References
1 See: Hiroya K.
Suzuki N.
Yasuhara A.
Egawa Y.
Kasano A.
Sakamoto T.
J. Chem. Soc., Perkin Trans. 1
2000,
4339 ; and references cited therein
2a
Baldwin JE.
Thomas RC.
Kruse LI.
Silberman L.
J. Org. Chem.
1977,
42:
3846
2b
Johnson CD.
Acc. Chem. Res.
1993,
26:
476
3a
Castro CE.
Gaughan EJ.
Owsley DC.
J. Org. Chem.
1966,
31:
4071
3b
Sakamoto T.
Annaka M.
Kondo Y.
Yamanaka H.
Chem. Pharm. Bull.
1986,
34:
2754
3c
Nagarajan A.
Balasubramanian TR.
Indian J. Chem., Sect. B
1987,
26B:
917
3d
Nagarajan A.
Balasubramanian TR.
Indian J. Chem., Sect. B
1988,
27B:
380
3e
Tovar JD.
Swager TM.
J. Org. Chem.
1999,
64:
6499
For recent references, see:
4a
Liau H.-Y.
Cheng C.-H.
J. Org. Chem.
1995,
60:
3711
4b
Sashida H.
Kawamukai A.
Synthesis
1999,
1145
4c
Bellina F.
Ciucci D.
Vergamini P.
Rossi R.
Tetrahedron
2000,
56:
2533
4d
Rossi R.
Bellina F.
Biagetti M.
Catanese A.
Mannina L.
Tetrahedron Lett.
2000,
41:
5281
5a
Brown DW.
Mahon MF.
Ninan A.
Sainsbury M.
Shertzer HG.
Tetrahedron
1993,
49:
8919
5b Sainsbury M, and Shertzer HG. inventors; Eur. Pat. Appl. EP 91-309445 19911015.
5c
Shertzer HG.
Sainsbury M.
Food Chem. Toxicol.
1991,
29:
391
5d
Brown DW.
Graupner PR.
Sainsbury M.
Shertzer HG.
Tetrahedron
1991,
47:
4383
6
Estevez JC.
Estevez RJ.
Castedo L.
Tetrahedron Lett.
1993,
34:
6479
7
Sonogashira K.
Ohda Y.
Hagihara N.
Tetrahedron Lett.
1975,
4467
8 All new compounds gave satisfactory analytical and spectroscopic data. Selected physical and spectroscopic data follow. Compound 3a. Mp 90-91 °C(hexane). 1H NMR (ppm, CDCl3): δ = 3.96 (s, 3 H), 7.38-7.63 (m, 4 H), 7.71 (dd, J = 7.4 Hz, J = 0.9 Hz, 1 H), 7.78 (dd, J = 7.5 Hz, J = 1.2 Hz, 1 H), 7.99 (dd, J = 7.8 Hz, J = 0.9 Hz, 1 H), 8.06 (dd, J = 8.2 Hz, J = 0.9 Hz, 1 H). MS: m/z (%) = 262(1) [M+], 163(100). Compound 3b. Mp 110-113 °C(methanol). 1H NMR (ppm, CDCl3): δ = 3.96 (s, 6 H), 3.99 (s, 3 H), 7.14 (s, 1 H), 7.40 (t, J = 6.3 Hz, 1 H), 7.50 (t, J = 6.3 Hz, 1 H), 7.64 (s, 1 H), 7.70 (d, J = 7.5 Hz, 1 H), 7.80 (d, J = 7.5 Hz, 1 H). MS: m/z (%, CI) = 342(37) [M + 1]+, 312(100). Compound 3c. Mp 130-133 °C (methanol/dichloro-methane). 