References
-
1a
Levitzki A.
Gazit A.
Science
1995,
267:
1782
-
1b
Dixon RA.
Ferreira D.
Phytochemistry
2002,
60:
205
- 2
Traxler P.
Green J.
Mett H.
Séquin U.
Furet P.
J. Med. Chem.
1999,
42:
1018
-
3a
Stille JK.
Angew. Chem., Int.
Ed. Engl.
1986,
25:
508
-
3b
Farina V.
Krishnamurthy V.
Scott WJ.
Org.
React.
1997,
50:
1
-
4a
Miyaura M.
Yanagi T.
Suzuki A.
Synth. Commun.
1981,
11:
513
-
4b
Miyaura M.
Suzuki A.
Chem. Rev.
1995,
95:
2457
-
4c
Suzuki A.
J.
Organomet. Chem.
1999,
576:
147
-
5a
Zielske AG.
J. Org. Chem.
1987,
52:
1305
-
5b
Kotsuki H.
Kobayashi S.
Suenaga H.
Nishizawa H.
Synthesis
1990,
1145
-
5c
Schio L.
Lemoine G.
Klich M.
Synlett
1999,
1559
- 6
Kiely JS.
Laborde E.
Lesheski LE.
Bucsh RA.
J. Heterocycl.
Chem.
1991,
28:
1581
-
7a
Croisy M.
Huel C.
Bisagni E.
Heterocycles
1997,
45:
1683
-
7b Joseph B, Darro F, Guillaumet G, Kiss R, and Frydman A. inventors; PCT
Int. Appl., WO 0112607.
; Chem. Abstr. 2001, 134, 193348
- 8
Pelter A.
Ward RS.
Whalley JL.
Synthesis
1998,
1793
- 10
Carrera GM.
Sheppard GS.
Synlett
1994,
93
- 15
Bernotas RC.
Cube RV.
Synth. Commun.
1990,
20:
1209
-
16a
Garro-Helion F.
Merzouk A.
Guibé F.
J. Org. Chem.
1993,
58:
6109
-
16b
Jaime-Figueroa S.
Liu Y.
Muchowski JM.
Putman DG.
Tetrahedron
Lett.
1998,
39:
1313
- 17
Singh SB.
Tetrahedron
Lett.
1995,
36:
2009
- 19
Miki Y.
Hachiken H.
Kashima Y.
Sugimura W.
Yanase N.
Heterocycles
1998,
48:
1
9 Physical data of 4a:
mp 184-185 °C (EtOAc); IR (KBr): 1628, 1593, 1513
cm-1; 1H NMR (250
MHz, CDCl3): δ 3.76 (s, 3 H, NCH3),
3.81 (s, 3 H, OCH3), 3.94 (s, 3 H, OCH3), 6.71
(s, 1 H, Ar-H), 6.74 (s, 1 H, Ar-H), 6.89 (d, 2 H, J = 8.5 Hz,
Ar-H), 7.51 (d, 2 H, J = 8.5
Hz, Ar-H), 7.52 (s, 1 H, =CH); 13C
NMR (62.90 MHz, DMSO-d
6
): δ 41.2, 55.1, 56.4, 99.5,
106.7, 113.2, 113.4 (2), 121.1, 127.2, 129.8 (2), 143.0, 143.1,
149.0, 158.3, 160.9, 172.9; MS (IS): m/z 444 (MH+). Physical
data of 4b: mp 179-180 °C
(EtOAc); IR (KBr): 1630, 1610, 1592, 1560, 1515 cm-1; 1H
NMR (250 MHz, CDCl3): δ 3.78 (s, 3 H, NCH3),
3.93 (s, 3 H, OCH3), 4.05 (s, 3 H, OCH3),
6.85 (d, 2 H, J = 8.8 Hz, Ar-H),
6.98 (d, 1 H,
J = 8.8
Hz, Ar-H), 7.03 (d, 1 H, J = 8.8
Hz, Ar-H), 7.46 (s, 1 H, =CH), 7.53 (d, 2 H, J = 8.8 Hz, Ar-H); 13C
NMR (62.90 MHz, DMSO-d
6
): δ 46.3, 54.4, 55.6,
110.8, 112.8 (2), 116.1, 121.1, 122.4, 125.9, 128.9 (2), 132.7,
141.2, 143.6, 149.2, 158.0, 173.0; MS (IS): m/z 444
(MH+).
