Silver-Catalyzed [3+3] Annulation of Glycine Imino Esters with Seyferth–Gilbert Reagent To Access Tetrahydro-1,2,4-triazinecarboxylate Esters

Yin-Jun Huang; Jing Nie; Chi Wai Cheung; Jun-An Ma

doi:10.1055/s-0039-1690894

Synlett, Table of Contents

Synlett 2020; 31(11): 1107-1111
DOI: 10.1055/s-0039-1690894

letter

Silver-Catalyzed [3+3] Annulation of Glycine Imino Esters with Seyferth–Gilbert Reagent To Access Tetrahydro-1,2,4-triazinecarboxylate Esters

Yin-Jun Huang

^aDepartment of Chemistry, Tianjin Key Laboratory of Molecular Optoelectronic Sciences, and Tianjin Collaborative Innovation Centre of Chemical Science and Engineering, Tianjin University, Tianjin 300072, P. R. of China

,

Jing Nie

^aDepartment of Chemistry, Tianjin Key Laboratory of Molecular Optoelectronic Sciences, and Tianjin Collaborative Innovation Centre of Chemical Science and Engineering, Tianjin University, Tianjin 300072, P. R. of China

,

Chi Wai Cheung ∗

^aDepartment of Chemistry, Tianjin Key Laboratory of Molecular Optoelectronic Sciences, and Tianjin Collaborative Innovation Centre of Chemical Science and Engineering, Tianjin University, Tianjin 300072, P. R. of China

^bJoint School of National University of Singapore and Tianjin University, International Campus of Tianjin University, Binhai New City, Fuzhou 350207, P. R. of China Email: zhiwei.zhang@tju.edu.cn Email: majun_an68@tju.edu.cn

,

Jun-An Ma ∗

^aDepartment of Chemistry, Tianjin Key Laboratory of Molecular Optoelectronic Sciences, and Tianjin Collaborative Innovation Centre of Chemical Science and Engineering, Tianjin University, Tianjin 300072, P. R. of China

^bJoint School of National University of Singapore and Tianjin University, International Campus of Tianjin University, Binhai New City, Fuzhou 350207, P. R. of China Email: zhiwei.zhang@tju.edu.cn Email: majun_an68@tju.edu.cn

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Abstract

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Abstract

A silver-catalyzed protocol for [3+3] annulation of glycine imino esters with Seyferth–Gilbert reagent was developed. A variety of phosphorylated tetrahydro-1,2,4-triazinecarboxylate esters were synthesized in moderate to good yields and with excellent diastereoselectivities. The dehydrogenation of a tetrahydro-1,2,4-triazine product to the corresponding triazine counterpart was also demonstrated.

Key words

[3+3] annulation - glycine imino esters - Seyferth–Gilbert reagent - triazines - phosphorylation

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References

References and Notes

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16 CCDC 1977600 contains the supplementary crystallographic data for compound 3b. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.
17 Methyl 5-(4-Aryl)-6-(diethoxyphosphoryl)-1,4,5,6-tetrahydro-1,2,4-triazine-3-carboxylates 3a–q; General Procedure An oven-dried 10 mL Schlenk tube equipped with a stirring bar and capped with a rubber septum was charged with the appropriate glycine imino ester 1 (1.5 equiv, 0.45 mmol), AgF (0.03 mmol, 10 mol %), and Cs₂CO₃ (1 equiv, 0.30 mmol). The tube was evacuated and backfilled with argon three times. THF (1.5 mL) was transferred into the tube under a positive argon pressure by using a syringe. A solution of Seyferth–Gilbert reagent 2 (1 equiv, 0.3 mmol) in THF (1.5 mL) was then transferred into the mixture by syringe under a positive argon pressure, and the mixture was stirred under argon at rt for 12 h. The mixture was finally concentrated in vacuo in a rotary evaporator and the residue was purified by flash chromatography [silica gel, PE–EtOAc then EtOAc–MeOH (20:1)]. Methyl 5-(4-Chlorophenyl)-6-(diethoxyphosphoryl)-1,4,5,6-tetrahydro-1,2,4-triazine-3-carboxylate (3a) Brown solid; yield: 85.6 mg (73%); mp 120–122 °C. ¹H NMR (400 MHz, CDCl₃): δ = 7.34–7.29 (m, 2 H), 7.25–7.21 (m, 2 H), 5.73 (s, 1 H), 5.56 (t, J = 2.2 Hz, 1 H), 4.78–4.83 (m, 1 H), 4.11–3.90 (m, 4 H), 3.86 (s, 3 H), 3.21–3.17 (m, 1 H), 1.24 (t, J = 7.1 Hz, 3 H), 1.12 (t, J = 7.1 Hz, 3 H). ³¹P NMR (162 MHz, CDCl₃): δ = 20.08 (p, J = 8.0 Hz). ¹³C NMR (101 MHz, CDCl₃): δ = 162.1, 138.7 (d, J = 4.5 Hz), 136.2, 134.5, 129.0, 128.8, 63.0 (d, J = 6.7 Hz), 62.7 (d, J = 7.0 Hz), 54.2, 53.1, 52.9 (d, J = 154.1 Hz), 16.5 (d, J = 5.9 Hz), 16.3 (d, J = 6.1 Hz). HRMS (ESI): m/z [M + H]⁺ calcd for C₁₅H₂₂ClN₃O₅P: 390.0980; found: 390.0981.

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