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

Abstract

<jats:p>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.</jats:p><jats:p>1 Introduction</jats:p><jats:p>2 Aminomethylations with 1,3,5-Triazinanes</jats:p><jats:p>3 Cycloadditions with 1,3,5-Triazinanes</jats:p><jats:p>3.1 Use of 1,3,5-Triazinanes as Two-Atom Synthons</jats:p><jats:p>3.2 Use of 1,3,5-Triazinanes as Three-Atom Synthons</jats:p><jats:p>3.3 Use of 1,3,5-Triazinanes as Four-Atom Synthons</jats:p><jats:p>3.4 Use of 1,3,5-Triazinanes as Six-Atom Synthons</jats:p><jats:p>4 Conclusions</jats:p>

Synthesis and Cytotoxic Activity of 5-Benzoylhexahydropyrimidine Derivatives

“…Compounds containing a hexahydropyrimidine frag ment exhibit high biological activity, in particular those possessing antitumor [1], cytotoxic [2][3][4], antibacterial [5,6], antimalarial [7], antiviral [8], and nootropic [9] properties have been reported. Chemical modification of a pyrimidine ring via variation of initial components of the classical Mannich reaction [10][11][12] could change pharmacological properties and give rise to new potentially biologically active pyrimidine derivatives. We previously reported cytotoxic activity of hexahydropyrimidine derivatives containing an amino acid moiety [3].…”

Synthesis of Diversely Substituted Imidazolidines via [3+2] Cycloaddition of 1,3,5‐Triazinanes with Donor‐Acceptor Aziridines and Their Anti‐Tumor Activity

“…1,3,5-Triazinanes, as stable and readily available surrogates of formaldimines, were utilized in various nitrogen-containing heterocycle construction with various nucleophiles. [15] Most of the reactions of 1,3,5triazinanes reported so far are involved in aminomethylations [16] and cycloaddition reactions. [17] Seminal work catalyzed by Lewis acid was performed by Werz and co-workers, who reported the cycloadditions of 1,3,5-triazinanes and donor-acceptor cyclopropanes/ cyclobutanes (Scheme 2a).…”

“…1,3,5‐Triazinanes, as stable and readily available surrogates of formaldimines, were utilized in various nitrogen‐containing heterocycle construction with various nucleophiles [15] . Most of the reactions of 1,3,5‐triazinanes reported so far are involved in aminomethylations [16] and cycloaddition reactions [17] .…”

Synthesis of α‐Amino Tertiary Alkylperoxides by Lewis Acid‐Catalyzed Peroxidation of 1,3,5‐Triazines

“…[a] L. 1,3,5-Triazines, as stable and readily available surrogates of formaldimines, become great substrates for the construction of nitrogen-containing scaffolds. [12] 1,3,5-Triazines can serve as two-, [13] three-, [14] four- [15] and six-atom [16] synthons to take part in various reactions for the synthesis of nitrogen-containing compounds. Use of 1,3,5-triazines as three-atom synthons, however, has not been much developed yet.…”