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3. No traces of aminothiazole 9g were detected in this case and only complex side products, whose characterization was difficult, were isolated.
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3. No traces of aminothiazole 9g were detected in this case and only complex side products, whose characterization was difficult, were isolated.
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0031942724
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68949136225
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Synthesis of 2-Aminothiazoles 9a-i; General Procedure: Alkyne 3, 6 or 7 (1.0 mmol) and the appropriate thiourea 8a-c (1.0 mmol) were suspended in anhyd DMF (1.0 mL) in a 10 mL glass vial equipped with a small magnetic stirring bar. K2CO3 (1.0 mmol) was then added to this solution and the mixture was irradiated under microwave conditions at 130 °C (2 x 5 min, using an irradiation power of 300 W. Microwave irradiations were conducted using a CEM Discover Synthesis Unit (CEM Corp, Matthews, NC, The mixture was then poured into H2O (10 mL) and then extracted with EtOAc (2 x 10 mL, The combined organic phases were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The crude products were purified by flash column chromatography SiO2; hexanes-EtOAc, 1:1, to yield the 2-aminothiazoles 9a-i as tan-colored oils
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2; hexanes-EtOAc, 1:1), to yield the 2-aminothiazoles 9a-i as tan-colored oils.
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22
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68949145628
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Characterization of 13a: 1H NMR (CDCl3, δ, 7.54 (s, 1 H, SCHCHCH3, 7.08-7.06 (m, 1 H, Ph, 6.75-6.71 (m, 2 H, Ph, 4.56-4.54 (m, 1 H, CH3CHPh, 2.34 (s, 3 H, NCCH3, 1.94 (s, 3 H, CH3, 1.58 (d, 3 H, CHCH3, 13C NMR (CDCl3, δ, 162.61, 160.13, 159.36, 151.22, 128.20, 128.00, 124.85, 119.38, 117.84, 111.64, 34.27, 17.88, 13.47, 10.35. MS (ESI, m/z, 321 [M, H, 343 [M, Na, Characterization of 13b: 1H NMR (CDCl3, δ, 7.08-7.04 (m, 1 H, Ph, 6.76-6.72 (m, 2 H, Ph, 6.27 (s, 1 H, SCHCHCH3, 4.54-4.49 (m, 1 H, CH 3CHPh, 2.70 (s, 3 H, NCCH3, 1.89 (s, 3 H, CH3, 1.58 (d, 3 H, CHCH3, 13C NMR CDCl3, δ, 162.63, 162.24, 160.14, 146.41, 135.98, 128.09
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