Synthesis of New Metal-Free 1,4,8,11-Tetraaza[14]annulene Derivatives Using 2-Heteroaryl-substituted Trimethinium Salts

Abstract

The reaction of 2‐heteroaryl‐substituted trimethinium salts (A, B, and C) with aromatic 1,2‐diamines (a, b, c, d, and e) in acetonitrile/acetic acid leads to 6,13‐disubstituted 1,4,8,11‐tetraaza[14]annulene derivatives (1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14). The UV–vis spectral behavior of these compounds was examined in acetonitrile. Elemental analysis, IR, 1H‐NMR, 13C‐NMR, and mass spectra confirm the molecular structure of the newly synthesized compounds.

Synthesis and characterization of new derivatives of bis(1,4‐diazepinium) salts and bis(γ‐substituted pentamethine cyanine(dyes using vinamidinium salt

“…Today, vinamidinium salts are among the most useful precursors for the synthesis of some organic compounds under mild conditions . These salts are generated from an acetic acid derivative, utilizing Vilsmeier‐Haack‐Arnold formylation as described in our previous works . 1,4‐Diazepines derivatives are commonly used as painkillers, sedatives, antidepressants and hypnotics .…”

A facile and efficient route to one-pot synthesis of new cyclophanes using vinamidinium salts

“…As shown in Scheme 3, the procedure is done in two-step: (i) synthesis of the 2-substituted vinamidinium salts (2a-g) by the Vilsmeier-Arnold formylation of the substituted acetic acids (1a-g) as explained in authors previous work; [67][68][69][70][71][72][73][74][75][76] and (ii) synthesis of cyclophane derivatives (5a-f, 6a-g) by the reaction of 2-substituted vinamidinium salts (2a-g) with 1,4- 4) in reuxing acetonitrile in the presence of acetic acid for 15 h to manage the cyclophane derivatives (5a-f, 6ag). To provide the best reaction conditions in second step, the reaction of vinamidinium salt 2f with 1,4-phenylenedimethanamine (3) was chosen as model reaction and the impacts of solvents and catalysts were investigated.…”

“…They can easily undergo condensation reaction with bifunctional nucleophiles to form heterocycles. During past years, our group has been investigated the utilization of vinamidinium salts for the synthesis of heterocyclic compounds [67][68][69][70][71][72][73][74][75][76] (Scheme 2).…”

Synthesis of new metal‐free 1,2,4,5,9,10,12,13‐octaaza[16]annulene derivatives using the reaction of vinamidinium salts with thiocarbohydrazide

“…Vinamidinium salts [1A‐10A] were prepared according to literature procedures. [ 33–36 ] Thiocarbohydrazide was synthesized according to literature procedures. [ 37,38 ] 1H and 13C‐NMR spectra were recorded with a Bruker Avance DRX‐300.…”