LETTER
Synthesis of Quinolone-Fused Multi-ring-Sized Heterocycles
2091
Scheme 3
(3) (a) Fürstner, A.; Langemann, K. Synthesis 1997, 792.
(b) Goldring, W. P. D.; Hodder, A. S.; Weiler, L.
Tetrahedron Lett. 1998, 39, 4955. (c) Dirat, O.; Vidal, T.;
Langlois, Y. Tetrahedron Lett. 1999, 40, 4801. (d) Hunt, J.
C. A.; Laurent, P.; Moody, C. J. Chem. Commun. 2000,
1771. (e) Crimmins, M. T.; King, B. W.; Zuercher, W. J.;
Choy, A. L. J. Org. Chem. 2000, 65, 8499. (f) Lane, C.;
Snieckus, V. Synlett 2000, 1294. (g) Boyer, F.-D.; Hanna,
I.; Nolan, S. P. J. Org. Chem. 2001, 66, 4094.
(h) Chatterjee, A. K.; Toste, F. D.; Goldberg, S. D.; Grubbs,
R. Pure Appl. Chem. 2003, 75, 421.
(4) (a) Joseph, B.; Darro, F.; Guillaumet, G.; Kiss, R.; Frydman,
A. PCT Int. Appl. WO 0112607, 2001; Chem. Abstr. 2001,
134, 193348. (b) Joseph, B.; Béhard, A.; Lesur, B.;
Guillaumet, G. Synlett 2003, 1542.
128.6 (CH), 128.2 (C), 125.7 (CH), 124.4 (C), 123.1 (C),
115.9 (C), 113.7 (2 CH), 91.7 (CH), 70.2 (CH2), 55.7 (CH3),
55.4 (CH3), 41.4 (CH3), 21.5 (CH2). MS (IS): m/z = 364
(M + H+). Anal. Calcd for C22H21NO4: C, 72.71; H, 5.82; N,
3.85. Found: C, 73.03; H, 5.94; N, 3.77.
(9) All new compounds gave satisfactory spectroscopic (1H-,
13C NMR, MS and IR) and analytical data.
(10) Physical data of compound 7: mp 119–120 °C (EtOAc). IR
(KBr): n = 3460, 1630, 1610, 1570, 1560, 1512 cm–1. 1H
NMR (250 MHz, CDCl3): d = 10.18 (broad s, 1 H, NH), 7.49
(d, 2 H, J = 7.8 Hz, Ar-H), 7.43 (s, 1 H, =CH), 6.93 (d, 2 H,
J = 7.8 Hz, Ar-H), 6.06 (s, 1 H, Ar-H), 6.17–5.89 (m, 2 H,
=CH), 5.34–5.25 (m, 1 H, =CH2), 5.08–4.95 (m, 3 H, =CH2),
3.90–3.82 (m, 5 H, OCH3 + CH2), 3.79 (s, 3 H, OCH3), 3.61
(s, 3 H, NCH3), 3.44–3.42 (m, 2 H, CH2). 13C NMR (62.90
MHz, CDCl3): d = 178.7 (CO), 162.0 (C), 158.6 (C), 154.9
(C), 142.1 (C), 140.2 (C), 137.9 (C), 137.2 (C), 130.1 (2
CH), 128.1 (CH), 121.8 (CH), 115.1 (CH2), 114.4 (CH2),
113.6 (2 CH), 112.0 (CH), 110.7 (C), 86.1 (CH), 55.4 (CH3),
55.3 (CH3), 51.4 (CH2), 41.5 (CH3), 30.2 (CH2). MS (IS):
m/z = 391 (M + H+). Anal. Calcd for C24H26N2O3: C, 73.82;
H, 6.71; N, 7.17. Found: C, 73.95; H, 6.60; N, 7.08.
(11) Physical data of compound 9: mp 245–246 °C (EtOAc). IR
(KBr): n = 1671, 1635, 1612, 1575, 1513 cm–1. 1H NMR
(250 MHz, CDCl3): d = 7.54 (s, 1 H, =CH), 7.50 (d, 2 H,
J = 8.7 Hz, Ar-H), 6.88 (d, 2 H, J = 8.7 Hz, Ar-H), 6.69 (s,
1 H, Ar-H), 5.75–5.68 (m, 1 H, =CH), 5.52–5.40 (m, 2 H,
CH2 + =CH), 3.98 (s, 3 H, OCH3), 3.81 (s, 3 H, OCH3), 3.78
(s, 3 H, NCH3), 3.63–3.43 (m, 3 H, CH2), 1.74 (s, 3 H,
COCH3). 13C NMR (62.90 MHz, CDCl3): d = 174.9 (CO),
169.5 (CO), 158.9 (C), 158.6 (C), 142.9 (C), 141.8 (C),
140.8 (CH), 130.1 (2 CH), 128.2 (C+CH), 127.7 (C), 124.2
(CH), 123.3 (C), 117.0 (C), 113.8 (2 CH), 95.6 (CH), 56.0
(CH3), 55.4 (CH3), 43.6 (CH2), 41.6 (CH3), 21.8 (CH3), 21.5
(CH2). MS (IS): m/z = 405 (M + H+). Anal. Calcd for
C24H24N2O4: C, 71.27; H, 5.98; N, 6.93. Found: C, 70.99; H,
6.12; N, 6.89.
(5) Chattopadhyay, S. K.; Maity, S.; Panja, S. Tetrahedron Lett.
2002, 43, 7781.
(6) (a) Ziegler, F. E. Chem. Rev. 1988, 88, 1423.
(b) Frauenrath, H. In Methods of Organic Chemistry
(Houben–Weyl), Stereoselective Synthesis, Vol. E21d;
Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E.,
Eds.; Thieme: Stuttgart, 1995, 3301–3756.
(7) Typical RCM Procedure: Under argon atmosphere,
Grubb’s reagent (19.6 mg, 0.02 mmol) was added to a
solution of 4a (93 mg, 0.24 mmol) in dry CH2Cl2 (10 mL).
The final solution was stirred at r.t. for 2 h. The solvent was
evaporated. The residue was purified by column
chromatography (petroleum ether–EtOAc, 2:8; then EtOAc)
to give 70 mg (81%) of 5a.
(8) Physical data of compound 5a: mp 175–176 °C (EtOAc). IR
(KBr): n = 1626, 1609, 1584, 1511 cm–1. 1H NMR (250
MHz, CDCl3): d = 7.52 (d, 2 H, J = 8.8 Hz, Ar-H), 7.42 (s,
1 H, =CH), 6.89 (d, 2 H, J = 8.8 Hz, Ar-H), 6.36 (s, 1 H, Ar-
H), 5.89–5.77 (m, 1 H, CH=), 5.51–5.45 (m, 1 H, CH=),
4.80–4.77 (m, 2 H, CH2), 3.90 (s, 3 H, OCH3), 3.80 (s, 3 H,
OCH3), 3.69 (s, 3 H, NCH3), 3.58–3.54 (m, 2 H, CH2). 13
C
NMR (62.90 MHz, CDCl3): d = 175.6 (CO), 159.7 (C),
158.7 (C), 158.6 (C), 141.6 (C), 140.4 (CH), 130.1 (2 CH),
Synlett 2003, No. 13, 2089–2091 © Thieme Stuttgart · New York