1026
C. M. Martı´nez-Viturro, D. Domı´nguez / Tetrahedron Letters 48 (2007) 1023–1026
(0.250 mL, 0.55 mmol) was added dropwise and the
References and notes
mixture was stirred under argon at room temperature
for 2 days. The solvent was evaporated and the residue
was purified by flash chromatography on silica gel (8:2,
hexanes–EtOAc), providing 10-phenylisoindolo[1,2-b]quin-
azolin-12(10H)-one (10f) as a white solid (0.123 g, 86%),
1. (a) Dzierzbicka, K.; Trzonkowski, P.; Sewerynek, P. L.;
Mysliwski, A. J. Med. Chem. 2003, 46, 978; (b) Guillau-
´
mel, J.; Leonce, S.; Pierre, A.; Renard, P.; Pfeiffer, B.;
Arimondo, P. B.; Monneret, C. Eur. J. Med. Chem. 2006,
41, 379; (c) Yilin, R.; Yun Feng, C.; Ting, C.; Chen, A. Y.;
Yu, C.; Liu, L. F.; Cheng, C. C. Pharm. Res. 1993, 10, 918.
2. Michael, J. P. Nat. Prod. Rep. 2005, 22, 627.
3. (a) Decker, M. Eur. J. Med. Chem. 2005, 40, 305; (b)
Anderskewitz, R.; Bauer, R.; Bodenbach, G.; Gester, D.;
Gramlich, B.; Morscha¨user, G.; Birke, F. W. Bioorg. Med.
Chem. Lett. 2005, 15, 669.
4. An alternative cyclisation based on an intramolecular
aza-Wittig reaction has been achieved: Eguchi, S.; Goto,
S. Heterocycl. Commun. 1994, 1, 51.
5. Kabbe, H. J. Justus Liebigs Ann. Chem. 1978, 398.
6. Meegalla, S. K.; Stevens, G. J.; McQueen, C. A.; Chen, A.
Y.; Yu, C.; Liu, L. F.; Barrows, L. R.; LaVoie, E. J. J.
Med. Chem. 1994, 37, 3434.
7. Rosevear, J.; Wilshire, J. F. K. Aust. J. Chem. 1990, 43,
339.
8. Mitsunobu, O. Synthesis 1981, 1.
9. Nguyen, P.; Corpuz, E.; Heidelbaugh, T. M.; Chow, K.;
Garst, M. E. J. Org. Chem. 2003, 68, 10195.
10. Typical procedure for the synthesis of isoindoloquinazol-
inones: To a deoxygenated solution of alcohol 8f (0.091 g,
0.46 mmol), phthalimide (0.083 g, 0.55 mmol) and PPh3
(0.146 g, 0.55 mmol) in dry THF (15 mL), DEAD
mp 206–208 ꢁC. IR (KBr): 1732, 1648 cmÀ1 1H NMR
.
(CDCl3, 300 MHz): d 8.08 (d, J = 7.6 Hz, 1H, ArH), 7.79
(d, J = 7.4 Hz, 1H, ArH), 7.69 (t, J = 7.4 Hz, 1H, ArH),
7.62 (d, J = 7.5 Hz, 1H, ArH), 7.56 (d, J = 8.0 Hz, 1H,
ArH), 7.37–7.12 (m, 7H, ArH), 7.08 (d, J = 7.6 Hz, 1H,
ArH), 6.32 (s, 1H, CH). 13C NMR/DEPT (CDCl3,
75 MHz): d 166.0 (CO), 148.9 (C), 142.2 (C), 139.8 (C),
134.6 (C), 133.1 (CH), 132.1 (CH), 130.4 (C), 128.81 (CH),
128.77 (2 · CH), 128.1 (CH), 128.0 (CH), 127.9 (2 · CH),
127.3 (2 · CH), 126.0 (C), 123.4 (CH), 122.2 (CH), 55.7
(CH). MS (CI), m/z (%): 339 ([M+C2H5]+, 23), 311
[M+H]+, 100), 310 (M+, 39), 233 ([MÀPh]+, 17). MS (EI),
m/z (%): 310 (M+, 14), 233 ([MÀPh]+, 100). HR-MS (EI):
Calcd for C21H14N2O, 310.1106. Found, 310.1100.
11. For the starting compounds, see: Adger, B. M.; Rees, C.
W.; Storr, R. C. J. Chem. Soc., Perkin Trans. 1 1975, 45,
[for (2-aminophenyl)(4-methoxyphenyl)methanone]; Hase-
gawa, H.; Muraoka, M.; Ohmori, M.; Matsui, K.; Kojima,
A. Bioorg. Med. Chem. 2005, 13, 3721, for (2-aminophe-
nyl)(3-methoxyphenyl)methanone.
12. For the starting (2-aminophenyl)(pyridine-2-yl)metha-
none, see: Fryer, R. I.; Zhang, P.; Rios, R. Synth.
Commun. 1993, 23, 985.