N. Zanatta et al. / Tetrahedron Letters 45 (2004) 5689–5691
5691
3
3
9. Jiang, B.; Zang, F.; Xiong, W. Tetrahedron Lett. 2002, 43,
665.
10. Silva, G. V. J.; Pelisson, M. M. M.; Constantino, M. G.
Tetrahedron Lett. 1994, 35, 7327.
11. Tius, M. A.; Savariar, S. Tetrahedron Lett. 1985, 26, 3638.
12. Colla, A.; Martins, M. A. P.; Clar, G.; Krimmer, S.;
Fischer, P. Synthesis 1991, 483.
13. Flores, A. F. C.; Zanatta, N.; Rosa, A.; Brondani, S.;
Martins, M. A. P. Tetrahedron Lett. 2002, 43, 5005.
14. Madruga, C. C.; Clerici, E.; Martins, M. A. P.; Zanatta,
N. J. Heterocycl. Chem. 1995, 32, 735.
15. Zanatta, N.; Cortelini, M. F. M.; Carpes, M. J. S.;
Bonacorso, H. G.; Martins, M. A. P. J. Heterocycl. Chem.
1997, 34, 509.
16. Zanatta, N.; Fagundes, M. B.; Ellenshon, R.; Marques,
M.; Bonacorso, H. G.; Martins, M. A. P. J. Heterocycl.
Chem. 1998, 35, 451.
17. Zanatta, N.; Barichello, R.; Tramontina, R.; Bonacorso,
H. G.; Martins, M. A. P. Tetrahedron Lett. 2003, 44, 961.
18. Mainard-Faure, P.; Gonser, C.; Vaime, V.; Bouchu, D.
Tetrahedron Lett. 1998, 39, 2315.
(dd, 1H, JH5–H4 ¼ 1:3, JH5–H2 < 1:0 Hz, H-5), 7.97 (dd,
1H, JH2–H4 < 1:0, JH2–H5 < 1:0 Hz, H-2). 13C NMR
(50 MHz, CDCl3): d 51.3 (–CH2–), 73.0 (BCH), 77.1
(–CB), 109.1 (C-4), 117.9 (C-3), 143.3 (C-5), 147.6 (C-2),
166.8 (C@O). GCMS (EI, 70 e V) m=z (%): 150 (Mþ, 100),
95 (92).
3
3
1
3f: H NMR (CDCl3, 200 MHz): d 5.28 (s, 2H, –CH2–),
3
6.75 (d, 1H, JH4–H5 ¼ 2Hz, H-4), 7.33–7.39 (m, 6H, H-5,
Ph), 8.02(d, 1H, J < 1:0 Hz, H-2). 13C NMR (50 MHz,
CDCl3): d 66.1 (–CH2–), 109.8 (C-4), 128.0, 128.1, 128.4,
135.9 (Ph), 143.7 (C-5), 147.8 (C-2), 162.8 (C@O).
GCMS (EI, 70 e V) m=z (%): 202 (Mþ, 2 4), 184 (14), 95
(100).
3g: 1H NMR (CDCl3, 200 MHz): d 6.91 (s, 1H, H-4), 7.23
(br s, 2H, NH2), 7.70 (s, 1H, H-5), 8.18 (s, 1H, H-2). 13C
NMR (50 MHz, CDCl3): d 109.3 (C-4), 122.9 (C-3), 144.0
(C-5), 145.3 (C-2), 163.4 (C@O). GCMS (EI, 70 eV) m=z
(%): 111 (Mþ, 60), 95 (100).
3h: 1H NMR (CDCl3, 200 MHz):
d 2.89 (d, 3H,
J ¼ 4:4 Hz, NMe) 6.91 (s, 1H, H-4), 7.23 (br s, 1H,
NH), 7.70 (s, 1H, H-5), 8.18 (s, 1H, H-2). 13C NMR
(50 MHz, CDCl3): d 25.8 (NMe) 109.3 (C-4), 122.9 (C-3),
144.0 (C-5), 145.3 (C-2), 163.4 (C@O). GCMS (EI, 70 eV)
m=z (%): 111 (Mþ, 60), 95 (100).
