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Synthesis of 1-tetrazolyl-1,2,3,4-tetrahydroisoquinoline bound-type bis-heterocycles via oxidative Ugi-azide reaction
1 , 2 , * 1
1  Universidad de Guanajuato
2  Universidad Autónoma Metropolitana - Iztapalapa


A series of five novel 1-tetrazolyl-1,2,3,4-tetrahydroisoquinolines were synthesized in moderate yields (29-60%) by a two-step process. The first one involved a NH-CH2 bond oxidation of the 1,2,3,4-tetrahydroisoquinoline to give the corresponding imine using IBX as oxidant. The second step was an oxidative Ugi-azide reaction using 3,4-dihydroisoquinoline, TMSN3 and the corresponding isocyanides as starting reagents. Final bis-heterocycles may find application in medicinal chemistry because tetrazole and tetrahydroisoquinoline are present in a variety of bioactive products and drugs.

Keywords: Oxidative Ugi-azide, Tetrazoles, Isoquinolines, bis-heterocycles