The Synthesis of Tetrazoles in Nanometer Aqueous Micelles at Room Temperature

Abstract

A newly developed nonionic amphiphile (GPGS‐1500), a diester composed of a Guerbet alcohol (2‐octyldodecan‐1‐ol), poly(ethylene glycol) 1500 (PEG 1500), and succinic acid esters, has been prepared as an effective nanomicelle‐forming species for the synthesis of tetrazoles in water at room temperature.

The Hydrophobic Effect Applied to Organic Synthesis: Recent Synthetic Chemistry “in Water”

“…The Guerbet alcohol (2‐octyldodecan‐1‐ol) serves as the source of the lipophilic chain, together with a succinic acid linker and either PEG‐1500 (GPGS‐1500) or MPEG‐2000 (GMPGS‐2000) as the hydrophilic component (Scheme ). While the synthesis of tetrazoles by 1,3‐dipolar cycloadditions traditionally requires a significant amount of organic solvent, 5 wt % of GPGS‐1500 in water successfully enabled these reactions at room temperature . Unsubstituted or electron‐rich aryl nitriles were poor substrates, but excellent yields could be obtained with o ‐, m ‐ or p ‐cyanopyridine derivatives as well as tetrazolylpyridine N ‐oxides, thiazole or benzothiazole nitriles.…”

“…While the synthesis of tetrazoles by 1,3-dipolar cycloadditionst raditionally requiresasignificant amount of organic solvent, 5wt% of GPGS-1500 in water successfully enabled these reactions at room temperature. [70] Unsubstituted or electron-rich aryl nitrilesw ere poor substrates, but excellent yields could be obtained with o-, m-o rp-cyanopyridine derivatives as well as tetrazolylpyridine N-oxides, thiazoleo rb enzothiazolen itriles. In the presence of electron-withdrawing groups,moderate yields were obtained.…”

Synthesis of 5‐substituted 1H‐tetrazoles using a recyclable heterogeneous nanonickel ferrite catalyst

“…All synthesized tetrazoles were characterized using spectral data (FT-IR, 1 H NMR and 13 C NMR) and melting points and comparing them with authentic samples. [4,7,33,40] The FT-IR spectra of synthesized compounds showed a sharp absorption at 3421 cm À1 (N-H), a group of bands at 1455 (C-H), 1285 (N-N¼N-), 1208, 1120 and 1048 cm À1 caused by the presence of secondary amino group and tetrazole ring, and the absence of a band at 2200 cm À1 of the CN group. For example, the spectroscopic data for some products are presented in the following.…”

“…[1] They play important roles in coordination chemistry, [2] in the photographic industry [3] and in the formation of photoinducible bioorthogonal ligations for the selective covalent attachment of synthetic groups to biopolymers such as proteins. [4] Furthermore, extensive work has been accomplished in the field of medicinal chemistry. [5] They are used for their biological activities such as antibacterial, anti-inflammatory, antifungal, antiviral, antituberculous, cyclo-oxygenase inhibitory, antinociceptive, hypoglycaemic and anticancer activities.…”

One‐Pot Synthesis of Triazoles from Organic Halides and Alkynes in Nonionic Nanomicelles at Room Temperature

“…have completed a series of reactions in nonionic micelles at ambient temperature 8. More recently, we have reported the synthesis of tetrazoles in water at room temperature catalyzed by the amphiphile GPGS‐1500 9…”