Montmorillonite KSF clay catalyzed one-pot synthesis of a ...

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J. S. Yadav et al. / Tetrahedron 60 (2004) 1767–1771
4.2.6. Compound 3f. Yellow liquid, IR (KBr): n 34481,
2981, 2895, 2225, 1638, 1598, 1494, 1248, 1118, 1043, 923,
754. 1 H NMR (CDCl 3 ): d 1.37 (t, 3H, J¼6.9 Hz), 1.80 (brs,
1H, NH), 3.90 (AB q, 2H, J¼13.5 Hz), 4.15 (q, 2H, J¼
6.9 Hz), 4.80 (s, 1H), 6.30 (m, 1H), 6.87 (d, 1H, J¼8.0 Hz),
7.0 (t, 1H, J¼7.8 Hz), 7.30–7.45 (m, 4H). 13 C NMR (Proton
decoupled, CDCl 3 ): d 14.5, 43.9, 48.9, 63.8, 108.0, 110.1,
111.8, 118.6, 120.6, 122.7, 128.6, 130.3, 142.2, 151.6,
155.9. EIMS: m/z: 256 M þ , 227, 198, 173, 146, 120, 104,
95, 80, 52. HRMS calcd for C 15 H 16 N 2 O 2 : 256.12117.
Found: 256.12148.
4.2.7. Compound 3g. Pale yellow solid, mp 72–73 8C, IR
(KBr): n 3365, 2935, 2857, 2237, 1605, 1517, 1461, 1275,
1035, 791. 1 H NMR (CDCl 3 ): d 2.20 (s, 3H), 3.38 (brd, 1H,
NH, J¼8.1 Hz), 5.45 (d, 1H, J¼8.1 Hz), 6.80 (t, 2H, J¼
7.9 Hz), 7.10 (d, 1H, J¼8.0 Hz), 7.20 (d, 1H, J¼7.9 Hz),
7.40–7.50 (m, 3H), 7.50 (d, 2H, J¼8.0 Hz). 13 C NMR
(Proton decoupled, CDCl 3 ): d 17.8, 50.7, 112.2, 118.9,
120.4, 124.1, 127.7, 127.9, 129.8, 130.0, 131.3, 134.7,
143.4. EIMS: m/z: 222 M þ , 194, 155, 141, 116, 106, 91, 73,
65, 45. HRMS calcd for C 15 H 14 N 2 : 222.11569. Found:
222.11607.
4.2.8. Compound 3h. White crystalline solid, mp 95–
97 8C, IR (KBr): n 3410, 2931, 2230, 1610, 1520, 1461,
1269, 1051, 790. 1 H NMR (CDCl 3 ): d 4.65 (d, 1H, J¼
8.1 Hz), 5.45 (d, 1H, J¼8.1 Hz), 6.90–6.95 (m, 2H), 7.15–
7.35 (m, 4H), 7.58–7.65 (m, 2H). EIMS: m/z:260M þ , 234,
135, 100, 75. HRMS calcd for C 14 H 10 ClFN 2 : 260.05165.
Found: 260.05123.
4.2.9. Compound 3i. Yellow liquid, IR (KBr): n 3400,
2941, 2890, 2241, 1616, 1527, 1471, 1283, 1160, 1045, 789.
1 H NMR (CDCl 3 ): d 1.85 (brs, 1H, NH), 3.80 (s, 3H), 3.95
(AB q, 2H, J¼13.0 Hz), 4.70 (d, 1H, J¼13.0 Hz), 6.80–
6.95 (m, 3H), 7.25 (t, 1H, J¼7.9 Hz), 7.30–7.55 (m, 5H).
13 C NMR (Proton decoupled, CDCl 3 ): d 51.4, 53.6, 55.5,
96.5, 113.4, 114.2, 119.0, 120.9, 127.6, 129.3, 130.0, 135.3,
140.0, 160.2. EIMS: m/z: 252 M þ , 225, 122, 91, 77. HRMS
calcd for C 16 H 16 N 2 O: 252.12626. Found: 252.12661.
4.2.10. Compound 3j. Pale yellow oil, IR (KBr): n 3398,
2927, 2860, 2230, 1609, 1530, 1495, 1275, 1159, 1054, 787.
1 H NMR (CDCl 3 ): d 1.45 (d, 3H, J¼6.9 Hz), 1.95 (brs, 1H,
NH), 3.10–3.20 (m, 1H), 3.58–3.60 (m, 1H), 3.80 (d, 1H,
J¼13.0 Hz), 4.05 (d, 1H, J¼13.0 Hz), 7.20–7.45 (m, 10H).
EIMS: m/z: 250 M þ , 223, 145, 105, 91, 77, 51. HRMS calcd
for C 17 H 18 N 2 : 250.14699. Found: 250.14659.
4.2.11. Compound 3k. Yellow liquid, IR (KBr): n 3306,
2923, 2851, 2225, 1691, 1575, 1462, 1216, 1141, 1017, 940,
765. 1 H NMR (CDCl 3 ): d 1.80 (brs, 1H, NH), 4.0 (s, 2H),
4.78 (s, 1H), 6.20–6.40 (m, 2H), 7.30–7.55 (m, 6H). EIMS:
m/z: 212 M þ , 186 105, 81, 77 51, 39. HRMS calcd for
C 13 H 12 N 2 O: 212.09496. Found: 212.09523.
