An experimental and mechanism study on the regioselective click reaction toward the synthesis of thiazolidinone-triazole

Abstract

An efficient procedure for the synthesis of novel thiazolidinone triazoles through 32 cycloaddition reactions in the presence of copper(I) species was described, and the molecular mechanism of this 32CA was investigated computationally. Different possible pathways for CA process have been studied to achieve this goal, including onestep pathways for both regioisomers 1,4-and 1,5-triazoles (uncatalyzed, mono-copper, di-copper) and also monoand di-copper stepwise pathways for 1,4-disubstituted triazole. It was exhibited that the most convenient route in terms of energy barriers includes two copper ions. Based on the calculation, the reaction follows a di-copper stepwise mechanism involving the formation of a six-membered ring and then undergoes a ring contraction to a five-membered ring. The regiochemistry of the reaction was investigated based on local and global reactivity indices of reactants, the transition state stabilities calculation. The electron reorganization along the uncatalyzed one-step mechanism has been investigated by the ELF topological analysis of the bonding changes along with the CA reaction.

Synthesis and In Vitro Anticancer Activities of New 1,4‐Disubstituted‐1,2,3‐triazoles Derivatives through Click Approach

“…[28,29] However, the major problem associated with this methodology is low regioselectivity, and the reaction leads to the mixture of 1, 4-and 1,5regioisomers. [30] K.B Sharpless [31] and M. Meldal [32] groups independently re-investigated the Huisgen's 1,3-dipolar cycloaddition and improved the regioselectivity of reaction by Cu(I)catalyzed ligation of organic azides and terminal alkynes. (CuAAC reaction) offers great promise in this regard.…”

Synthesis of Ag(I)@Fum−Pr−Pyr−Benzimidazole and Its Optical and Catalytic Activities in Click Reactions

“…[28,[32][33][34] Nowadays, incred-ible efforts have been made to develop catalytic processes to achieve greener synthetic methods by reducing the chemical waste, the number of synthetic steps, and the use of an ecofriendly solvent, which results in the best yield of the product. [35][36][37][38] Silver has been extensively employed as an agent and catalyst in organic synthesis reactions. Silver nanocomposites exhibited good catalytic activity toward cycloaddition, coupling, sigmatropic, and click reactions.…”

“…Recently, an Ag‐catalyzed AAC reaction has been reported for triazole synthesis as an alternative catalyst for click reaction [28,32–34] . Nowadays, incredible efforts have been made to develop catalytic processes to achieve greener synthetic methods by reducing the chemical waste, the number of synthetic steps, and the use of an eco‐friendly solvent, which results in the best yield of the product [35–38] . Silver has been extensively employed as an agent and catalyst in organic synthesis reactions.…”