Synthesis of New Dibenzo-tetraaza and Dibenzo-dioxadiaza[14]annulene Derivatives Using 3-Bromo-substituted Vinamidinium Salt

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, functionalization and coordination chemistry of dibenzotetraaza[14]annulenes

“…The treatment of 1 with hydrochloric acid followed by basification with triethylamine produces the free ligand 2a (Scheme 1a) [29]. However, a mixture of regioisomers will be generated when a non-symmetric reactant is employed [33][34][35]. A versatile synthetic approach to afford the macrocycle core was reported by Honeybourne et al in 1978 [36].…”

“…However, the metal coordination chemistry of 2b is not widely explored owing to the insolubility of the ligand. Another example of a non-template reaction is the condensation reaction between substituted vinamidinium salts and o-phenylenediamine to generate 2c (Scheme 1c) [35,37,38].…”

Preparation and Application of Vinamidinium Salts in Organic Synthesis

“…2.4.6.6 四氮杂轮烯 四氮杂轮烯化合物为卟啉和酞菁的模型化合物, 但 它又具有一些独特的化学活性, Mehranpour [43] 以 β-溴代 vinamidinium 盐 87 为关键合成子与邻苯二胺衍生物反 应合成得到了一系列四氮杂 [14]轮烯化合物 88 [42] (Eq. …”