77894-41-8Relevant academic research and scientific papers
Tandem Reaction Approaches to Isoquinolones from 2-Vinylbenzaldehydes and Anilines via Imine Formation-6π-Electrocyclization-Aerobic Oxidation Sequence
Lee, Jiyeon,Kim, Hun Young,Oh, Kyungsoo
, p. 474 - 478 (2020/01/21)
Two distinctive transition-metal-promoted aerobic oxidation protocols have been developed for the synthesis of isoquinolones from 2-vinylbenzaldehydes and aniline derivatives. Thus, the one-pot tandem reaction sequence of imine formation, thermal 6π-electrocyclization, followed by either Cu(OAc)2-mediated or Pd(OAc)2-catalyzed aerobic oxidation protocol allowed the ready access to isoquinolone derivatives. The control experiments revealed that the 1,2-dihydroisoquinoline intermediates from the 6π-electrocyclization of 1-azatrienes were aerobically oxidized to isoquinolones in the presence of either Cu(OAc)2 or Pd(OAc)2 catalyst.
Synthesis of 2,4-disubstituted isoquinolin-1(2H)-ones based on reactions of α-substituted 2-lithio-β-methoxystyrenes with isocyanates
Kobayashi, Kazuhiro,Hayashi, Kazutaka,Nam, Changeng,Fukamachi, Shuhei,Konishi, Hisatoshi
, p. 1225 - 1231 (2008/12/20)
An efficient method for the preparation of 2,4-disubstituted isoquinolin-1(2H)-ones is described. The reaction of α-substituted 2-lithio-β-methoxystyrenes, generated by treating α-substituted 2-bromo-β-methoxystyrenes with butyilithium, with isocyanates yields the corresponding α-substituted 2-(2-methoxyvinyl)benzamide derivatives, which in turn are transformed into 2,4-disubstituted isoquinolin-1(2H)-ones on treatment with a catalytic amount of concentrated hydriodic acid.
A New Route to Diarylisoquinolones
Dodsworth, David J.,Pia-Calcagno, Maria,Ehrmann, E. Ursula,Quesada, Andres M.,Nunez S., Oswaldo,Sammes, Peter G.
, p. 1453 - 1458 (2007/10/02)
The lithium salts derived from position 3 of phthalides react with Schiff's bases to form a mixture of cis- and trans-2,3-disubstituted 4-hydroxy-3,4-dihydro-1(2H)-isoquinolones, the former isomer predominating.Acid-catalysed dehydration of the alcohols gives 2,4-disubstituted 1(2H)-isoquinolones, as a result of aryl group migration, whilst the cis-isomers, with methanesulphonyl chloride-pyridine as dehydrating agent, produce the 2,3-disubstituted 1(2H)-isoquinolones.
A ONE-STEP ROUTE TO 4-HYDROXY-2,3-DIARYL-3,4-DIHYDRO-1(2H)-ISOQUINOLONES
Dodsworth, David J.,Caliagno, Maria-Pia,Ehrmann, Ursula E.
, p. 5075 - 5078 (2007/10/02)
A new procedure for the synthesis of 2,3-diaryl-3,4-dihydro-4-hydroxy-1(2H)-isoquinolones is described in which the cis-isomer predominates.Dehydration leads to 2,4-diarylisocarbostyrils.
