harry,Papageorgiou, George,Wilkins, Robert F.
, p. 10737 - 10750 (2007/10/02)
The bis(aminol) ether derived from 3,4-dimethoxy-β-phenylethylamine, methanol, and formaldehyde reacts with trichloromethylsilane to afford an equilibrium mixture of N-chloromethyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline and its related iminium chloride.Interaction with electron rich aromatic compounds afford good yields of N-arylmethyl derivatives, including sendaverine methyl ether.Reactions of the bis(amino) ether in the presence of the aromatic substrate allows the formation of the N-arylmethyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline derivatives in a one pot reaction.