19. Handbook of Fine Chemicals and Laboratory Equipment:
Aldrich; 2003–2004, p 940.
20. Following are 1H NMR and 13C NMR, and GCMS
spectral data of compounds: 2: 1H NMR (CDCl3,
3i: 1H NMR (200 MHz, CDCl3): d 3.88–3.93 (m; 2H,
CH2), 5.01–5.16 (m, 2H, @CH2), 5.70–5.88 (m, 1H, @CH),
3
4
200 MHz): d 6.96 (dd, 1H, JH4–H5 ¼ 1:4 Hz, JH4–H2
<
<
<
3
4
3
1:0 Hz, H-4), 7.50 (dd, 1H, JH5–H4 ¼ 1:4 Hz, JH5–H2
6.63 (d, 1H, JH4–H5 ¼ 1:7 Hz, H-4), 6.70 (br s, 1H, NH),
3
4
3
1:0 Hz, H-5), 8.36 (dd, 1H, JH2–H4 ¼; 1:0 Hz, JH2–H5
7.33 (d, 1H, JH5–H4 ¼ 1:7 Hz, H-5), 7.91 (s, 1H, H-2). 13C
1:0 Hz, H-2). 13C NMR (50 MHz, CDCl3): d 95.4 (CCl3),
110.9 (C-4), 118.3 (C-3), 143.7 (C-5), 150.6 (C-2), 176.4
(C@O). GCMS (EI, 70 eV) m=z (%): 213 (Mþ, 3), 149 (10),
95 (100). Anal. Calcd for C6H3Cl3O2 (213.44): C, 33.76; H,
1.42. Found: C, 33.58; H, 1.63.
NMR (50 MHz, CDCl3): d 41.8 (CH2), 108.4 (C-4), 116.3
(@CH2), 122.4 (C-3), 134.0 (@CH), 143.6 (C-5), 144.8 (C-
2), 162.7 (C@O). MF (MW): C8H9NO2 (151.16). GCMS
(EI, 70 eV) m=z (%): 151 (Mþ, 6), 122 (10), 95 (100).
3j: 1H NMR (CDCl3, 200 MHz): d 4.44 (s, 2H, –NH2),
3a: 1H NMR (200 MHz, CDCl3):
d
6.78 (d, 1H,
6.89–6.90 (dd, 1H, JH4–H5 ¼ 1:7 Hz, JH4–H2 < 1:0 Hz H-
3
4
3JH4–H5 ¼ 1:3 Hz, H-4), 7.45 (d, 1H, JH5–H4 ¼ 1:3 Hz, H-
4), 7.76–7.75 (dd, 1H, JH5–H4 ¼ 1:7 Hz, JH2–H5 < 1:0 Hz,
H-5), 8.19–8.20 (t, 1H, J < 1:0 Hz, H-2), 9.60 (br s, 1H,
NH). 13C NMR (50 MHz, CDCl3): d 108.6 (C-4), 121.3 (C-
3), 142.8 (C5), 144.7 (C-2), 161.5 (C@O).
3
3
4
3
5), 8.12(d, 1H, JH2–H4 < 1:0 Hz, H-2), 11.03 (s, 1H, OH).
13C NMR (50 MHz, CDCl3): d 110.1 (C-4), 119.0 (C-3),
144.3 (C-5), 149.4 (C-2), 169.16 (C@O). GCMS (EI, 70 eV)
m=z (%): 112(M þ, 100), 95 (92).
1
3k: H NMR (200 MHz, CDCl3): d 1.59 (m, 6H, –CH2–),
3b: 1H NMR (CDCl3, 200 MHz): d 3.83 (s, 3H, OCH3),
3.40 (m, 4H, –N–CH2–), 6.45 (d, 1H, 3JH4–H5 ¼ 1:2Hz, H-
3
3
3
6.74 (d, 1H, JH4–H5 ¼ 1:3 Hz H-4), 7.43 (d, 1H, JH5–H4
¼
4), 7.34 (d, 1H, JH5–H4 ¼ 1:2Hz, H-5), 7.60 (s, 1H, H-2).
1:3 Hz, H-5), 8.02(s, 1H, H-)2.
