The synthesis of 2′,2′-bis-benzylisoquinolines and their cytostatic activities

Abstract

The synthesis of 2',2'-bis-benzylisoquinolines and their cytostatic activities The synthesis of 2',2'-bis-benzylisoquinolines and their cytostatic activities

Oxidative C–H Homodimerization of Phenylacetamides

“…The dimeric phenylacetamides can display a variety of functionality and have been used as TM ligands 5 and precursors to biologically active biaryls. 6 Existing synthetic routes to these products use classic Ullmann coupling of aryl iodides with copper catalysis. 6,7 The reaction proved successful for electron-neutral and -rich arenes, whereas electron-poor substrates were unreactive.…”

“…6 Existing synthetic routes to these products use classic Ullmann coupling of aryl iodides with copper catalysis. 6,7 The reaction proved successful for electron-neutral and -rich arenes, whereas electron-poor substrates were unreactive. The parent (2b and 2c), Me (2e, 2f, and 2g), and OMe (2d) substituted compounds were all formed in moderate to good yields, but p-fluoro-and p-chlorophenylacetamides were unreactive under the conditions.…”

The synthesis of carbon linked bis-benzylisoquinolines using Mizoroki–Heck and Sonagashira coupling reactions

“…Our approach to the target molecules 2 (alkene linker) was based on a Mizoroki-Heck coupling reaction of racemic N-trifluoroacetyl-2'-iodonorlaudanosine 4 10 and the racemic alkenes rac-5 and rac-6. The alkenes rac-5 and rac-6 were efficiently prepared from rac-4 using Stille coupling reactions (Scheme 1).…”

An alkaloid-like 3-azabicyclo[3.3.1]non-3-ene library obtained from the bridged Ritter reaction

“…Both imino-amide (Scheme 6) and imino-alkene (Scheme 7) products prepared via the bridged Ritter reaction have been reduced to the corresponding amino structures, using NaBH 4 . 12 The imine bond of the imino-amides is reduced asymmetrically to give (R)-stereocentres exclusively at C-4, with the substituent from the nitrile projecting forward from the Re face, as depicted in Scheme 6. This stereoselective outcome resulted from the imino bond being hindered by the cyclohexane ring that projects out from the Re face of the imine, only allowing for the hydride ion to approach from the Si face side.…”

“…Reductive N-methylation was carried out on (+)-6a, using the method described by Taylor et al, 12 as shown in Scheme 9, which gave (+)-10a in 45 % yield. The reaction was also attempted under the same reaction conditions with propanal, pentanal and benzaldehyde, however, none of these reactions were successful and only starting material was recovered.…”