3428-75-9Relevant academic research and scientific papers
Carbene-catalyzed aerobic oxidation of isoquinolinium salts: Efficient synthesis of isoquinolinones
Wang, Guanjie,Hu, Wanyao,Hu, Zhouli,Zhang, Yuxia,Yao, Wei,Li, Lin,Fu, Zhenqian,Huang, Wei
supporting information, p. 3302 - 3307 (2018/07/29)
A mild and environmentally friendly carbene-catalyzed aerobic oxidation of isoquinolinium salts was successfully realized. Accordingly, a diverse set of isoquinolinones and phenanthridinones was efficiently prepared in good to excellent yields. The mechanistic study indicates that the formation of an aza-Breslow intermediate is the crucial step in this transformation. This reaction features ambient air as the sole oxidant and oxygen source, a broad substrate scope, and excellent functional-group tolerance and proceeds under mild reaction conditions. Furthermore, a highly efficient synthesis of bioactive molecules and natural products including N-methylcrinasiadine, N-isopentylcrinasiadine, N-phenethylcrinasiadine, isoindolo[2,1-b]isoquinolin-5(7H)-one, PJ-34, rac-Gusanlung D, rosettacin, 8-oxopseudopalmatine and ilicifoline B was accomplished.
Evidence for a Radical Chain Mechanism for the Knabe Reaction of 1,2-Dihydro-2-methylpapaverine
Langhals, Elke,Langhals, Heinz,Ruechardt, Christoph
, p. 1436 - 1454 (2007/10/02)
A free radical chain mechanism is proposed for the Knabe reaction and the accompanying elimination reaction on account of their nonintegral reaction order and of successful inhibition experiments. 3,4-Dimethoxybenzyl radicals are the chain carrying species.Battersby's synthesis of N-methylpavine (19) from 1,2-dihydro-2-methylpapaverine (9) is dependent on the presence of formic acid as radical chain inhibitor.In the presence of inhibitors 1-benzyl-1,4-dihydro-2-methylisoquinolinium ions like 10 are persistent species whose chemistry can now be investigated.
CORYPALLINE AND O-METHYLCORYPALLINE, TWO ALKALOIDS FROM PAPAVER BRACTEATUM
Theuns, Hubert G.,Vlietstra, Edward J.,Salemink, Cornelis A.
, p. 247 - 250 (2007/10/02)
Two new Papaver alkaloids, corypalline and O-methylcorypalline, were identified from P. bracteatum.These alkaloids are considered as the biosynthetic precursors of N-methylcorydaldine in this plant.Key Word Index - Papaver bracteatum; Papaveraceae; alkaloids; tetrahydroisoquinolines; corypalline; O-methylcorypalline; biosynthetic pathway; 8-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline-7-ol; synthesis.
