77988-87-5Relevant academic research and scientific papers
Diprotonative stabilization of ring-opened carbocationic intermediates: conversion of tetrahydroisoquinoline to triarylmethanes
Kurouchi, Hiroaki
, p. 8313 - 8316 (2020/08/17)
Superacid-promoted conversion of tetrahydroisoquinolines to triarylmethanes via tandem reactions of C-N bond scission, Friedel-Crafts alkylation, C-O bond scission, and electrophilic aromatic amidation was developed. Dication formation was important for stabilizing the ring-opened carbocationic intermediate, which is a new role for diprotonation in reaction mechanisms. This journal is
New synthesis of isoquinoline and 3,4-dihydroisoquinoline derivatives
Kobayashi, Kazuhiro,Shiokawa, Taiyo,Omote, Hiroki,Hashimoto, Kenichi,Morikawa, Osamu,Konishi, Hisatoshi
, p. 1126 - 1132 (2007/10/03)
A simple and efficient synthesis of isoquinoline and 3,4- dihydroisoquinoline derivatives is described. 1-Alkyl-(or aryl)isoquinoline and 1-isoquinolinamine derivatives were obtained by intramolecular cyclization of 2-(2-methoxyethenyl) benzonitriles initiated by the addition of alkyl(or aryl)lithiums and lithium dialkylamides to the nitrile carbons, respectively. Synthesis of 4-aryl-3,4-dihydroisoquinolines was achieved by reactions of 2-(1-arylethenyl)benzonitriles with organolithiums, followed by aqueous workup. Treatment of the reaction mixtures with electrophiles prior to aqueous workup allowed the synthesis of 4,4-disubstituted 3,4-dihydroisoquinolines.
The mechanism of the Bischler-Napieralski Reaction
Nagubandi, Sreeramulu,Fodor, G.
, p. 1457 - 1463 (2007/10/02)
The Bischler-Napieralski dihydroisoquinoline synthesis was proven to occur via imidoyl chlorides and the corresponding nitrilium salt.Two-step process required much milder conditions (20 degC - 50 degC) compared to drastic classical conditions of refluxing at 100 degC - 200 degC.The Bischler-Napieralski reaction is shown to share a common intermediate with two other well-known reactions: the von Braun and the Ritter reactions
