73083-01-9Relevant academic research and scientific papers
A variation of the Pictet-Spengler reaction via a sequential reduction-cyclization reaction of N-acylcarbamates: synthesis of 1-substituted tetrahydroisoquinoline derivatives
Kuhakarn, Chutima,Panyachariwat, Nattakan,Ruchirawat, Somsak
, p. 8182 - 8184 (2007)
A new variation of the Pictet-Spengler reaction for the synthesis of 1-substituted tetrahydroisoquinoline derivatives has been developed. The reaction employs the reduction of N-acylcarbamates by DIBAL-H followed by simultaneous cyclization mediated by BF3·OEt2. The synthetic potential of this method has been illustrated by the synthesis of the tetrahydroisoquinoline alkaloids, (±)-xylopinine, (±)-laudanosine, (±)-8-oxo-O-methylbharatamine, and (±)-isoindoloisoquinolone.
One-pot α-amidosulfone-mediated variation of the pictet-Spengler tetrahydroisoquinoline synthesis, suitable for amide-type substrates
Arroyo, Francisco J.,López-Alvarado, Pilar,Ganesan,Menéndez, J. Carlos
, p. 5720 - 5727 (2014/11/07)
The development of Pictet-Spengler reactions from amide substrates is a challenging problem. We report here that the reaction between amide-type compounds (including carbamates, amides, ureas and diketopiperazines), aldehydes and p-toluenesulfinic acid constitutes an efficient method for the preparation of tetrahydroisoquinolines or pyrazino-[2,1-b]isoquinolines. Unlike previously known methods, this one-pot Pictet-Spengler protocol avoids the need for strong Lewis or Br?nsted acid catalysts.
Synthesis and contractile activity of substituted 1,2,3,4- tetrahydroisoquinolines
Ivanov, Iliyan,Nikolova, Stoyanka,Aladjov, Dimo,Stefanova, Iliyana,Zagorchev, Plamen
, p. 7019 - 7042 (2011/11/05)
A series of different 1-monosubstituted and 1,1-disubstituted 1,2,3,4-tetrahydroisoquinolines was synthesized in high yields from different ketoamides. We have developed a convenient method for the synthesis of disubstituted derivatives by interaction of
