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63849284546
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Typical Procedure for the Conjugate Addition of Active Methylene 5 to β-Nitroacrylates 1 β-Nitroacrylate 2(1 mmol) and o-phenylenediamine 1 (1.25 mmol) were dissolved in EtOAc (2 mL) and mixed at r.t, with magnetic stirring, for 2 h. Then, acetone (2 mL, in order to increase the solubility of 4) and 0.8 g of SiO2 (Silica Gel 60, 0,040-0,063 mm, 230-400 mesh ASTM, Merck, were added and the mixture was stirred for 5 min. Finally, the solvent was removed under vacuum and the crude product (adsorbed on SiO2) was charged onto a chromatography column (cyclohexane-EtOAc) allowing the pure products 4. Spectroscopic Data for Representative Compounds Compound 4b (diastereomeric mixture, yellow solid. IR (KBr, v, 1362, 1546, 1686, 3049, 3414 cm-1. 1H NMR (400 MHz, acetone, δ, 0.95 (t, 3 H, J, 7.3 Hz, 1.88-2.02 (m, 1 H, 2.07-2.25 (m, 1 H, 4.39 dd, 0.27 H, J= 3.4, 6
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5 (307.30): C, 54.72; H, 5.58; N, 13.67. Found: C, 54.36; H, 5.31; N, 13.83.
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