55857-35-7Relevant articles and documents
Synthesis of a family of 3-alkyl- or 3-aryl-substituted 1,2-dihydroquinazolinium salts and their isomerization to 4-iminium-1,2,3,4- tetrahydroquinolines
Vicente, Jose,Chicote, Maria Teresa,Martinez-Martinez, Antonio Jesus,Bautista, Delia,Jones, Peter G.
supporting information; experimental part, p. 2279 - 2285 (2011/05/02)
A straightforward synthesis of substituted 1,2-dihydroquinazolinium triflates (3) is reported by reaction of 2-imino-substituted anilines with a range of carbonyl compounds in the presence of triflic acid via intermediate iminium salts. Similar reactions
Preparation of axially chiral quinolinium salts related to NAD+ models: New investigations of these biomimetic models as 'chiral amide-transferring agents'
Leleu, Stephane,Papamicael, Cyril,Marsais, Francis,Dupas, Georges,Levacher, Vincent
, p. 3919 - 3928 (2007/10/03)
The general purpose of this work is to investigate the potential of biomimetic NAD+ models as 'nucleophile-transferring agents' with the ultimate motivation to develop new synthetic tools. This first report focuses on the preparation of an axially chiral quinolinium salt 8. A preliminary investigation of these NAD+ analogues as 'chiral amide-transferring agents' is reported herein. The synthesis of the desired quinolinium salt 8 was first attempted via a Friedlaender approach. Given the poor reproducibility of this first synthetic route, a second strategy making use of an intramolecular nickel-catalyzed coupling was developed with success, furnishing the quinolinium salt 8 in 12% overall yield. The potential of the quinolinium salt 8 as a 'chiral amide-transferring agent' was then investigated. Regioselective 1,4-addition of benzylamine and piperidine produced, respectively, adducts 18a and 18b with high diastereoselectivity (de >95%). The resulting 'chiral masked-amide' 18b was reacted with various activated aryl esters affording the corresponding atropisomeric amide 20 with modest atropenantioselectivity (ee = 2-20%).