A suitable preparation of N-sulfonyl-1,2,3,4-tetrahydroisoquinolines and their ring homologs with a reusable Preyssler heteropolyacid as catalyst.
The preparation of N-sulfonyl-1,2,3,4-tetrahydroisoquinolines, N-sulfonyl-2,3,4,5-tetrahydro-1H-2-benzazepines and N-sulfonyl-1,2,3,4,5,6-hexahydrobenzazocine was catalyzed by a Preyssler heteropolyacid, H(14)[NaP(5)W(30)O(110)], (PA), supported on silica (PASiO(2)40) with excellent yields by means of the Pictet-Spengler reaction of N-aralkylsulfonamides with s-trioxane. The reactions proceed with 0.5 mol% of silica-supported catalyst in toluene at 70°C. The catalyst can be recycled without appreciable loss of the catalytic activity.
Romanelli
Gustavo P
GP
Centro de Investigación y Desarrollo en Ciencias Aplicadas Dr. Jorge J. Ronco (CINDECA-CCT-CONICET), Departamento de Química, Universidad Nacional de La Plata, Calle 47 No. 257, B1900AJK, La Plata, Argentina. gpr@quimica.unlp.edu.ar
Ruiz
Diego M
DM
Autino
Juan C
JC
Giaccio
Héctor E
HE
D000143:Acids / Q000737:chemistry / Q000494:pharmacology*; D002384:Catalysis / Q000187:drug effects; D002625:Chemistry, Organic / Q000379:methods; D002626:Chemistry, Pharmaceutical / Q000379:methods; D017743:Equipment Reuse; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D008954:Models, Biological; D013457:Sulfur Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D044005:Tetrahydroisoquinolines / Q000138:chemical synthesis* / Q000737:chemistry*
D000143:Acids; D006571:Heterocyclic Compounds; D013457:Sulfur Compounds; D044005:Tetrahydroisoquinolines; C014843:1,2,3,4-tetrahydroisoquinoline