Synthesis of New bis 1- and 5-Substituted 1H-Tetrazoles via Huisgen-Type 1,3-Dipolar Cycloadditions

Abstract

The synthesis and characterization of one symmetrical bis-1-substituted-1H-tetrazole (69%) via a Huisgen-type 1,3-dipolar cycloaddition, as well as, one symmetrical aza-linked bis-5-substituted-1H-tetrazole (57%) via a classic Huisgen 1,3-dipolar cycloaddition followed by a reductive aza-coupling under greener reaction conditions are described. The main reason behind these tetrazole-based ligands is to construct novel Metal-Organic Framework (MOF) architectures to evaluate their CO2 capture properties under relative humidity conditions. It is worthy to note that both herein reported products have not been synthesized nor isolated, anywhere. Besides, the synthesis of new ligands to fabricate novel MOFs with potential application in environmental remediation has become a highly valued field of opportunity for synthetic chemists and materials engineers.

Advances in Tetrazole Synthesis – An Overview

“…For these reasons, the synthesis of tetrazole containing heterocyclic nucleus is very significant. The catalysts used for the tetrazole synthesis are nanocrystalline ZnO, [47] Yb(OTf) 3 , [48] Zn/Al hydrotalcite, [48] Zn(OTf) 3 , [49] Zn hydroxyapatite, [50] FeCl 3 ‐SiO 2 , [51] Cu 2 O, [52,53] CdCl 2 , [54] mesoporous ZnS nanospheres, [55] BaWO4,γ‐Fe 2 O 3 , [56] ZnS nanoparticles, [57] Copper (II) supported on Fe 3 O 4 @SiO 2 nanoparticles, [58] CoYzeolite [59] and Pd(OAc) 2 ‐ZnBr 2 [60] or even with precursors of MOFs [61] …”

“…The catalysts used for the tetrazole synthesis are nanocrystalline ZnO, [47] Yb(OTf) 3 , [48] Zn/Al hydrotalcite, [48] Zn(OTf) 3 , [49] Zn hydroxyapatite, [50] FeCl 3 -SiO 2 , [51] Cu 2 O, [52,53] CdCl 2 , [54] mesoporous ZnS nanospheres, [55] BaWO4,γ-Fe 2 O 3 , [56] ZnS nanoparticles, [57] Copper (II) supported on Fe 3 O 4 @SiO 2 nanoparticles, [58] CoYzeolite [59] and Pd(OAc) 2 -ZnBr 2 [60] or even with precursors of MOFs. [61] There have been several reviews and book chapters published on A to Z about tetrazoles which discuss the advancements in the chemistry and synthesis processes of tetrazoles. [62,35,[63][64][65][66][67][68][69] These reviews majorly cover the derivatization of tetrazoles, different synthesis methods, and their applications.…”