β-Lactam-Synthon-Interceded Metal/Acid-Free Diastereoselective Access to Highly Functionalized Oxazol-5-ones and Dihydroimidazoles

Abstract

Facile diastereoselective access to functionalized oxazol-5-ones and dihydroimidazoles was accomplished through base-promoted intramolecular amidolysis and methoxide-assisted tandem intramolecular amidolysis/ring opening/intramolecular cyclization, respectively, of C-3-functionalized azetidin-2-ones.

Key words

azetidinones - oxazolones - dihydroimidazoles - amidolysis - diastereoselectivity - tandem reaction

• References

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• 29 Oxazol-5-ones (3a–f); General Procedure A solution of the appropriate azetidinone 2 (1.0 mmol) in anhyd DMF (5 mL) was added dropwise to a stirred suspension of t-BuOK (1.2 mmol) in anhyd DMF (5 mL), and the mixture was stirred at r.t. for 30 min. When the reaction was complete (TLC), the mixture was concentrated under reduced pressure and extracted with EtOAc (3 × 20 mL). The combined organic layers were dried (Na₂SO₄), filtered, and concentrated under vacuum to afford a crude product that was purified by column chromatography [silica gel, EtOAc–hexane (40:60)].
• 30 2-Methyl-4-{(2E)-1-[(4-tolyl)amino]-3-phenylprop-2-en-1-yl}-1,3-oxazol-5(4H)-one (3b) Off-white solid; yield: 92 mg (80%); mp 160–162 °C. ¹H NMR (400 MHz, CDCl₃): δ = 2.03 (s, 3 H, CH₃), 2.26 (s, 3 H, CH₃), 4.53 (dd, J _1,2 = 1.76, J _1,3 = 7.88 Hz, 1 H, H-2), 4.78 (dd, J _1,2 = 2.12, J _1,3 = 7.32 Hz, 1 H, H-1), 6.28 (dd, J _1,2 = 7.92, J _1,3 = 15.96 Hz, 1 H, H-3), 6.73 (d, J = 15.9 Hz, 1 H, H-4), 7.04 (d, J = 8.2 Hz, 2 H, Ar-H), 7.24–7.36 (m, 7 H, Ar-H). ¹³C NMR (100 MHz, CDCl₃): δ = 21.0, 22.9, 62.8, 63.3, 117.4, 124.9, 126.8, 128.4, 128.7, 129.7, 134.2, 134.7, 135.0, 135.6, 164.0, 170.7. HRMS: m/z [M⁺] calcd for C₂₀H₂₀N₂O₂: 320.1525; found. 320.1530. 4-{(2E)-1-[(4-Chlorophenyl)amino]-3-phenylprop-2-en-1-yl}-2-methyl-1,3-oxazol-5(4H)-one (3c) Off-white solid; yield: 90.3 mg (79%); mp 164–165 °C. ¹H NMR (400 MHz, CDCl₃): δ = 2.03 (s, 3 H, CH₃), 4.62 (dd, J _1,2 = 2.00, J _1,3 = 8.08 Hz, 1 H, H-2), 4.73 (dd, J _1,2 = 2.3, J _1,3 = 7.32 Hz, 1 H, H-1), 6.28 (dd, J _1,2 = 8.04, J _1,3 = 15.92 Hz, 1 H, H-3), 6.76 (d, J = 15.92 Hz, 1 H, H-4), 7.21 (d, J = 8.8 Hz, 2 H, Ar-H), 7.26–7.37 (m, 7 H, Ar-H). ¹³C NMR (100 MHz, CDCl₃): δ = 22.9, 62.7, 63.8, 118.6, 124.4, 126.8, 128.7, 128.8, 129.3, 129.7, 135.1, 136.0, 164.2, 170.7. HRMS: m/z [M⁺] calcd for C₁₉H₁₇ClN₂O₂: 340.0979; found: 340.0986. 4-{(2E)-1-[(4-Fluorophenyl)amino]-3-phenylprop-2-en-1-yl}-2-methyl-1,3-oxazol-5(4H)-one (3d) Off-white solid; yield: 94.2 mg (82%); mp 170–172 °C. ¹H NMR (400 MHz, CDCl₃): δ = 2.03 (s, 3 H, CH₃), 4.62 (ddd, J _1,2 = 0.72, J _1,3 = 2.36, J _1,5 = 8.08 Hz, 1 H, H-2), 4.73 (dd, J _1,2 = 2.4, J _1,3 = 7.32 Hz, 1 H, H-1), 6.27 (dd, J _1,2 = 8.08, J _1,3 = 15.96 Hz, 1 H, H-3), 6.76 (d, J = 15.96 Hz, 1 H, H-4), 7.21 (d, J = 9.0 Hz, 2 H, Ar-H), 7.26–7.37 (m, 7 H, Ar-H). ¹³C NMR (100 MHz, CDCl₃): δ = 22.9, 62.7, 63.7, 118.6, 124.4, 126.8, 128.7, 128.8, 129.3, 129.7, 135.1, 135.4, 136.0, 164.2, 170.8. HRMS: m/z [M⁺] calcd for C₁₉H₁₇FN₂O₂: 324.1274; found: 324.1261.
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• 32 4,5-Dihydro-1H-imidazoles 5a–f; General Procedure A solution of the appropriate azetidinone 2 in anhyd MeOH (10 mL) was added to a stirred solution of NaOMe (2.0 equiv) in anhyd MeOH (5 mL), and the mixture was stirred at 80 °C for 6 h until the reaction was complete (TLC). The mixture was then concentrated and extracted with EtOAc (3 × 20 mL). The combined organic layers were dried over anhyd Na₂SO₄, filtered, and concentrated under vacuum to obtain a crude product that was purified by column chromatography [silica gel, EtOAc–hexane (10:90)].
• 33 Methyl 1-(4-Chlorophenyl)-2-methyl-5-[(E)-2-phenylvinyl]-4,5-dihydro-1H-imidazole-4-carboxylate (5c) Brown oil; yield: 84.5 mg (71%). ¹H NMR (500 MHz, CDCl₃): δ = 2.06 (s, 3 H, CH₃), 3.76 (s, 3 H, OCH₃), 4.48 (t, J = 4.90 Hz, 1 H, H-1), 4.95 (dd, J _1,2 = 4.95, J _1,3 = 7.30 Hz, 1 H, H-2), 6.07 (dd, J _1,2 = 6.35, J _1,3 = 15.86 Hz, 1 H, H-3), 6.62 (d, J = 15.7 Hz, 1 H, H-4), 6.67 (d, J = 8.55 Hz, 2 H, Ar-H), 7.14 (d, J = 8.60 Hz, 2 H, Ar-H), 7.32–7.35 (m, 5 H, Ar-H). ¹³C NMR (125 MHz, CDCl₃): δ = 23.2, 52.7, 55.8, 58.2, 114.9, 122.9, 125.8, 126.6, 128.0, 128.6, 129.1, 133.1, 136.0, 145.0, 170.3, 170.7. HRMS: m/z [M + H]⁺ calcd for C₂₀H₁₉ClN₂O₂: 355.1135; found: 355.1153.