Synthesis of 5-Substituted 1H-Tetrazoles from Aldoximes Using Diphenyl Phosphorazidate

Kotaro Ishihara; Mayumi Kawashima; Takayuki Shioiri; Masato Matsugi

doi:10.1055/s-0035-1561668

Synlett, Table of Contents

Synlett 2016; 27(15): 2225-2228
DOI: 10.1055/s-0035-1561668

letter

Synthesis of 5-Substituted 1H-Tetrazoles from Aldoximes Using Diphenyl Phosphorazidate

Kotaro Ishihara

Department of Applied Biological Chemistry, Faculty of Agriculture, Meijo University, 1-501 Shiogamaguchi, Tempaku-ku, Nagoya 468-8502, Japan Email: matsugi@meijo-u.ac.jp

,

Mayumi Kawashima

Department of Applied Biological Chemistry, Faculty of Agriculture, Meijo University, 1-501 Shiogamaguchi, Tempaku-ku, Nagoya 468-8502, Japan Email: matsugi@meijo-u.ac.jp

,

Takayuki Shioiri

Department of Applied Biological Chemistry, Faculty of Agriculture, Meijo University, 1-501 Shiogamaguchi, Tempaku-ku, Nagoya 468-8502, Japan Email: matsugi@meijo-u.ac.jp

,

Masato Matsugi*

Department of Applied Biological Chemistry, Faculty of Agriculture, Meijo University, 1-501 Shiogamaguchi, Tempaku-ku, Nagoya 468-8502, Japan Email: matsugi@meijo-u.ac.jp

› Author Affiliations

Abstract

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Abstract

A novel method for the synthesis of 5-substituted 1H-tetrazoles using diphenyl phosphorazidate (DPPA) has been developed. Aromatic and aliphatic aldoximes underwent cycloaddition to afford the corresponding 5-substituted 1H-tetrazoles with ease and efficiency.

Key words

diphenyl phosphorazidate - aldoximes - azides - cycloaddition - tetrazoles

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References

References and Notes

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28 General Procedure DPPA (0.30 mmol) and DBU (0.60 mmol) were added to a solution of aldoxime (0.20 mmol) in toluene (1.0 mL). After stirring for 16 h at reflux, the mixture was cooled to room temperature and sat. NaHCO₃ aq (2.0 mL) was added. After stirring for 5 min, the mixture was diluted with water (20 mL). The aqueous layer was then washed with EtOAc (25 mL) and acidified with 1.0 N HCl aq to pH 2. The aqueous layer was extracted with EtOAc (2 × 30 mL), and the combined organic extracts were washed with brine (30 mL) and dried over Na₂SO₄. The concentration of the solvent in vacuo followed by the purification of the residue through a short silica gel column (EtOAc–n-hexane = 1:1 to 3:1) gave the desired tetrazole. Analytical Data for 5-Phenyl-1H-tetrazole (Table 2, Entry 1) White solid; mp 214 °C. ¹H NMR (270 MHz, DMSO-d ₆): δ = 7.60–7.66 (m, 3 H), 8.03–8.07 (m, 2 H).
29 Analytical data for tetrazoles are provided in the Supporting Information.

Supplementary Material

Supporting Information