Application of Hexamethylenetetramine in a Pictet-Spengler Type Reaction for Synthesis of Isoquinoline Derivatives

Abstract

Hexamethylenetetramine was used successfully as amino-and amidoalkylation cyclization reagent for the synthesis of 3,4-dihydroisoquinolines, tetrahydroisoquinolines and 1,4-dihydro-3(2H)-isoquinolinones.The reagent provides a simple and convenient pathway for the preparation of a range of these compounds.Hexamethylenetetramine (HMTA) as a reagent has been used as a source of -CH=N-and -CH= functions.It has been employed for introduction of formyl group usually in activated aromatic compounds (Sommelet and Duff reactions), for the synthesis of N-heterocyclic compounds 1,2 and as a Mannich