13C NMR (50 MHz,
13C NMR (50 MHz, CDCl3): d 24.3 (–CH2–), 48,1 (–N–
CH2–), 108.9 (C-4), 121.1 (C-3), 142.5 (C-5), 142.8 (C-2),
163.4 (C@O).
CDCl3): d 51.4 (OCH3), 109.6 (C-4), 119.1 (C-3), 143.6 (C-
5), 147.6 (C-2), 163.4 (C@O).
3c: 1H NMR (200 MHz, CDCl3):
d
1.25 (t, 3H,
3l: H NMR (200 MHz, CDCl3): d 3.61 (m, 8H, O–CH2–
1
3J ¼ 7:1 Hz, CH3), 4.21 (q, 2H, 3J ¼ 7:1 Hz, OCH2),
CH2-N), 6.47 (d, 1H, JH4–H5 ¼ 1:3 Hz, H-4), 7.36 (d, 1H,
3
3
4
6.65 (dd, 1H, JH4–H5 ¼ 1:3 Hz, JH4–H2 < 1:0 Hz, H-4),
3JH5–H4 ¼ 1:3 Hz, H-5), 7.64 (s, 1H, H-2). 13C NMR
(50 MHz, CDCl3): d 66.7 (O–CH2–CH2–N), 109.9 (C-4),
120.5 (C-3), 143.0 (C-5), 143.5 (C-2), 163.8 (C@O).
3m: 1H NMR (CDCl3, 200 MHz): d 6.93 (s, 1H, H-4),
7.23–7.14 (m, 6H, –Ph, N–H), 7.45 (s, 1H, H-5), 8.33 (s,
1H, H-2). 13C NMR (50 MHz, CDCl3): d 110.5 (C-4),
119.5 (C-3), 124.9, 127.8, 128.6, 137.4 (Ph), 143.3 (C-5),
150.2(C-2), 176.0 (C @O).
3
7.34 (d, 1H, JH5–H4 ¼ 1:3 Hz, H-5), 7.93 (dd, 1H,
4
3JH2–H4 < 1:0 Hz, JH2–H5 < 1:0 Hz, H-2). 13C NMR
(50 MHz, CDCl3): d 14.0 (CH3), 60.2(OCH ), 109.6 (C-
2
4), 119.4 (C-3), 143.5 (C-5), 147.4 (C-2), 162.9 (C@O).
3d: 1H NMR (CDCl3, 200 MHz):
d 4.75 (d, 2H,
J ¼ 5:6 Hz, –CH2–), 5.25–5.42 (m, 2H, @CH2), 5.89–6.07
(m, 1H, @CH), 6.76 (s, 1H, H-4), 7.43 (s, 1H, H-5), 8.04 (s,
1H, H-2). 13C NMR (50 MHz, CDCl3): d 64.9 (OCH2),
109.7 (C-4), 118.0 (C-3), 119.1 (@CH2), 132.0 (CH@),
143.6 (C-5), 147.5 (C-2), 162.6 (C@O). GCMS (EI, 70 e V)
m=z (%): 152(M þ, 6), 95 (100).
3n: 1H NMR (CDCl3, 200 MHz):
d 4.57 (d, 2H,
J ¼ 6:0 Hz, –CH2–), 6.62(s, 1H, H-4), 7.27–7.39 (s, 6H,
Ph, NH), 7.41 (s, 1H, H-5), 7.94 (s, 1H, H-2). 13C NMR
(50 MHz, CDCl3): d 43.0 (–CH2–), 108.0 (C-4), 122.0 (C-
3), 127.0–128.2, 137.9 (–Ph), 143.2 (C-5), 144.6 (C-2),
162.3 (C@O). GCMS (EI, 70 e V) m=z (%): 201(Mþ, 39),
172(13), 95 (100).
3e: 1H NMR (CDCl3, 200 MHz):
d 2.46 (t, 1H,
4J ¼ 2:4 Hz, BCH), 4.76 (d, 2H, 4J ¼ 2:4 Hz, –CH2–),
3
3
6.67 (dd, 1H, JH4–H5 ¼ 1:3, JH4–H2 < 1:0 Hz, H-4), 7.35