Synthesis of Macrocyclic Amides and Their Intermediate 2 : 1 and 3 : 2 Reaction Compounds from Diethyl Oxalate and Ethereal Oxygen-Containing Diamines

Abstract

The reaction of diethyl oxalate with ethereal oxygen-containing diamines under high-dilution conditions gave 2 : 2 reaction products, 22-, 28-, and 34-membered macrocyclic amides in good yields. From the 2 : 1-mixed reaction between diethyl oxalate and the diamines, acyclic 2 : 1 and 3 : 2 reaction products were isolated at a ratio of ca. 9 : 1. The intermediate 2 : 1 and 3 : 2 reaction products led to the 2 : 2 reaction products mentioned above and the 3 : 3 reaction products, 33-, 42-, and 51-membered macrocyclic amides, respectively, upon reaction with additional corresponding diamines. Also, other macrocyclic amides were synthesized by combining the 2 : 1 reaction products and diamines.

A novel PVC-membrane optical sensor for highly sensitive and selective determination of UO22+ ion based on a recently synthesized benzo-substituted macrocyclic diamide and dibenzoylmethane

“…The in-built configuration rigidity induced by Nsubstituted amides present in the periphery of benzomacrocycles invokes preorganization leading to ionophoric selectivity [33][34][35]. Thus, we have recently reported the successful use of macrocyclic diamides as ionophores in the preparation of PVC-based selective electrodes for Hg 2+ [36], Sr 2+ [37], Ca 2+ [38], Cs + [39], Co 2+ [40], Ag + [41], Be 2+ [42], Cu 2+ [43], and UO 2 2+ [14,19].…”

A New PVC-Membrane Electrode Based on a Thia-Substituted Macrocyclic Diamide for Selective Potentiometric Determination of Silver Ion

“…[14][15][16] The in-built configuration rigidity induced by N-substituted amides in the periphery of benzomacrocycles invokes a preorganization leading to ionophoric selectivity. [17][18][19][20][21] A number of macrocyclic diamides, prepared from salicylaldehyde derivatives and some appropriate diamine compounds, have been shown to possess wide applications in selective metal ion extraction. [22][23][24][25] Moreover, the use of some benzo-substituted macrocycles as ion carrier in preparation of PVCbased Li + and Pb 2+ ion-selective electrodes has already been reported in the literature.…”

Cesium-selective membrane electrode based on a recently synthesized 16-membered macrocyclic diamide

“…Several macrocyclic diamides prepared from salicylaldehyde derivatives and the appropriate diamino compounds [25,26,27,28] have been shown to have wide application in selective metal-ion extraction [29,30,31]. The successful use of benzo-substituted macrocyclic diamides as ion carriers in the construction of PVC-based ion-selective electrodes for Pb 2+ [32], Zn 2+ [33], Cu 2+ [34], and Sr 2+ ions [35] has also been reported.…”