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ChemComm
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DOI: 10.1039/C6CC03414D
COMMUNICATION
Journal Name
chemistry. Further investigations of the scope, synthetic
applications and detailed computational investigations are currently
ongoing.
Generous financial support by the Department of Science and
Technology (DST), New Delhi (Grant No. SB/S1/OC-17/2013) and
the Council of Scientific and Industrial Research (CSIR), New Delhi
(Grant Nos. CSC0108 and CSC0130) is gratefully acknowledged. We
thank Dr. R. G. Gonnade, CSIR-NCL for providing single crystal X-ray
diffraction data. P. S. S. and A.C.S. thanks CSIR for the award of
Junior Research Fellowship (JRF).
3181. For related examples, see: d) I. Nakamura, T. Sato, Y.
Yamamoto, Angew. Chem., Int. Ed. 2006, 45, 4473; e) A.
Fürstner, P. W. Davies, J. Am. Chem. Soc. 2005, 127, 15024.
a) M. Taguchi, Y. Tokimizu, S. Oishi, N. Fujii, H. Ohno, Org. Lett.
2015, 17, 6250; b) Y. Tokimizu, S. Oishi, N. Fujii, H. Ohno,
Angew. Chem., Int. Ed. 2015, 54, 7862.
6
7
a) C. Wu, F. Zhao, S. Shu, J. Wang, H. Liu, RSC Adv. 2015, 5,
90396; b) F. Zhao, D. Zhang, Y. Nian, L. Zhang, W. Yang, H. Liu,
Org. Lett. 2014, 16, 5124; c) I. Nakamura, Y. Sato, S. Konta, M.
Terada, Tetrahedron Lett. 2009, 50, 2075; d) T. Shimada, I.
Nakamura, Y. Yamamoto, J. Am. Chem. Soc. 2004, 126, 10546.
For quenching of vinyl gold species with halonium ions, see: a)
S. Miaskiewicz, J-M. Weibel, P. Pale, A. Blanc, Org Lett. 2016, 18,
844; b) K. H. Nguyen, S. Tomasi, M. Le Roch, L. Toupet, J.
Renault, P. Uriac, N. J. Gouault, Org. Chem. 2013, 78, 7809; c) P.
Kothandaraman, S. R. Mothe, S. S. M. Toh, P. W. H. Chan, J. Org.
Chem. 2011, 76, 7633; d) D. Wang, X. Ye, X. Shi, Org. Lett. 2010,
12, 2088; e) L. Ye, L. Zhang, Org. Lett. 2009, 11, 3646; f) M. Yu,
G. Zhang, L. Zhang, Tetrahedron 2009, 65, 1846; g) M. Schuler,
F. Silva, C. Bobbio, A. Tessier, V. Gouverneur, Angew. Chem., Int.
Ed. 2008, 47, 7927; h) M. Yu, G. Zhang, L. Zhang, Org. Lett. 2007,
9, 2147; i) B. Crone, S. F. Kirsch, J. Org. Chem. 2007, 72, 5435; j)
A. Buzas, F. Gagosz, Org. Lett. 2006, 8, 515; k) A. Buzas, F.
Istrate, F. Gagosz, Org. Lett. 2006, 8, 1957.
Notes and reference+
8
1
Reviews: a) J. J. Vaquero and J. Alvarez-Builla, Heterocycles
Containing a Ring-Junction Nitrogen, in Modern Heterocyclic
Chemistry, ed. J. Alvarez-Builla, J. Vaquero and J. Barluenga,
Wiley-VCH, Weinheim, 2011, vol. 4, pp. 1989–2070; b) A. R.
Katritzky, C. Rees and E. F. V. Scriven, Fused Fiveand Six-
membered Rings with Ring Junction Heteroatoms, in
Comprehensive Heterocyclic Chemistry II, ed. G. Jones, Elsevier
Science, Ltd, Oxford, vol. 8, 1996. Selected reports: c) T. Fujii, Y.
Shindo, K. Hotta, D. Citterio, S. Nishiyama, K. Suzuki and K. Oka,
J. Am. Chem. Soc., 2014, 136, 2374; d) S. D. Kuduk, R. K. Chang,
C. N. Di Marco, W. J. Ray, J. Ma, M. Wittmann, M. A. Seager, K.
A. Koeplinger, C. D. Thompson, G. D. Hartman, M. T. Bilodeau,
ACS Med. Chem. Lett. 2010, 1, 263; e) Y.-S. Xu, C.-C. Zeng, Z.-G.
Jiao, L.-M. Hu, R. Zhong, Molecules 2009, 14, 868; f) M.-H. Chen,
P. Fitzgerald, S. B. Singh, E. A. O’Neill, C. D. Schwartz, C. M.
Thompson, S. J. O’Keefe, D. M. Zaller, J. B. Doherty, Bioorg.
Med. Chem. Lett. 2008, 18, 2222; g) Komatsu, N. Iwasawa, D.
Citterio, Y. Suzuki, T. Kubota, K. Tokuno, Y. Kitamura, K. Oka and
K. Suzuki, J. Am. Chem. Soc., 2004, 126, 16353; h) Q. Li, D. T. W.
Chu, A. Claiborne, C. S. Cooper, C. M. Lee, K. Raye, K. B. Berst, P.
Donner, W. Wang, L. Hasvold, A. Fung, Z. Ma, M. Tufano, R.
Flamm, L. L. Shen, J. Baranowski, A. Nilius, J. Alder, J.
Meulbroek, K. Marsh, D. Crowell, Y. Hui, L. Seif, L. M. Melcher,
R. Henry, S. Spanton, R. Faghih, L. L. Klein, S. K. Tanaka and J. J.
Plattner, J. Med. Chem., 1996, 39, 3070; i) J. R. Martin, J.-L.
