26906-15-0Relevant academic research and scientific papers
α-C-H/N-H Annulation of Alicyclic Amines via Transient Imines: Preparation of Polycyclic Lactams
Chen, Weijie,Seidel, Daniel
supporting information, p. 3729 - 3734 (2021/05/31)
Polycyclic lactams are prepared in a single operation from o-toluamides and cyclic amines in a process that involves transient cyclic imines, species that are conveniently obtained in situ from the corresponding lithium amides and simple ketone oxidants. Imines thus generated, such as 1-pyrroline and 1-piperideine, engage lithiated o-toluamides in a facile annulation process. Undesired side reactions such as imine deprotonation and o-toluamide dimerization are suppressed through the judicious choice of reaction conditions.
Synthesis of 12-oxobenzo[c]phenanthridinones and 4-substituted 3-arylisoquinolones via Vilsmeier-Haack reaction
Khadka, Daulat Bikram,Yang, Su Hui,Cho, Suk Hee,Zhao, Chao,Cho, Won-Jea
, p. 250 - 261 (2012/01/05)
Vilsmeier-Haack reaction on 3-arylisoquinolones resulted in versatile 4-formylated 3-arylisoquinolones that were further derivatized into 12-oxobenzo[c]phenanthridinones, 4-alkoxymethyl-3-arylisoquinolones, 3-aryl-4-phenoxymethylisoquinolones, 4-aminometh
Total synthesis of 8-oxypseudopalmatine and 8-oxypseudoberberine via ring-closing metathesis
Van, Hue Thi My,Yang, Su Hui,Khadka, Daulat Bikram,Kim, Yong-Chul,Cho, Won-Jea
experimental part, p. 10142 - 10148 (2010/02/27)
Concise synthesis of 8-oxypseudopalmatine and 8-oxypseudoberberine has been achieved using ruthenium-catalyzed ring-closing metathesis (RCM) as the key step, in which the RCM substrates, 3-arylisoquinolinones, were prepared by lithiated cycloaddition reac
Asymmetric synthesis of 3-substituted dihydro-2H-isoquinolin-1-ones, dihydro- and tetrahydroisoquinolines via 1,2-addition/ring closure
Enders, Dieter,Braig, Volker,Boudou, Marine,Raabe, Gerhard
, p. 2980 - 2990 (2007/10/03)
The asymmetric synthesis of 3-substituted dihydro-2H-isoquinolin-1-ones, dihydro- and tetrahydroisoquinolines is described. The key operation is a tandem 1,2-addition/ring closure sequence employing lithiated ortho-toluamides and aldehyde SAMP- or RAMP-hydrazones as substrates, followed by N-N bond cleavage to remove the auxiliary. Moderate to good yields and high enantiomeric excesses (ee = 85-99%) are reached.
Novel sparteine-mediated enantio-dichotomic formal synthesis of (R)-(-)- and (S)-(+)-curcuphenol
Kimachi,Takemoto
, p. 2700 - 2704 (2007/10/03)
High and opposite enantiodiscriminations were observed between tertiary amides and secondary amides in the sparteine-mediated lateral metalation-allylation of 2-ethyl-m-toluamide derivatives (2a, 2e). The results described above have been applied for the formal synthesis of both enantiomers of curcuphenol. The brief mechanistic studies suggested that stereoinformation was introduced after the deprotonation step.
