One-Pot Synthesis of 1H-Indazole-4,7-diols via Iodine(III)-Mediated [3+2] Cyclization in Water

Abstract

An efficient route in one-pot to a new class of 1H-indazole-4,7-diols derivatives has been developed through [3+2] cycloadditive approach in water. The cycloaddition reaction was carried out via condensation of phenol and diazomethyl benzene intermediates by taking advantage of iodobenzene diacetate as an oxidant. Eighteen indazole derivatives were successfully prepared by the established method.

Key words

synthesis - 1H-indazole-4,7-diols derivatives - one pot - water

• References and Notes

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• 22 Procedure of Preparing Compound 3ab DIB (644 mg, 2.0 mmol) was added to a solution of compound 1a (112 mg, 1.0 mmol) in TFA (12 mL) and H₂O (1%, v/v). After the mixture was stirred for 2 h at r.t., compound 2b (198 mg, 1.5 mmol) was added. The resulting solution was stirred for another 8 h at 70 °C. After the addition of Na₂S₂O₃ (2.0 mmol) in H₂O (8 mL), the mixture was poured into brine (30 mL) and extracted with CH₂Cl₂ (3 × 50 mL). The combined organic layer was washed with brine (2 × 50 mL) and dried over Na₂SO₄. After evaporation of the solvent under reduced pressure, the residue was purified by silica gel (MeOH–CH₂Cl₂, 1:100) to obtain the product 3ab (238 mg, 89% yield). ¹H NMR (500 MHz, acetone-d ₆): δ = 8.49 (s, 1 H, OH), 7.80 (d, J = 8.2 Hz, 2 H, ArH), 7.29 (d, J = 8.0 Hz, 2 H, ArH), 2.42 (s, 3 H, ArCH₃), 2.36 (s, 6 H, ArCH₃). ¹³C NMR (126 MHz, acetone-d ₆): δ = 170.94, 151.29, 145.24, 140.56, 130.94, 130.42, 130.32, 130.14, 129.32, 125.57, 21.84, 21.46. HRMS (ESI-TOF): m/z calcd for C₁₆H₁₇N₂O₂ [M + H]⁺: 269.1285; found: 269.1284.