B. kermark et al.
FULL PAPER
151.2, 144.0, 134.8, 133.3, 132.3, 130.6, 127.0, 126.6, 125.5, 121.1, 120.9, 111.2,
103.6, 55.8. C17H13NO3: calcd C 73.11, H 4.69; found C 73.16, H 4.80.
Queiroz, P. V. R. Shannon, J. Chem. Soc. Perkin Trans. 1, 1992, 3439 ±
3450.
Compound 3c: yield: 60%; The 1H NMR spectrum was in full accordance
with that reported in reference [28].
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Cyclization of 2-aryl-1,4-quinones
Compound 4a: The substrate (2 mmol, 100 mol%) and Pd(OAc)2
(22.4 mg, 0.1 mmol) were dissolved in glacial acetic acid (25 mL) and the
atmosphere was changed to oxygen. The mixture was stirred at 958C until
no starting material could be detected by TLC (approximately after 48 h).
Then the acetic acid was removed under reduced pressure and the residue
was purified by MPLC to give an 89% yield. The 1H NMR spectrum of 4a
was in full agreement with that reported in the literature.[29]
Compound 4b: Compound 4b was prepared according to the procedure
1
described above for 4a. 87% yield; H NMR (250 MHz, CDCl3): d 9.49
(brs, 1H), 8.26 (dd, 3J(H,H) 7.4 Hz, 3J(H,H) 1.4 Hz, 1H), 8.20 (dd,
3J(H,H) 7.4 Hz, 3J(H,H) 1.4 Hz, 1H), 7.96 (d, 3J(H,H) 8.0 Hz, 1H),
7.76 (td, 3J(H,H) 7.4 Hz, 3J(H,H) 1.4 Hz, 1H), 7.70 (td, 3J(H,H)
7.4 Hz, 3J(H,H) 1.4 Hz, 1H),7.31 (d, 3J(H,H) 8.0 Hz, 1H), 6.86 (d,
3J(H,H) 8.2 Hz, 1H), 4.02 (s, 3H); 13C NMR (400 MHz, [D6]DMSO): d
180.4, 177.1, 147.4, 136.9, 134.0, 133.9, 133.1, 132.7, 129.1, 125.9, 125.9, 125.4,
124.9, 117.8, 114.2, 106.6, 55.5. C17H11NO3: calcd C 73.64, H 4.00; found C
73.45, H 4.15.
Compound 4c: The same procedure was used as for compound 4a, such
that 86% of 4c was isolated. The 1H NMR spectrum was in full accordance
with that reported in reference [28].
Acknowledgments
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This work was supported by the Swedish Research Council for Engineering
Sciences and the Carl Trygger Foundation. H.H. and J.D.O. wish to thank
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Received: October 7, 1998
Revised version: February 25, 1999 [F1382]
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