Synthesis and Applications of 1,3,5-Triazinanes

Abstract

The substances belonging to the class heterocyclic 1,3,5-triazinanes are extremely important because they stand out for the variety of biological activities, technological applications, such as insecticides, explosives and reagents for various organic reactions. In organic synthesis they are considered as being substances with simple preparation and low cost, which present an option for obtaining various other heterocyclic compounds, such as: imidazole, imine, aziridine, and diazirinamacrocycles.Keywords: Azoheterocycles; Synthesis; 1,3,5-Triazinanes; Formaldehyde. ResumoOs heterociclos da classe 1,3,5-triazinana são importantes por se destacarem pela grande variedade de atividades biológicas e aplicações tecnológicas, por exemplo, inseticidas, explosivos, e como reagentes para diversas reações orgânicas. Em síntese orgânica esse composto heterocíciclo se destaca por ser uma substância de simples preparação, custo baixo e que se apresenta como opção para obtenção de vários outros compostos heterociclos, como imidazol, imina, aziridina, diazirina e sistemas macrociclos.

Raise the anchor! Synthesis, X-ray and NMR characterization of 1,3,5-triazinanes with an axial tert-butyl group

“…This discovery enlarges a very small family of unanchored tert-butyl groupbearers in the solid phase and also highlights an important conformational characteristic of 1,3,5-triazinane framework useful for consideration during crystals design. 20 On the contrary, it was detected that the conformers with an equatorial arrangement of all substituents predominate in solutions at temperatures below −100 °С. The role of intramolecular hydrogen bonding in the stabilization of the tertbutyl group axial position in a 1,3,5-triazinane ring is highlighted.…”

Structural and Dynamic Behaviour of Heterocycles Derived from Ethylenediamines with Formaldehyde: 1,3,5-Triazinanes and Bis(imidazolidinyl)methanes

“…13 15 N NMR (41 MHz, CDCl 3 ) δ: −327.6 (N1), −327.9 (N3). LRMS (EI, 20 eV), m/z (%): 335 (3), 292 (2), 251 (2), 220 (13), 205 (42), 175 (91), 161 (54), 146 (6), 132 (16), 119 (10), 99 (16), 91 (100), 83 (37), 72 (14), 57 (18), 42 (37) ), 4.17 (s, 4H, H2), 3.47 (s, 2H, H6), 3.42 (t, 4H, J = 6.6 Hz, H4), 3.13 (t, 4H, J = 6.6 Hz, H5). 13 C NMR (101 MHz, CDCl 3 ) δ: 146.7 (C i ), 129.4 (C m ), 116.5 (C p ), 111.8 (C o ), 74.5 (C6), 69.1 (C2), 51.0 (C5), 45.8 (C4).…”

“…On the other hand, 1,3,5-triazinanes are exceptionally important because they have three nitrogen atoms with different degrees of hybridization and are good hydrogen-bond acceptors, which is why they are widely used by the pharmaceutical and biotechnological industries [10]. In the literature, 2,4,6-trichloro-1,3,5-triazine, also named as cyanuric chloride, and 1,3,5-trichloro-1,3,5-triazine-2,4,6(1H,3H,5H)-trione, also named as trichloroisocyanuric acid, symclosene or chloreal, are known [11,12].…”

Chemodivergent (4 + 3) cycloadditions of 2-indolylmethanols with 1,3,5-triazinanes: access to polycyclic indoles

“…Herein, we describe the divergent (4 + 3) cycloadditions of 2-indolylmethanols 1 with 1,3,5-triazinanes 2 (Scheme 1C). [54][55][56] The gem-diaryl group has a significant impact on regioselectivity. Primary 2-indolylmethanols display N1-nucleophilicity, while tertiary diaryl 2-indolylmethanols exhibit C3-nucleophilicity.…”