A fascinating click strategy to novel 1, 2, 3-triazolium based organic-inorganic hybrids for highly accelerated preparation of tetrazolopyrimidines. (1st February 2022)

• Record Type: Journal Article
• Authors: Taib, Layla A.; Keshavarz, Mosadegh
• Is Part Of: Polyhedron. Volume 213(2022)
• Publication Date: 2022-02-01
• Subjects: BAISs Brønsted Acidic Ionic Solids -- BAILs Brønsted acidic ionic liquids -- HPA Heteropolyacid -- CuAAC Cupper catalyzed azide alkyne cycloaddition -- TBAF Tetra Butyl Ammonium Fluoride -- MSTrAzBs Mono-Substituted Triazolium-N-Butyl sulfonate -- DSTrAzBs Di-Substituted Triazolium-N-Butyl sulfonate -- DSBiTrAzBs Di-Substituted Bis Triazolium-N-Butyl sulfonate; Click reaction -- Triazole -- Sultone -- BAIS -- Tetrazolopyrimidines; Chemistry, Inorganic -- Periodicals; Chimie inorganique -- Périodiques; Organometaalverbindingen; Anorganische chemie; 546.05
• DOI: 10.1016/j.poly.2021.115630
• Languages: English
• ISSNs: 0277-5387

Abstract

Graphical abstract: Novel organic-inorganic Brønsted acidic ionic solids based on click prepared 1, 2, 3-triazolium sulfonate zwitterions are introduced as new catalysts for the efficient synthesis of tetrazolopyrimidines. Abstract: Herein, click reaction is used for the preparation of novel organic-inorganic Brønsted acidic ionic solids (BAISs) as new catalysts for the efficient synthesis of tetrazolopyrimidines. A series of mono and disubstituted-1, 2, 3-triazoles were synthesized under click reaction condition. The prepared 1, 2, 3-triazoles underwent reaction with 1, 4-butanesultone to provide novel solid 1, 2, 3-triazolium N- butyl sulfonate zwitterions. Then, the reaction of phosphotungstic acid with the obtained zwitterions led to the novel 1, 2, 3-triazolium- N -butyl sulfonic acid phosphotungstate as acidic ionic solids. The synthesized BAIS catalysts were fully characterized using FTIR, 1 H and 13 C NMR, XRD, elemental analysis (CHNS), TG and DSC techniques. The introduced novel hybrids were used as efficient catalysts for the synthesis of targeted methyl-7-aryl-4, 7-dihydrotetrazolo[1, 5- a ]pyrimidine-6-carboxylate and 6, 6-dimethyl-9-aryl-5, 6, 7, 9-tetrahydrotetrazolo[5, 1- b ]quinazolin-8(4H)-one derivatives via multicomponent reaction of aromatic aldehydes, active methylene compounds and 5-aminotetrazole. Low amount of the prepared 1, 2, 3-triazolium- N -butyl sulfonic acids phosphotungstate catalysts (5–10 mmol%) gave desired products in short times (20–45 min) with excellent yields (87–93%). Novelty of the introduced catalysts, ease of recovery and reusability up to four repeated runs with no significant decrease in the yields are highlighted superiorities of the introduced organic-inorganic hybrid catalysts.