11 Typical procedure: To a solution of 4a (100 mg, 0.22 mmol) in anhyd 1,4-dioxane
(10 mL) was added freshly prepared tetrakis(triphenylphosphine)palladium
(17 mg, 0.014 mmol). The solution was stirred at r.t. for 30 min. Phenylboronic
acid (42 mg, 0.34 mmol) diluted in absolute EtOH (2 mL) was then
added, followed immediately by sat aq NaHCO3 (3 mL).
The heterogeneous solution was stirred at reflux for 3 h. After
cooling, palladium catalyst was removed by filtration. Brine solution
was then added, the two layers were separated and the aqueous phase
was extracted with EtOAc (3 × 5 mL). The combined organic extracts
were dried over MgSO4 and evaporated. The crude residue
was purified by flash chromatography on silica gel (CH2Cl2/EtOAc,
9:1) to afford 60 mg (71%) of 7a.
12 Typical procedure: A mixture of triflate 4a (200 mg, 0.45 mmol) and benzylamine
(0.24 mL, 2.20 mmol) in 1,4-dioxane (2 mL) was heated at 100 °C
for 6 h. After cooling, the solvent was evaporated. The crude residue
was purified by flash chromatography on silica gel (petroleum ether/EtOAc/NH4OH
4:6:0.1) to afford 150 mg (83%) of 9.
13 Physical data of 9:
mp 176-177 °C (EtOAc); IR (KBr): 3174, 1632, 1607,
1570, 1557, 1508, 1471 cm-1; 1H
NMR (250 MHz, CDCl3): δ 3.62 (s, 3 H, NCH3),
3.77 (s, 3 H, OCH3), 3.82 (s, 3 H, OCH3),
4.44 (d, 2 H, J = 5.6 Hz, CH2), 5.85
(s, 1 H, Ar-H), 5.87 (s, 1 H, Ar-H), 6.94 (d, 2 H, J = 8.8 Hz,
Ar-H), 7.22-7.33 (m, 3 H, Ar-H), 7.38-7.41 (m,
3 H, =CH + Ar-H), 7.48 (d, 2 H, J = 8.8
Hz, Ar-H), 11.02 (broad t, 1 H, J = 5.6
Hz, NH); 13C NMR (62.90 MHz, CDCl3): δ 41.6,
47.3, 55.2, 55.5, 85.2, 89.7, 108.1, 113.8 (2), 122.0, 127.1, 127.4
(2), 128.1, 128.7 (2), 130.2 (2), 138.8, 140.5, 144.4, 153.8, 158.8,
163.6, 178.9; MS (IS): m/z 401
(MH+); Anal. Calcd for C25H24N2O3:
C, 74.98; H, 6.04; N, 6.99. Found: C, 75.25; H, 5.89; N, 7.13.
14 All new compounds gave satisfactory
spectroscopic (1H NMR, 13C
NMR, MS and IR) and analytical data.
18 Physical data of 18:
mp 161-162 °C (EtOAc/petroleum ether);
IR (KBr): 3446, 3381, 1635, 1610, 1569, 1511 cm-1; 1H
NMR (250 MHz, CDCl3): δ 3.62 (s, 3 H, NCH3),
3.82 (s, 3 H, OCH3), 3.84 (s, 3 H, OCH3),
5.92 (d, 1 H, J = 2.2 Hz Ar-H),
5.98 (d, 1 H, J = 2.2 Hz, Ar-H),
6.94 (d, 2 H, J = 8.8 Hz, Ar-H),
7.11 (broad s, 2 H, NH2), 7.40 (s, 1 H, =CH),
7.49 (d, 2 H, J = 8.8 Hz, Ar-H); 13C
NMR (62.90 MHz, CDCl3): δ 41.5, 55.3, 55.5,
87.1, 93.8, 108.4, 113.8 (2), 121.8, 128.1, 130.2 (2), 140.9, 144.2,
153.7, 158.8, 163.2, 179.1; MS (IS): m/z 311
(MH+); Anal. Calcd for C18H18N2O3:
C, 69.66; H, 5.85; N, 9.03. Found: C, 70.01; H, 5.69; N, 8.92.