H
S. Mirzaei et al.
Paper
Synthesis
1H NMR (500.1 MHz, CDCl3): δ = 3.92 (s, 3 H, OCH3), 6.86 (d, J = 2.3 Hz,
1 H), 6.91 (dd, J = 8.7, 2.4 Hz, 1 H), 7.48 (t, J = 7.8 Hz, 2 H), 7.50 (d, J =
8.7 Hz, 1 H), 7.60 (tt, J = 7.4, 1.2 Hz, 1 H), 7.85 (dd, J = 8.2, 1.1 Hz, 2 H),
8.09 (s, 1 H).
(13) Bonsignore, L.; Loy, G.; Secci, D.; Calignano, A. Eur. J. Med. Chem.
1993, 28, 517.
(14) (a) Augustine, R. L. Carbon–Carbon Bond Formation, Dekker. Ed.;
New York, 1979; Vol. 1. (b) Bunceland, E.; Durst, T. Comprehen-
sive Carbanion Chemistry, Part B; Elsevier: Amsterdam, 1984.
(c) Trost, B. M.; Fleming, I. Comprehensive Organic Synthesis, Per-
gamon, Ed.; Oxford, 1991, Vol. 3.
3-Benzoyl-6-bromo-2H-chromen-2-one (5e)28f
Isolated yield: 0.077 g (78%); white solid; m.p. 173–175 °C [lit. 177.8–
178.7 °C].
(15) (a) Brown, J. M.; Cooley, N. A. Chem. Rev. 1988, 88, 1031. (b) Li,
C.-J. Chem. Rev. 1993, 93, 2023.
IR (KBr): 3073, 1717, 1658, 1563, 1239, 828 cm–1
.
(16) (a) Meijere, A. D.; Diederich, F. Metal-Catalyzed Cross-Coupling
Reactions, 2nd ed.; Wiley-VCH: Weinheim, 2004. (b) Luh, T.-Y.;
Leung, M.-K.; Wong, K.-T. Chem. Rev. 2000, 100, 3187.
(17) (a) Tsuji, J. Palladium Reagents and Catalysts: Innovations in
Organic Synthesis; Wiley: Chichester, 1995. (b) Seechurn, C. C. C.
J.; Kitching, M.; Colacot, O.; Snieckus, V. Angew. Chem. Int. Ed.
2012, 51, 5062. (c) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95,
2457.
1H NMR (500.1 MHz, CDCl3): δ = 7.99 (s, 1 H), 7.87 (dd, J = 7.3, 1.2 Hz,
2 H), 7.70–7.76 (m, 2 H), 7.63 (t, J = 7.4 Hz, 1 H), 7.49 (t, J = 7.8 Hz,
2 H), 7.30 (d, J = 8.6 Hz, 1 H).
Funding Information
(18) (a) Beller, M.; Wu, X.-F. Transition-Metal Catalyzed Carbonyla-
tion Reactions: Carbonylative Activation of C–X Bonds; Springer:
Amsterdam, 2013. (b) Beller, M. Catalytic Carbonylation Reac-
tions; Springer: Berlin, 2006. (c) Kollär, L. Modern Carbonylation
Methods; Wiley-VCH: Weinheim, 2008. (d) Liang, Z.; Zhang, J.;
Liu, Z.; Wang, K.; Zhang, Y. Tetrahedron 2013, 69, 6519.
(e) Konishi, H.; Manabe, K. Synlett 2014, 25, 1971. (f) Dong, K.;
Sang, R.; Liu, J.; Razzaq, R.; Franke, R.; Jackstell, R.; Beller, M.
Angew. Chem. Int. Ed. 2017, 56, 1.
We acknowledge the financial support from the SOHA pharmaceuti-
cal company and University of Tehran.()
Supporting Information
Supporting information for this article is available online at
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(19) (a) Tsuji, J.; Morikawa, M.; Iwamoto, N. J. Am. Chem. Soc. 1964,
86, 2095. (b) Tsuji, J.; Takahashi, M.; Takahashi, T. Tetrahedron
Lett. 1980, 21, 849. (c) Yamamoto, Y. Adv. Synth. Catal. 2010,
352, 478. (d) Zhou, Q. J.; Worm, K.; Dolle, R. E. J. Org. Chem. 2004,
69, 5147. (e) Guan, Z.-H.; Chen, M.; Ren, Z.-H. J. Am. Chem. Soc.
2012, 134, 17490. (f) Ferguson, J.; Zeng, F.; Alwis, N.; Alper, H.
Org. Lett. 2013, 15, 1998. (g) Baburajan, P.; Elango, K. P. Tetrahe-
dron Lett. 2014, 55, 3525. (h) Kadnikov, D. V.; Larock, R. C. Org.
Lett. 2000, 2, 3643. (i) Takács, A.; Marosvölgy-Hasko, D.; Kabak-
Solt, Z.; Damas, L.; Rodrigues, F. M. S.; Carrilho, R. M. B.; Pineiro,
M.; Pereira, M. M.; Kollár, L. Tetrahedron 2016, 72, 247. (j) Han,
W.; Jin, F.; Zhou, Q. Synthesis 2015, 47, 1861. (k) Tjutrins, J.;
Arndtsen, B. A. J. Am. Chem. Soc. 2015, 137, 12050. (l) Wu, X.-F.;
Anbarasan, P.; Neumann, H.; Beller, M. Angew. Chem. Int. Ed.
