55676-25-0Relevant articles and documents
Palladium-catalyzed regiocontrolled internal heteroarylation of electron-rich olefins with heteroaryl halides
Xu, Dan,Liu, Zhihua,Tang, Weijun,Xu, Lijin,Hyder, Zeynab,Xiao, Jianliang
scheme or table, p. 6104 - 6107 (2009/04/04)
A highly efficient palladium-catalyzed Heck coupling reaction of heteroaryl halides with electron-rich vinyl ether and hydroxyalkyl vinyl ethers is described. It was found that the choice of solvent, ligand, and reaction temperature had a fundamental influence on the regioselectivity and reactivity of the reaction, and the combination of Pd(OAc)2 and DPPF in ethylene glycol led to the most effective catalytic system. Under these conditions, a variety of heteroaryl halides reacted very quickly with electron-rich olefins to afford exclusively the branched products in good to excellent yields without employing triflates, halide scavengers, or ionic liquids.
Syntheses of an Antipsychotic Pyrroloisoquinoline from Areca Alkaloids
Coffen, David L.,Hengartner, Urs,Katonak, David A.,Mulligan, Mary E.,Burdick, David C.,et al.
, p. 5109 - 5113 (2007/10/02)
2,6-Dimethyl-3-ethyl-4,4a,5,6,7,8,8a,9-octahydro-4a,8a-trans-1H-pyrroloisoquinolin-4-one, a conformationally defined antipsychotic agent of current clinical interest, can be synthesized in a two-step, single-pot process from arecoline, a commercially available member of the areca alkaloid group.The yield is diminished by the competing, base-induced rearrangement of arecoline to 1,3-dimethyl-2-pyridone.This problem can be circumvented by using arecolone as the starting material.A convenient synthesis of arecolone from 3-acetylpyridine is described.A modifiedform of the Neber rearrangement was used to prepare 2-amino-3-pentanone hydrochloride for use in the Knorr pyrrole synthesis step of the process.Two isomeric pyrroloisoquinolines produced as minor byproducts were isolated and characterized as the cis- and trans- isomers.Characterization of the latter included an X-ray crystal structure determination.