‘Michael-Michael-Wittig’ Reactions of (2,4-Dioxobutylidene)phosphoranes with 3-Formylchromones

Abstract

4-(2′-Hydroxybenzoyl)salicylic esters and amides were prepared by domino ‘Michael-retro-Michael-Wittig’ reactions of (2,4-dioxobutylidene)triphenylphosphoranes with 3-formylchromones.

Michael-Michael-Wittig-reaction - 4-(2′-hydroxybenzoyl)salicylic esters - 4-(2′-hydroxybenzoyl)salicylic amides - (2,4-dioxobutylidene)triphenylphosphoranes

References

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9

Representative Experimental Procedure: A THF suspension (5 mL) of NaH (78 mg, 3.25 mmol) and 3b (556 mg, 1.43 mmol) was stirred under nitrogen atmosphere at 0 °C for 30 min. A THF solution (10 mL) of 2a (190 mg, 1.1 mmol) was added and the solution was stirred for 60 min at 0 °C. The reaction mixture was refluxed for 24 h, cooled and subsequently stirred for 12 h at 20 °C. To the mixture was added diethyl ether (30 mL), an aqueous solution of HCl (5 mL, 1 M) and a saturated solution of NaCl. The aqueous layer was separated and extracted with CH₂Cl₂ (3 × 10 mL). The combined organic layers were dried (MgSO₄), filtered and the solvent of the filtrate was removed in vacuo. The residue was purified by column chromatography (silica gel, diethyl ether/petroleum ether = 1:20) to give 4b (52%) as a yellow solid. Spectroscopic data of 4b: ¹H NMR (CDCl₃, 250 MHz): δ = 1.42 (t, ³ J = 7 Hz, 3 H, CH₃), 4.45 (q, ³ J = 7 Hz, 2 H, OCH ₂CH₃), 6.91 (dd, ³ J ₁ = 7 Hz, ³ J ₂ = 8 Hz, 1 H, Ar), 7.08 (d, ³ J = 8 Hz, 1 H, Ar), 7.10 (d, ³ J = 8 Hz, 1 H, Ar), 7.53 (dd, ³ J ₁ = 7 Hz, ³ J ₂ = 8 Hz, 1 H, Ar), 7.59 (d, ³ J = 8 Hz, 1 H, Ar), 7.84 (d, ³ J = 8 Hz, 1 H, Ar), 8.30 (s, 1 H, Ar), 11.34 (s, 1 H, OH), 11.87 (s, 1 H, OH). ¹³C NMR (CDCl₃, 50 MHz): δ = 14.15 (CH₃), 62.07 (CH₂), 112.47, 119.03, 129.00 (C, Ar, ortho and para to OH), 117.74, 118.51, 118.70 (CH, Ar, ortho and para to OH), 132.36, 132.95, 136.18, 136.59 (CH, Ar, meta to OH), 163.00, 164.70, 169.61 (C, C-OH, CO₂Et), 199.12 (C, CO). IR (KBr): 3178 (w), 3059 (w), 2987 (w), 2933 (w), 1683 (s), 1629 (s), 1589 (s), 1467 (m), 1444 (m), 1397 (m), 1343 (s), 1293 (s), 1262 (s), 1242 (s), 1176 (m), 1084 (m) cm^-1. MS (70 eV): m/z (%) = 286 (100) [M⁺], 121(94). Anal. Calcd for C₁₆H₁₄O₅: C, 67.31; H, 4.93. Found: C, 66.88; H, 5.18. All compounds gave satisfactory spectroscopic and analytical and/or high resolution mass data.