1H NMR (ppm, CDCl3): δ = 3.96 (s, 3 H), 3.97 (s, 3 H), 3.99 (s, 3 H), 7.16 (s, 1 H), 7.47 (t, J = 6.9 Hz, 1 H), 7.53 (s, 1 H), 7.62 (t, J = 6.9 Hz, 1 H), 7.81 (d, J = 7.8 Hz, 1 H), 8.10 (d, J = 8.2 Hz, 1 H). MS m/z (%) = 341(4) [M+], 223(100). Compound 7a. Mp 178-180 °C(chloroform). 1H NMR (ppm, CDCl3): δ = 4.67 (s, 0.5 H), 7.46 (dd, J = 7.9 Hz, J = 1.4 Hz, 1 H), 7.58 (td, J = 7.4 Hz, J = 1.3 Hz, 1 H), 7.72 (td, J = 7.4 Hz, J = 1.4 Hz, 1 H), 7.90-8.10 (m, 4 H), 8.21 (dd, J = 6.4 Hz, J = 1.4 Hz, 1 H). MS: m/z (%) = 267 (0.5) [M+], 104(100). Compound 7b. Mp 196-198 °C(methanol). 1H NMR (ppm, CDCl3): δ = 3.98 (s, 3 H), 4.02 (s, 3 H), 4.51 (s, 1 H), 6.82 (s, 1 H), 7.80 (s, 1 H), 7.90 (dd, J = 5.6 Hz, J = 3.1 Hz, 2 H), 8.04 (dd, J = 5.6 Hz, J = 3.4 Hz, 2 H). MS (FAB): m/z (%) = 327(9) [M + 1]+, 104(100). Compound 7c. Mp 210-213 °C (decomp., methanol/dichloromethane). 1H NMR (ppm, CDCl3): δ = 4.03 (s, 6 H), 4.74 (s, 1 H), 7.39-7.44 (m, 3 H), 7.55 (t, J = 7.8 Hz, 1 H), 7.68 (t, J = 7.4 Hz, 1 H), 8.15 (d, J = 8.1 Hz, 1 H). MS: m/z (%) = 327(10) [M+], 164(100). Compound 10a. Mp 242-245 °C(methanol). 1H NMR (ppm, CDCl3/CD3SOCD3): δ= 3.61 (s, 2 H), 7.01-7.20 (m, 3 H), 7.32 (t, J = 7.1 Hz, 1 H), 7.62 (m, 4 H), 11.51 (s, 1 H). MS (CI): m/z (%) = 246(17) [M + 1]+, 205(100). Compound 10b. Mp 205-207 °C (ethyl acetate/hexane). 1H NMR (ppm, CD3SOCD3): δ = 3.68 (s, 2 H), 3.94 (s, 3 H), 3.97 (s, 3 H), 6.96 (s, 1 H), 7.09 (s, 1 H), 7.16 (t, J = 7.5 Hz, 1 H), 7.30 (t, J = 7.5 Hz, 1 H), 7.40 (d, J = 7.5 Hz, 1 H), 7.51 (d, J = 7.2 Hz, 1 H), 8.17 (s, 1 H). MS (CI): m/z (%) = 265 [100) [M + 1]+. Compound 10c. Mp 245-250 °C (methanol/dichloro-methane). 1H NMR (ppm, CDCl3/CD3SOCD3): δ = 3.66 (s, 2 H), 3.96 (s, 3 H), 3.97 (s, 3 H), 7.06 (s, 1 H), 7.10-7.20 (m, 3 H), 7.40-7.44 (m, 1 H), 7.60-7.65 (m, 1 H), 8.30 (bs, 1 H). MS: m/z (%) = 265(100) [M+].
9
Steigel A.
Veith RW.
Braun M.
Liebigs Ann. Chem.
1989,
1:
99
10a
Cheng CC.
Structural Aspects of Antineoplastic Agents-A New Approach, In Progress in Medicinal Chemistry
Vol. 25:
Ellis GP.
West GB.
Elsevier Science Publisher, B. V. (Biomedical Division);
Amsterdam:
1988.
p.35
10b
Thomson RH.
Naturally Occurring Quinones
4th ed.:
Chapman and Hall;
London, New York:
1997.