140381-75-5Relevant academic research and scientific papers
One-pot functionalisation of N-substituted tetrahydroisoquinolines by photooxidation and tunable organometallic trapping of iminium intermediates
Barham, Joshua P.,John, Matthew P.,Murphy, John A.
, p. 2981 - 2988 (2014)
Nucleophilic trapping of iminium salts generated via oxidative functionalisation of tertiary amines is well established with stabilised carbon nucleophiles. The few reports of organometallic additions have limited scope of substrate and organometallic nucleophile. We report a novel, one-pot methodology that functionalises N - substituted tetrahydroisoquinolines by visible lightassisted photooxidation, followed by trapping of the resultant iminium ions with organometallic nucleophiles. This affords 1,2-disubstituted tetrahydroisoquinolines in moderate to excellent yields.
Ring-opening Reactions of N-Aryl-1,2,3,4-tetrahydroisoquinoline Derivatives
Hedley, K. Andrew,Stanforth, Stephen P.
, p. 743 - 750 (2007/10/02)
The reaction of N-nitroaryl-1,2,3,4-tetrahydroisoquinolines 1a-e, 1g and 1j with N-bromosuccinimide (NBS) afforded aldehydes 3a-e, 3h and 3j respectively.N-(4-Nitrophenyl)-1-phenyl-1,2,3,4-tetrahydroisoquinoline 1n gave ketone 3n together with brominated product 3o when treated with NBS.
