Aminotetrazole Synthesis from Secondary Amides by C–C Bond Nitrogenation

Cheng Zhang; Jianzhong Liu; Zengrui Cheng; Junhua Li; Song Song; Ning Jiao

doi:10.1055/a-2006-4548

Synlett, Table of Contents

Synlett 2023; 34(12): 1534-1538
DOI: 10.1055/a-2006-4548

cluster

Special Issue Honoring Masahiro Murakami’s Contributions to Science

Aminotetrazole Synthesis from Secondary Amides by C–C Bond Nitrogenation

Authors

Cheng Zhang

^aState Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Rd. 38, Beijing 100191, P. R. of China
Jianzhong Liu

^aState Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Rd. 38, Beijing 100191, P. R. of China
Zengrui Cheng

^aState Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Rd. 38, Beijing 100191, P. R. of China
Junhua Li

^aState Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Rd. 38, Beijing 100191, P. R. of China
Song Song

^aState Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Rd. 38, Beijing 100191, P. R. of China
Ning Jiao ∗

^aState Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Rd. 38, Beijing 100191, P. R. of China

^bShanghai Key Laboratory of Green Chemistry and Chemical Processes, East China Normal University, Shanghai 200062, P. R. of China

Abstract

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Abstract

The development of novel methods for the preparation of aminotetrazoles is of long-standing interest to chemists due to the great importance of these compounds in chemistry and biology. Here, we report an efficient method for the preparation of aminotetrazoles from secondary amides by selective C–C bond cleavage. Compared with the conventional laborious and cumbersome approaches to aminotetrazoles, this chemistry provides a highly efficient nitrogenation strategy, with the installation of four nitrogen atoms into a secondary amide in one step.

Key words

aminotetrazoles - secondary amides - C–C bond cleavage - rearrangement - nitrogenation

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References

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17 Aminotetrazoles 2a–y; General ProcedureUnder air, the appropriate secondary amide 1 (0.3 mmol) was dissolved in TCE (1 mL, 0.3 M) and Tf₂O (169 mg, 0.6 mmol) was added at 0 °C. The mixture was stirred at 0 °C for 15 min, then TMSN₃ (104 mg, 0.9 mmol) was added and the mixture was warmed to 40 °C. The vial was sealed, and the mixture was stirred under air at 40 °C for 24 h then cooled to RT. The reaction was quenched with Et₃N (5 mL) at 0 °C, and the mixture was diluted with EtOAc (12 mL). The organic phase was filtered through a pad of silica gel using EtOAc to dilute the product. The filtrate was concentrated and the residue was purified by flash chromatography (silica gel). N-Methyl-1-phenyl-1H-tetrazol-5-amine (2a)Yellow solid; yield: 33.6 mg (64%). ¹H NMR (400 MHz, CDCl₃): δ = 7.53–7.47 (m, 2 H), 7.47–7.40 (m, 3 H), 4.86 (br s, 1 H), 3.06 (d, J = 4.8 Hz, 3 H). ¹³C NMR (100 MHz, CDCl₃): δ = 155.29, 133.05, 130.06, 129.62, 123.80, 30.70. HRMS (ESI): m/z [M + H]⁺ calcd for C₈H₁₀N₅: 176.0931; found: 176.0935

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