13797-31-4Relevant academic research and scientific papers
New synthetic methodology for construction of the 3,4-dihydroisoquinolinone skeleton: A key structure for isoquinoline alkaloids
Muejde, Berk,Oezcan, Sevil,Balci, Metin
, p. 407 - 410 (2012/04/10)
We hereby report a new method for preparation of 3,4-dihydroisoquinolin- 1(2H)-one as well as isoquinolin-1(2H)-one skeleton starting from the methyl 2-(3-methoxy-3-oxopropyl)benzoate. The ester functionality, adjacent to the methylene, was regiospecifically converted to the desired acyl azide. The isocyanate was transformed into the monoisocyanate by Curtius rearrangement followed by trapping with aniline. The formed urea derivative was cyclized with NaH to give a 3,4-dihydroisoquinolin-1(2H)-one derivative. Incorporation of a double bond into the six-membered ring followed by removal of the substituent resulted in the formation of isoquinolin-1(2H)-one skeleton.
Characterization of the two fundamental conformations of benzoylureas and elucidation of the factors that facilitate their conformational interchange
Lessene, Guillaume,Smith, Brian J.,Gable, Robert W.,Baell, Jonathan B.
supporting information; experimental part, p. 6511 - 6525 (2010/03/02)
(Figure Presented) The ability of the benzoylurea core to mimic R helices relies on its ability to forman intramolecular hydrogen bond. The conformational behavior of benzoylureas is investigated in depth in this study via the use of NMR, IR, X-ray, and computational analysis. The results show that the closed conformation maintained by an intramolecular hydrogen bond is favored in most of the cases studied except when steric and electronic effects combined with a solvent possessing a high hydrogen bond accepting ability, such asDMSO, are involved. The study highlights the propensity for benzoylureas to switch conformation depending on the environment of the molecule for a particular set of substituents. We anticipate that our summary of the phenomenon of internal hydrogen bonding and its analysis may further serve as a useful reference source for future workers in this area.