2010, 49, 7316.
(20) (a) Martinelli, J. R.; Freckmann, D. M.; Buchwald, S. L. Org. Lett.
2006, 8, 4843. (b) Martinelli, J. R.; Clark, T. P.; Watson, D. A.;
Munday, R. H.; Buchwald, S. L. Angew. Chem. Int. Ed. 2007, 46,
8460. (c) Zhang, S.; Wang, L.; Feng, X.; Bao, M. Org. Biomol.
Chem. 2014, 12, 7233. (d) Zhang, C.; Liu, J.; Xia, C. Org. Biomol.
Chem. 2014, 12, 9702. (e) Chen, J.; Natte, K.; Spannenberg, A.;
Neumann, H.; Beller, M.; Wu, X.-F. Org. Biomol. Chem. 2014, 12,
5578.
References
(1) Murray, R. D. H. Prog. Chem. Org. Nat. Prod. 2002, 83, 1.
(2) Gao, S.; Tsai, C. H.; Tseng, C.; Yao, C.-F. Tetrahedron 2008, 64,
9143.
(3) (a) Belluti, F.; Fontana, G.; Bo, L.; Carenini, N.; Giommarelli, C.;
Zunino, F. Bioorg. Med. Chem. 2010, 18, 3543. (b) Riveiro, M. E.;
Moglioni, A.; Vazquez, R.; Gomez, N.; Facorro, G.; Piehl, L.; de
Celis, E. R.; Shayo, C.; Davio, C. Bioorg. Med. Chem. 2008, 16,
2665.
(4) Tanabe, A.; Nakashima, H.; Yoshida, O.; Yamamoto, N.; Tenmyo,
O.; Oki, T. J. Antibiot. 1988, 41, 1708.
(5) (a) Fylaktakidou, K. C.; Hadjipavlou-Litina, D. J.; Litinas, K. E.;
Nicolaides, D. N. Curr. Pharm. Des. 2004, 10, 3813. (b) Roussaki,
M.; Kontogiorgis, C.; Hadjipavlou-Litina, D. J.; Hamilakis, S.
Bioorg. Med. Chem. Lett. 2010, 20, 3889.
(6) Morgan, L. R.; Jursic, B. S.; Hooper, C. L.; Neumann, D. M.;
Thangaraj, K.; Leblance, B. Bioorg. Med. Chem. Lett. 2002, 12,
3407.
(7) Vilar, S.; Quezada, E.; Santana, L.; Uriarte, E.; Yanez, M.; Fraiz, N.;
Alcaide, C.; Cano, E.; Orallo, F. Bioorg. Med. Chem. Lett. 2006, 16,
257.
(8) Kostova, I. Curr. HIV Res. 2006, 4, 347.
(21) Rahman, O.; Kihlberg, T.; Långström, B. J. Org. Chem. 2003, 68,
3558.
(9) (a) Chilin, A.; Battistutta, R.; Bortolato, A.; Cozza, G.; Zanatta, S.;
Poletto, G.; Mazzorana, M.; Zagotto, G.; Uriarte, E.; Guiotto, A.;
Meggio, F.; Moro, S. J. Med. Chem. 2008, 51, 752. (b) Zhou, X.;
Wang, X. B.; Wang, T.; Kong, L. Y. Bioorg. Med. Chem. 2008, 16,
8011.
(10) Balaji, P. N.; Lakshmi, L. K.; Mohan, K.; Revathi, K.;
Chamundeswari, A.; Indrani, P. M. Der Pharmacia Sinica 2012, 3,
685.
(11) Morgan, L. R.; Jursic, B. S.; Hooper, C. L.; Neumann, D. M.;
Thangaraj, K.; Leblance, B. Bioorg. Med. Chem. Lett. 2002, 12,
3407.
(12) Bayer, T. A.; Schafer, S.; Breyh, H.; Breyhan, O.; Wirths, C.;
Treiber, G. A. Clin. Neuropathol. 2006, 25, 163.
(22) (a) Reeves, D. C.; Rodriguez, S.; Lee, H.; Haddad, N.;
Krishnamurthy, D.; Senanayake, C. H. Org. Lett. 2011, 13, 2495.
(b) Munday, R. H.; Martinelli, J. R.; Buchwald, S. L. J. Am. Chem.
Soc. 2008, 130, 2754. (c) Cacchi, S.; Morera, E.; Ortar, G. Tetrahe-
dron Lett. 1985, 26, 1109.
(23) Lagerlund, O.; Mantel, M. L.; Larhed, M. Tetrahedron 2009, 65,
7646.
(24) (a) Ouyang, K.; Hao, W.; Xi, W. X.; Zhang, Z. Chem. Rev. 2015,
115, 12045. (b) Hu, J.; Zhao, Y.; Liu, J.; Zhang, Y.; Shi, Z. Angew.
Chem. Int. Ed. 2016, 55, 8718. (c) Liang, A.; Han, S.; Wang, L.; Li,
J.; Zou, D.; Wu, Y.; Wu, Y. Adv. Synth. Catal. 2015, 357, 3104.
(d) Li, W.; Wu, X.-F. Org. Lett. 2015, 17, 1910.
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