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

Key words

hexahydro-1,3,5-triazines - 1,3,5-triazinanes - formald­imines - aminomethylations - cycloadditions - nitrogen-containing compounds

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