4.2.12. Compound 3l. Light brown solid, mp 99–100 8C,
IR (KBr): n 3400, 2967, 2895, 2235, 1601, 1535, 1482,
1280, 1180, 1055, 791. 1 H NMR (CDCl 3 ): d 1.60 (d, 3H,
J¼6.9 Hz), 3.20–3.37 (m, 1H), 3.45–3.55 (m, 1H), 4.30–
4.45 (m, 1H)), 6.65 (d, 2H, J¼8.0 Hz), 6.85 (t, 1H, J¼
7.9 Hz), 7.20–7.45 (m, 7H). EIMS: m/z: 236 M þ , 209, 131,
105, 77, 51. HRMS calcd for C 16 H 16 N 2 : 236.13134. Found:
236.13178.
4.2.13. Compound 3m. Pale yellow solid, mp 117–119 8C,
IR (KBr): n 3350, 2929, 2233, 1603, 1505, 1461, 1275,
1030, 976, 897, 746. 1 H NMR (CDCl 3 ): d 3.80 (d, 1H, J¼
8.1 Hz), 5.05 (m, 1H), 6.30 (dd, 1H, J¼6.9, 17.3 Hz), 6.78
(d, 1H, J¼8.0 Hz), 6.90 (t, 1H, J¼7.9 Hz), 7.08 (dd, 1H,
J¼1.7, 17.3 Hz), 7.25–7.45 (m, 8H). EIMS: m/z: 234 M þ ,
206, 128, 115, 77, 51. HRMS calcd for C 16 H 14 N 2 :
234.11569. Found: 234.11515.
4.2.14. Compound 3n. Pale yellow liquid, IR (KBr): n
3405, 2925, 2854, 2235, 1600, 1505, 1463, 1279, 1160,
1030, 791. 1 H NMR (CDCl 3 ): d 0.90 (t, 3H, J¼6.8 Hz),
1.20–1.40 (m, 12H), 1.50–1.65 (m, 2H), 1.80–1.90 (m,
2H), 3.80 (brs, NH), 4.05–4.15 (m, 1H), 6.60 (d, 2H, J¼
8.0 Hz), 6.80 (t, 1H, J¼7.9 Hz), 7.20 (t, 2H, J¼7.9 Hz). 13 C
NMR (Proton decoupled, CDCl 3 ): d 48.9, 112.7, 116.3,
116.6, 117.5, 120.4, 120.5, 127.9, 129.0, 129.1, 129.6,
140.4, 161.6, 164.9. EIMS: m/z: 258 M þ , 185, 155, 135,
121, 77, 51. HRMS calcd for C 17 H 26 N 2 : 258.20959. Found:
258.20906.
4.2.15. Compound 3o. Brown solid, mp 93–94 8C, IR
(KBr): n 3364, 2924, 2855, 2233, 1599, 1499, 1406, 1271,
1239, 1127, 1035, 979, 866, 750. 1 H NMR (CDCl 3 ): d 3.90
(brs, 1H, NH), 5.60 (s, 1H), 6.0 (s, 2H), 6.70 (d, 2H, J¼
8.0 Hz), 6.90 (t, 1H, J¼7.9 Hz), 7.08 (m, 1H), 7.20–7.45
(m, 3H). EIMS: m/z: 331 M þ , 305, 282, 249, 229, 199, 155,
141, 97, 69, 51, 39. HRMS calcd for C 15 H 11 BrN 2 O 2 :
330.00038. Found: 330.00108.
4.2.16. Compound 3p. Dark brown solid, mp 68–70 8C, IR
(KBr): n 3359, 2925, 2235, 1695, 1601, 1501, 1440, 1289,
1248, 1149, 1014, 880, 751. 1 H NMR (CDCl 3 ): d 4.05 (d,
1H, J¼8.1 Hz), 5.40 (d, 1H, J¼8.1 Hz), 6.40 (m, 1H), 6.55
(m, 1H), 6.80 (d, 2H, J¼8.0 Hz), 6.90 (t, 1H, J¼7.9 Hz),
7.25 (t, 2H, J¼7.9 Hz), 7.40 (m, 1H). EIMS: m/z: 198 M þ ,
169, 155, 141, 115, 106, 92, 77, 51. HRMS calcd for
C 12 H 10 N 2 O: 198.07931. Found: 198.07890.
4.2.17. Compound 3q. Yellow solid, mp 76–78 8C, IR
(KBr): n 3306, 2923, 2851, 2225, 1691, 1575, 1462, 1216,
1141, 1017, 940, 765. 1 H NMR (CDCl 3 ): d 2.40 (s, 3H),
3.90 (d, J¼8.1 Hz), 5.40 (d, J¼8.1 Hz), 6.78 (d, 2H, J¼
8.0 Hz), 6.90 (t, 1H, J¼7.8 Hz), 7.20–7.30 (m, 4H), 7.50 (d,
2H, J¼8.0 Hz), 7.50 (d, 2H, J¼8.0 Hz). EIMS: m/z: 222
M þ , 194, 176, 131, 103, 91, 77 41. HRMS calcd for
C 15 H 14 N 2 : 222.11569. Found: 222.11508.
Acknowledgements
B. V. S. thanks CSIR, New Delhi, for the award of
fellowships.
References and notes
1. Shafran, Y. M.; Bakulev, V. A.; Mokrushin, V. S. Russ. Chem.
Rev. 1989, 58, 148.