Moreau, F. Jenck, Drug Dev. Res. 1995, 36, 141; j) G. M.
Eliopoulos, C. B. Wennersten, G. Cole, D. Chu, D. Pizzuti, R. C.,
Moellering, Antimicrob. Agents Chemother. 1995, 39, 850; k) K.
Kobayashi, J. Hiroi, S. Kishi, K. Sawase, Y. Hirayama, S. Chihara,
T. Imai, Y. Shigi, K. Shimomura, M. Kohsaka, Jpn J Pharmacol.
1993, 63, 73.
9
For report on Pd-catalyzed aminoalkynylation reactions under
aerobic oxidative conditions, see: (a) B. Yao, Q. Wang, J. Zhu,
Angew. Chem., Int. Ed. 2012, 51, 12311; b) A. Arcadi, S. Cacchi,
G. Fabrizi, F. Marinelli, L. M. Parisi, J. Org. Chem. 2005, 70, 6213.
10 For conceptually different report on gold-catalyzed
alkoxyalkynylation under oxidative conditions, see: M. N.
Hopkinson, J. E. Ross, G. T. Giuffredi, A. D. Gee, V. Gouverneur
Org Lett. 2010, 12, 4904.
11 Reviews: a) Y. Li, D. P. Hari, M. V. Vita, J. Waser, Angew. Chem.
Int. Ed. 2016, 55, 2; b) J. P. Brand, J. Waser, Chem. Soc. Rev.
2012, 41, 4165; For other examples, see: c) G. L. Tolnai, S.
Ganss, J. P. Brand, J. Waser, Org. Lett. 2013, 15, 112; d) Y. Li, J.
P. Brand, J. Waser, Angew. Chem., Int. Ed. 2013, 52, 6743; e) J.
P. Brand, C. Chevalley, R. Scopelliti, J. Waser, Chem. Eur. J. 2012,
18, 5655; f) J. P. Brand, C. Chevalley, J. Waser, Beilstein J. Org.
Chem. 2011, 7, 565; g) S. Nicolai, C. Piemontesi, J. Waser,
Angew. Chem., Int. Ed. 2011, 50, 4680; h) J. P. Brand, J.
Charpentier, J. Waser, Angew. Chem., Int. Ed. 2009, 48, 9346.
12 a) Y. Li, F. Xie, X. Li, J. Org. Chem. 2016, 81, 715; b) H. Wang, F.
Xie, Z. Qi, X. Li, Org. Lett. 2015, 17, 920; c) X. Zhang, Z. Qi, J. Gao,
X. Li, Org. Biomol. Chem. 2014, 12, 9329; d) F. Xie, Z. Qi, S. Yu, X.
Li, J. Am. Chem. Soc. 2014, 136, 4780.
13 a) C. Feng, D. Feng, Y. Luo, T.-P. Loh, Org. Lett. 2014, 16, 5956;
b) C. Feng, D. Feng, T.-P. Loh, Chem. Commun. 2014, 50, 9865;
c) C. Feng, T.-P. Loh, Angew. Chem., Int. Ed. 2014, 53, 2722.
14 K. Collins, F. Lied, F. Glorius, Chem. Commun. 2014, 50, 4459.
15 S. T. Staben, J. J. Kennedy-Smith, D. Huang, B. K. Corkey, R. L.
LaLonde, F. D. Toste, Angew. Chem. Int. Ed. 2006, 45, 5991.
16 See supporting information for details.
2
3
Selected reports on catalytic approaches to quinolizinones: a) A.
Rosas-Sánchez, R. A. Toscano, J. G. López-Cortés and M. C.
Ortega-Alfaro, Dalton Trans., 2015, 44, 578; b) H. Yu, G. Zhang,
H. Huang, Angew. Chem., Int. Ed. 2015, 54, 10912; c) T. A.
Alanine, W. R. J. D. Galloway, T. M. McGuire, D. R. Spring, Eur. J.
Org. Chem. 2014, 5767.
General reviews: a) K. Ouyang, W. Hao, W.-X. Zhang, Z. Xi,
Chem. Rev. 2015, 115, 12045; b) D. Bouyssi, N. Monteiro, G.
Balme, Beilstein J. Org. Chem. 2011, 7, 1387; c) N. T. Patil, R. D.
Kavthe, Y. Yamamoto, Adv. Heterocycl. Chem. 2010, 101, 75; d)
J. Barluenga, F. Rodríguez, F. J. Fañanás, Chem.-Asian J. 2009, 4,
1036; e) K. Krüger, A. Tillack, M. Beller, Adv. Synth. Catal. 2008,
350, 2153; f) G. Battistuzzi, S. Cacchi, G. Fabrizi, Eur. J. Org.
Chem. 2002, 16, 2671.
17 A. C. Shaikh, D. R. Shinde, N. T. Patil, Org. Lett. 2016, 18, 1056.
18 N. T. Patil, V. S. Shinde; B. Gajula, Org. Biomol. Chem. 2012, 10,
211.
4
5
a) X. Zeng, R. Kinjo, B. Donnadieu, G. Bertrand, Angew. Chem.,
Int. Ed. 2010, 49, 942. For related example, see: b) I. Nakamura,
Y. Mizushima, U. Yamagishi, Y. Yamamoto, Tetrahedron 2007,
63, 8670.
a) V. Gobé, P. Retailleua, X. Guinchard, Chem.-Eur. J. 2015, 21,
17587; b) K. C. Majumdar, S. Hazra, B. Roy, Tetrahedron Lett.
2011, 52, 6697; c) F. M. Istrate, F. Gagosz, Org. Lett. 2007, 9,
4 | J. Name., 2012, 00, 1-3
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