Recent Advances of 1,3,5-Triazinanes in Aminomethylation and Cycloaddition Reactions

Abstract

1,3,5-Trisubstituted 1,3,5-triazinanes (hexahydro-1,3,5-triazines), as stable and readily available surrogates for formaldimines, have found extensive applications for the construction of various nitrogen-containing compounds. The formaldimines, formed in situ from this reagent class, can participate in various aminomethylation and cycloaddition­ reactions. This short review presents recent advances in this field with emphasis on the conceptual ideas behind the developed methodologies and the reaction mechanisms. 1 Introduction 2 Aminomethylations with 1,3,5-Triazinanes 3 Cycloadditions with 1,3,5-Triazinanes 3.1 Use of 1,3,5-Triazinanes as Two-Atom Synthons 3.2 Use of 1,3,5-Triazinanes as Three-Atom Synthons 3.3 Use of 1,3,5-Triazinanes as Four-Atom Synthons 3.4 Use of 1,3,5-Triazinanes as Six-Atom Synthons 4 Conclusions.