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Synlett 2022; 33(08): 781-784
DOI: 10.1055/a-1800-2011
DOI: 10.1055/a-1800-2011
letter
Synthesis of 1,5-Disubstituted Tetrazoles from Nitrones by Using Bis(p-nitrophenyl) Phosphorazidate in the Presence of 4-(Dimethylamino)pyridine
This work was supported by JSPS KAKENHI JP22K05469, Takahashi Industrial and Economic Research Foundation (No.11-003-020), and Ichihara International Scholarship Foundation (29th Research Grant).
Abstract
A novel method has been developed for the synthesis of 1,5-disubstituted tetrazoles from nitrones by using bis(p-nitrophenyl) phosphorazidate in the presence of 4-(dimethylamino)pyridine. By this approach, various nitrones were converted into the corresponding tetrazoles. This method permits the preparation of 1,5-disubstituted tetrazoles without the need for toxic or explosive reagents.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1800-2011.
- Supporting Information
Publication History
Received: 24 February 2022
Accepted after revision: 16 March 2022
Accepted Manuscript online:
16 March 2022
Article published online:
20 April 2022
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- 11 1-Methyl-5-phenyl-1H-tetrazole (2a);1f Typical Procedure p-NO2DPPA (0.4 mmol) and DMAP (0.4 mmol) were added to a solution of nitrone (0.2 mmol) in THF (0.3 mL). The vessel was sealed, and the mixture was stirred at the reflux for 16 h. The mixture was then diluted with EtOAc (30 mL) and washed successively with 1 N aq HCl, H2O, aq NaHCO3, and brine (25 mL) then dried (Na2SO4) and concentrated in vacuo. The residue was purified by chromatography [silica gel, EtOAc–hexane (1:1 to 1:4)] to give a white solid; yield: 90%; mp 100–101 °C. 1H NMR (270 MHz, CDCl3): δ = 4.19 (s, 3 H), 7.56–7.63 (m, 3 H), 7.71–7.77 (m, 2 H).
- 12 Analytical data for the tetrazoles are provided in the Supporting Information.
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