Synthesis 2020; 52(17): 2469-2482
DOI: 10.1055/s-0040-1707160
short review
© Georg Thieme Verlag Stuttgart · New York

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

Dong Liang
,
Wen-Jing Xiao
,
Our work in this area was sponsored by the National Natural Science Foundation of China (No. 91856119, 21820102003, 91956201, and 21772053), and Plan 111 (No. B17019) (Program of Introducing Talents of Discipline to Universities of China, 111 Program, B17019).
Further Information

Publication History

Received: 04 May 2020

Accepted after revision: 25 May 2020

Publication Date:
06 July 2020 (online)


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

 
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