Solvent-Free Passerini Reactions
1125
61.6, 74.7, 169.5, 169.5, 169.8. Anal. calcd. for C10H17NO5: C, 51.94; H, 7.41;
N, 6.06. Found: C, 51.82; H, 7.46; N, 5.91, HRMS (ESI): m/z calcd. for
C10H17NO5Na [M þ Na]þ: 254.1004. Found: 254.0999.
Compound 4g: mp 44–46 8C. 1H NMR (200 MHz, CDCl3): d ¼ 0.94
(d, J ¼ 3.9 Hz, 6H), 1.29 (t, J ¼ 7.1 Hz, 3H), 1.71–1.98 (m, 3H), 2.16
(s, 3H), 4.01–4.05 (m, 2H), 4.22 (q, J ¼ 7.1 Hz, 2H), 5.25–5.52 (m, 1H),
6.71 (s, 1H). 13C NMR (50 MHz, CDCl3): d ¼ 14.6, 17.4, 19.2, 31.2, 41.5,
62.1, 78.4, 170.1, 170.2, 176.0. Anal. calcd. for C12H21NO5: C, 55.58; H,
8.16; N, 5.40. Found: C, 55.57; H, 8.34; N, 5.38. HRMS (ESI): m/z calcd.
for C12H21NO5Na [M þ Na]þ: 282.1317. Found: 282.1312.
1
Compound 4h: H NMR (200 MHz, CDCl3): d ¼ 0.87 (t, J ¼ 7.0 Hz, 3H),
1.25–1.32 (m, 15H), 1.85–2.05 (m, 2H), 2.17 (s, 3H), 4.01–4.07 (m, 2H),
4.22 (q, J ¼ 7.1 Hz, 2H), 5.20–5.37 (m, 1H), 6.61 (s, 1H). 13C NMR
(50 MHz, CDCl3): d ¼ 14.6, 14.6, 21.4, 23.1, 25.2, 29.5, 29.7, 32.2, 32.4,
41.5, 62.1, 74.4, 170.0, 170.1, 170.6. Anal. calcd. for C15H27NO5: C, 59.78;
H, 9.03; N, 4.65. Found: C, 59.61; H, 8.95; N, 4.63. HRMS (ESI): m/z
calcd. for C15H27NO5Na [M þ Na]þ: 324.1787. Found: 324.1798.
Compound 4i: The substrates were recovered instead.
1
Compound 4j: H NMR (200 MHz, CDCl3): d ¼ 1.28 (t, J ¼ 7.2 Hz, 3H),
3.81 (s, 3H), 4.08 (dd, J ¼ 3.6 Hz, J ¼ 4.9 Hz, 2H), 4.22 (q, J ¼ 7.1 Hz,
2H), 6.32 (s, 1H), 6.54 (s, 1H), 6.94 (d, J ¼ 8.8 Hz, 2H), 7.49
(d, J ¼ 8.8 Hz, 2H), 8.15–8.45 (m, 4H). 13C NMR (200 MHz, CDCl3):
d ¼ 14.5, 41.7, 55.7, 62.1, 76.6, 114.7, 123.9, 126.8, 129.7, 131.2, 163.6,
168.3, 169.7. Anal. calcd. for C20H20N2O8: C, 57.69; H, 4.84; N, 6.73.
Found: C, 57.72; H, 4.71; N, 6.73. HRMS (ESI): m/z calcd. for
C20H20N2O8Na [M þ Na]þ 439.1117. Found: 439.1126.
Compound 4k: 1H NMR (200 MHz, CDCl3 þ DMSO): d ¼ 1.16
(t, J ¼ 7.0 Hz, 3H), 3.96–4.02 (m, 2H), 4.16 (q, J ¼ 7.4 Hz, 2H), 6.51
(s, 1H), 7.9 (d, J ¼ 8.8 Hz, 2H), 8.26 (d, J ¼ 8.8 Hz, 2H), 8.30–8.38
(m, 4H). 13C NMR (200 MHz, CDCl3 þ DMSO): d ¼ 13.8, 60.9, 65.3,
74.8, 123.2, 123.3, 128.2, 130.8, 134.0, 141.7, 147.6, 150.3, 162.9, 167.0,
168.8. Anal. calcd. for C19H17N3O9: C, 52.90; H, 3.97; N, 9.74. Found: C,
53.05; H, 4.16; N, 9.53. HRMS (ESI): m/z calcd. for C19H17N3O9Na
[M þ Na]þ: 454.0862. Found: 454.0879.
1
Compound 4l: H NMR (200 MHz, CDCl3): d ¼ 1.28 (t, J ¼ 7.2 Hz, 3H),
4.09 (dd, J ¼ 4.0 Hz, J ¼ 4.9 Hz, 2H), 4.22 (q, J ¼ 7.1 Hz, 2H), 6.35
(s, 1H), 6.72 (s, 1H), 7.06–7.15 (m, 2H), 7.50–7.63 (m, 2H), 8.30–8.36
(m, 4H). 13C NMR (200 MHz, CDCl3): d ¼ 14.5, 41.7, 62.2, 76.1, 116.1,
116.6, 124.0, 130.0, 130.1, 130.7, 130.7, 131.2, 134.6, 151.1, 163.4, 167.9,
169.6. Anal. calcd. for C19H17FN2O7: C, 56.44; H, 4.24; N, 6.93. Found: C,
55.99; H, 4.56; N, 6.54. HRMS (ESI): m/z calcd. for C19H17FN2O7Na
[M þ Na]þ: 427.0917. Found: 427.0906.