24464-39-9Relevant academic research and scientific papers
Regioexhaustive Functionalization of the Carbocyclic Core of Isoquinoline: Concise Synthesis of Oxoaporphine Core and Ellipticine
Horváth, Dániel Vajk,Domonyi, Frigyes,Palkó, Roberta,Lomoschitz, Andrea,Soós, Tibor
, p. 2181 - 2190 (2018/03/21)
A general and versatile strategy has been developed for the functionalization of the carbocyclic core of the isoquinoline. This regioexhaustive approach employs electrophilic halogenation as a toolbox methodology and delivers highly decorated intermediates that can be further elaborated toward medicinally relevant building blocks or natural products.
Ruthenium-catalyzed chemo-and enantioselective hydrogenation of isoquinoline carbocycles
Jin, Yushu,Makida, Yusuke,Uchida, Tatsuya,Kuwano, Ryoichi
, p. 3829 - 3839 (2018/04/14)
A chemoselective hydrogenation of isoquinoline carbocycles was achieved by using the catalyst prepared from Ru(methallyl)2(cod) and trans-chelate chiral ligand PhTRAP. The unique chemoselectivity achieved in this hydrogenation could be ascribed to the trans-chelation of the chiral ligand. The procedure for preparing the catalyst strongly affects the reproducibility of the carbocycle hydrogenation. Various 5-, 6-, 7-, and 8-substituted isoquinolines were selectively hydrogenated at their carbocycles to afford 5,6,7,8-tetrahydroisoquinolines as major products in high yields with moderate or good enantioselectivities. Some mechanistic studies suggested that the stereogenic center was created during the initial addition of H2 to the aromatic ring in the hydrogenation of 5-substituted isoquinolines. In other words, the stereochemical control was accompanied by the dearomatization.
Ready access to 6-alkyl, 6-phenyl, 5,6-dialkyl, and 5-alkyl-6-phenyl substituted 1,2,3,4-tetrahydroisoquinolines
Nussbaumer,Dechat
, p. 1047 - 1055 (2007/10/03)
Readily available bicyclic enone precursors were used in a novel strategy for the synthesis of 6-mono- and 5,6-disubstituted tetrahydroisoquinolines (alkyl and phenyl in position 6, hydrogen and methyl in position 5). After 1,2-addition of the respective
Versatile and Efficient Synthesis of Aryl-1,2,3,4-tetrahydroisoquinolines: Nickel(II) Phosphine Ligand Catalyzed Coupling of Arylmagnesium Halides to Haloisoquinolines
Pridgen, Lendon N.
, p. 1289 - 1291 (2007/10/02)
Dichloronickel(II) (dppp) was used as catalyst to prepare some previously unreported arylisoquinolines 3, which were in turn hydrogenated to aryl-1,2,3,4-tetrahydroisoquinolines 2.This procedure is the most direct and ef
