Efficient and suitable preparation of N-sulfonyl-1,2,3,4-tetrahydroisoquinolines and ring analogues using recyclable H6P2W18O62 .24H2O/SiO2 catalyst

PASQUALE, GUSTAVO; RUIZ, DIEGO M.; AUTINO, J. C; BARONETTI, G.T; THOMAS, H.J.; ROMANELLI, G

COMPTES RENDUS CHIMIE

ELSEVIER FRANCE-EDITIONS SCIENTIFIQUES MEDICALES ELSEVIER

Lugar: Paris; Año: 2012 vol. 15 p. 758 - 763

1631-0748

Silica gel-supported H6P2W18O62·24H2O is an efficient and recyclable catalyst for the synthesis of biologically important molecules. Several substituted N-sulfonyl-1,2,3,4-tetrahydroisoquinolines and ring analogues can be prepared in very good yields and purity by direct reaction of N-aralkylsulfonamides and sym-trioxane by a Pictet-Spengler reaction in the presence of a catalytic amount of silica gel-supported H6P2W18O62·24H2O. Reactions were performed in a low volume of toluene, at 70 °C and for a short time, typically 15 to 30 min. The title heterocyclic compounds were prepared in very good yields (60%–95%) using the described procedure results in a clean and useful alternative, which has the advantages of a greener methodology with operative simplicity, use of a reusable and non-corrosive solid catalyst, soft reaction conditions, low reaction times, and good yields.