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T. Bathini et al.
Letter
Synlett
be used to achieve selective N-arylation even in the pres-
ence of a hydroxyl group. Moreover, the catalytic system is
base- and ligand-free.
1996, 52, 8581. (c) Makaluvamines A and C: Radisky, D. C.;
Radisky, E. S.; Barrows, L. R.; Copp, B. R.; Kramer, R. A.; Ireland, C.
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Acknowledgment
(9) Mitchell, G.; Barnes, N. J.; Cox, J. M.; Matthews, I. R.; Parry, D. R.;
Pearson, D. P. J.; Smith, S. C. Synthesis and Chemistry of Agro-
chemicals VI, In ACS Symposium Series 800; Baker, D. R.; Fenyes,
J. G.; Lahm, G. P.; Selby, T. P.; Stevenson, T. M., Eds.; American
Chemical Society: Washington, D.C., 2001, Ch. 3 18–29.
(10) Hartwig, J. F. Angew. Chem. Int. Ed. 1998, 37, 2046.
(11) Klapars, A.; Antilla, J. C.; Huang, X.; Buchwald, S. L. J. Am. Chem.
Soc. 2001, 123, 7727.
T.B. and V.S.R. thank the University Grant Commission (UGC), New
Delhi for the award of research fellowships.
Supporting Information
Supporting information for this article is available online at
S
u
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p
ortiInfogrmoaitn
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p
p
ortioInfgrmoaitn
(12) Deng, W.; Wang, Y. F.; Zou, Y.; Liu, L.; Guo, Q.-X. Tetrahedron
Lett. 2004, 45, 2311.
(13) Klapars, A.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2002,
124, 7421.
References and Notes
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(2) (a) Dimmock, J. R.; Jha, A.; Zello, G. A.; Quail, J. W.; Oloo, E. O.;
Nienaber, K. H.; Kowalczyk, E. S.; Allen, T. M.; Santos, C. L.;
Clercq, E. D.; Balzarini, J.; Manavathu, E. K.; Stables, J. P. Eur. J.
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Giacobbe, R. A.; Tkacz, J. S.; Bills, G. F.; Liesch, J. M.; Zink, D. L.;
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(24) Typical Procedure: Aryl boronic acid (1.0 mmol), CuI (5 mol%),
amide (3.0 mmol), and DMSO (1.0 mL) were added to a reaction
vial, and the mixture was stirred at room temperature for
10 min. A 70% aqueous solution of TBHP (1.1 mmol) was added
to the reaction mixture dropwise over 5 min. The reaction vial
was then immersed in a preheated oil bath and the progress of
reaction was followed by TLC. Upon completion of reaction, the
cooled mixture was partitioned between water and ethyl ace-
tate. The aqueous layer was further extracted with ethyl ace-
tate, and the combined organic layers were washed with brine,
dried over Na2SO4, filtered, and concentrated in vacuo. The
residue was purified by column chromatography on silica gel
(hexane–ethyl acetate) to give the desired N-aryl lactam.
(25) 1-(4-Hydroxyphenyl)pyrrolidin-2-one (3a): Yield: 149 mg
(84%); dark-red solid; mp 165–167 °C (Lit.1 167 °C). IR (KBr):
3134, 2926, 1686, 1650, 1517, 1413, 1308, 1274, 1235, 1203,
(4) Coutrot, P.; Claudel, S.; Didierjean, C.; Grison, C. Bioorg. Med.
Chem. Lett. 2006, 16, 417.
(5) Baures, P. W.; Eggleston, D. S.; Erhard, K. F.; Cieslinski, L. B.;
Torphy, T. J.; Christensen, S. B. J. Med. Chem. 1993, 36, 3274.
(6) (a) Ho, B.; Crider, A. M.; Stables, J. P. Eur. J. Med. Chem. 2001, 36,
265. (b) Tiran, A. L.; Stables, J. P.; Kohn, H. Bioorg. Med. Chem.
2001, 9, 2693.
(7) (a) In the synthesis of benzo[a]quinazolidine-2-ones: Rubiralta,
M.; Diez, A.; Balet, A.; Bosch, J. Tetrahedron 1987, 43, 3021.
(b) Hexahydropyrido[3,4-c]-[1,5]benzothiazepines: Kumar, R.
R.; Perumal, S. Tetrahedron 2007, 63, 7850. (c) 5-(Diethoxy-
phosphoryl)-1-aryl-2-alkyl/aryl-2,3-dihydro-4-pyridones:
Commins, D. L.; Ollinger, C. G. Tetrahedron Lett. 2001, 42, 4115.
(d) 3-Aminopiperidines: Diez, A.; Voldoire, A.; Lopez, I.;
Rubiralta, M.; Segarra, V.; Pages, L.; Palacois, J. M. Tetrahedron
1995, 51, 5143. (e) Methyl indolo[2,3-a]quinazolidin-2-acetate:
Rubiralta, M.; Diez, A.; Vila, C.; Bettiol, J. L.; Troin, Y.; Sinibaldi,
M. E. Tetrahedron Lett. 1992, 33, 1233.
1220, 833, 657, 507, 460 cm–1
7.33 (d, 2 H, J = 9.0 Hz), 6.78 (d, 2 H, J = 8.8 Hz), 3.82 (t, J = 6.9,
7.1 Hz, 2 H), 2.61 (t, J = 7.9, 8.3 Hz, 2 H), 2.11–2.21 (m, 2 H). 13
.
1H NMR (300 MHz, CDCl3): δ =
C
NMR (75 MHz, CDCl3): δ = 174.5, 153.4, 131.7, 122.7, 115.7,
49.7, 32.3, 18.0. MS (ESI): m/z = 178 [M + H]+. HRMS (ESI): m/z
[M + H]+ calcd for C10H12O2N: 178.0862; found: 178.0863.
(8) (a) In the synthesis of guettardine and 15-epiguettardine: Diez,
A.; Tona, M.; Rubiralta, M. Tetrahedron 1990, 46, 4393. (b) (E)-
Azaburnamine: Lopez, I.; Diez, A.; Rubiralta, M. Tetrahedron
© Georg Thieme Verlag Stuttgart · New York — Synlett 2015, 26, 1348–1351