Silver-Catalyzed Direct Regioselective Phosphonation of Thiazolo[3,2-b]-1,2,4-triazoles with Dialkyl Phosphites

Abstract

An efficient and generally applicable protocol for the silver-catalyzed direct phosphonation of thiazolo[3,2-b]-1,2,4-triazoles with dialkyl phosphites has been developed. This transformation gives phosphonated products in moderate to good yields with high regioselectivity.

Key words

phosphonation - thiazolo[3,2-b]-1,2,4-triazole - dialkyl phosphites - AgOAc - regioselectivity

• References and Notes

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• 13 Synthesis Procedure and Spectroscopic Data of 3a 6-Phenylthiazolo[3,2-b]-1,2,4-triazole (1a, 101 mg, 0.5 mmol), diethyl phosphite (2a, 138 mg, 1 mmol), AgOAc (8.4 mg, 10 mol%), K₂S₂O₈ (270 mg, 2.0 equiv), and MeCN (3 mL) were sequentially added to a 25-mL Schlenk flask equipped with a high-vacuum PTFE valve-to-glass seal. Then the flask was sealed and stirred at 80 °C for 24 h. After completion of the reaction (monitored by TLC), H₂O (10 mL) was added. The aqueous solution was extracted with EtOAc (3 × 10 mL), and the combined extract was dried with anhydrous Na₂SO₄. The solvent was removed, and the crude product was separated by column chromatography (eluted with PE–EtOAc, 3:1) to give a pure sample of 3a as colorless oil; yield 115 mg (68%). ¹H NMR (400 MHz, CDCl₃): δ = 8.22 (s, 1 H), 7.89 (m, 2 H), 7.56 (m, 3 H), 4.17–4.03 (m, 4 H), 1.21 (t, J = 7.0 Hz, 6 H). ¹³C NMR (100 MHz, CDCl₃): δ = 157.8 (d, J = 8.2 Hz), 157.4, 138.4 (d, J = 17.8 Hz), 131.0, 129.8, 128.6, 126.8 (d, J = 1.8 Hz), 114.1 (d, J = 212.3 Hz), 63.6 (d, J = 5.7 Hz), 16.0 (d, J = 6.6 Hz). ³¹P NMR (162 MHz, CDCl₃): δ = 7.58. ESI-MS: m/z = 338 [M + H]⁺. Anal. Calcd: C, 49.85; H, 4.78; N, 12.46. Found: C, 49.73; H, 4.72; N, 12.31.