New 1,2,4-triazine-containing podands: synthesis and properties

Abstract

A method of one step C-C coupling of 1,5 bis(2,6 dimethylphenoxy) 3 oxapentane (1a) and 1,8 bis(2,6 dimethylphenoxy) 3,6 dioxaoctane (1b) with 3 methylthio (2) and 3 amino 1,2,4 triazine (3) and 3 aryl 1,2,4 triazin 5 one (6-8) has been described. The reaction of compounds 1a,b with compounds 2 and 3 in the presence of trifluoroacetic acid results in the addition of the dimethylphenoxy group to the unsubstituted C(5) carbon atom of the triazine ring. The reactions of triazinones 6-8 with compounds 1a,b in a mixture of trifluoroacetic acid and organic anhydrides are accompanied by the acylation of the nitrogen atom adjacent to the reaction center and affords bis[(3 R 1 acyl 5 oxo 1,4,5,6 tetrahydro 1,2,4 triazin 6 yl) 2,6 dimethylphenoxy] 3 oxapentane or 3,6 dioxaoctane. The obtained adducts can smoothly be oxidized under mild conditions to form more stable products of nucleophilic hydrogen substi tution in the triazine ring. The extraction and transport of Ca 2+ and Mg 2+ cations through an organic membrane by the compounds synthesized are discussed.

Calix[n]pyrroles as Anion and Ion-Pair Complexants

“…Sarker and co-workers have refined Sessler's method of preparation [38] with a route that circumvents the need for purification of this material by column chromatography [39,40] Chupakhin and co-workers have reported the first example of direct heterylation of a calix [4]pyrrole. Reaction of protonated 3-methylthio-(11) and 3-amino-1,2,4-triazines (12) with compound 1 in CF 3 COOH gave adducts 13 and 14 (Scheme 3) [41].…”

One-Step Heterylation at the Upper Rim of Calix[4]arene with 1,2,4-Triazin-5(2H)-ones

“…We have recently elaborated a convenient method for functionalization of 1,2,4-triazin-5(2 H )-ones with fragments of π-excessive carbo- and heterocycles. It has been shown that, being activated with acylating agents, 2-acyl-1,2,4-triazin-5(2 H )-ones are capable of reacting with phenols to give a new C−C bond between unsubstituted carbon atoms of two aromatic rings . This work exploits the same methodology to perform heterylation of calixarene rings with 1,2,4-triazin-5(2 H )-ones.…”