Please do not adjust margins
RSC Advances
Page 5 of 5
DOI: 10.1039/C5RA11159E
Journal Name
ARTICLE
δ 11.16 (s, br, 1H), 7.70 ꢀ 7.65 (m, 1H), 7.45 (d, 1H, J = 8 Hz), 7.11 13 Y. Deng, R. Xu and Y. Ye, J. Chin. Pharm. Sci., 2000, 9,
ꢀ 7.07 (m, 1H ), 2.25 (s, 3H) ppm; 13C NMR (CDCl3, 100 MHz) δ
162.6, 159.7, 159.4 154.2, 151.3, 135.3, 122.9, 113.1, 112.9, 22.0
ppm; GCMS (EI, 70 eV): m/z (%): 178 (100, M+), 163 (19), 110
(23), 108 (21), 42 (29).
116.
14 Z. Z. Ma, Y. Hano, T. Nomura and Y. J. Chen, Heterocycles
1997, 46, 541.
15 (a) P. Griess, Ber. Deutsch. Chem. Ges., 1869, 2, 415; (b) P.
,
Griess, Ber. Deutsch. Chem. Ges., 1878, 11, 1985.
16 S. von Niementowski, J. Prakt. Chem., 1895, 51, 564.
17 Y. Kabri, A. Gellis and P. Vanelle, Green Chem., 2009, 11,
5-Fluoro-2-cyclopropylquinazolin-4(3H)-one (3j). PE : EA (1 :
201.
1).White solid. Yield 78% (2ꢀiodobenzoic acid as the substrate);
18 (
Commun., 2008, 6333; (b) X. Liu, H. Fu, Y. Jiang, and Y.
Zhao, Angew. Chem. Int. Ed., 2009, 48, 348; ( ) X. Huang, H.
Yang, H. Fu, R. Qiao and Y. Zhao, Synthesis, 2009, 16, 2679;
) W. He, H. Zhao, R. Yao and M. Cai, RSC Adv., 2014, 4,
a) C. Huang, Y. Fu, H. Fu, Y. Jiang and Y. Zhao, Chem.
1
55% (2ꢀbromobenzoic acid as the substrate). H NMR (CDCl3, 400
MHz) δ 10.51 (s, br, 1H), 7.64 ꢀ 7.58 (m, 1H), 7.36 (d, 1H, J = 4
Hz), 7.03 ꢀ 6.99 (m, 1H), 1.85 ꢀ 1.81 (m, 1H), 1.28 ꢀ 1.23 (m, 2H),
1.13 (m, 2H) ppm; 13C NMR (CDCl3, 100 MHz), δ 162.1, 161.1,
160, 154.2, 151.8, 135, 122.9, 112.9, 112, 14.5, 10 ppm; GCMS (EI,
70 eV): m/z (%): 203 (1000, M+), 204 (65), 137 (20), 110 (14), 108
(16), 40 (39). HRMS (ESIꢀion trap) m/z calcd [(M+H)+] 205.0777,
found 205.0767.
c
(
d
50285; (e) M. U. Hung, B. S. Liao, Y. H. Liu, S. M. Peng and
S. T. Liu, Appl. Organometal. Chem., 2014, 28, 661.
19 (a) L. Yu, M. Wang, P. Li and L. Wang, Appl. Organometal.
Chem., 2012, 26, 576; (b) X. Zhang, D. Ye, H. Sun, D. Guo,
J. Wang, H. Huang, X. Zhang, H. Jiang and H. Liu, Green
Chem., 2009, 11, 1881.
20 (
Bonnamour, E. Zuidema, S. Chang and C. Bolm, Adv. Synth.
Catal., 2010, 352, 2892; ( ) R. Cano, D. J. Ramón and M.
Yus, J. Org. Chem., 2011, 76, 654; ( ) Y. Fang, Y. Zheng and
Z. Wang, Eur. J. Org. Chem., 2012, 1495; ( ) L. H. Zou, J.
Reball, J. Mottweiler, and C. Bolm, Chem. Commun., 2012,
48, 11307; ( ) F. Diness and D. P. Fairlie, Angew. Chem., Int.
Ed., 2012, 51, 8012; ( ) M. Carmen PérezꢀAguilar, and
Valdés, C. Angew. Chem., Int. Ed., 2012, 51, 5953; ( ) N.
Jalalian, T. B. Petersen, and B. Olofsson, Chem. Eur. J.,
2012, 14140; ( ) K. C. Majumdar, S. Ganai, Nandi, R. K. and
Ray, K., Tetrahedron Lett., 2012, 53, 1553.
21 ( ) Y. Yuan, I. Thomé, S. H. Kim, D. Chen, A. Beyer; J.
Bonnamour, E. Zuidema, S. Chang and C. Bolm, Adv. Synth.
Catal., 2010, 352, 2892; ( ) R. Cano, D. J. Ramón and Yus,
M., J. Org. Chem., 2011, 76, 654; ( ) Y. Fang, Y. Zheng and
Z. Wang, Eur. J. Org. Chem., 2012, 1495; ( ) L. H. Zou, J.
Reball, J. Mottweiler and C. Bolm, Chem. Commun., 2012,
48, 11307; ( ) F. Diness and D. P. Fairlie, Angew. Chem. Int.
Ed., 2012, 51, 8012; ( ) M. Carmen Pérez Aguilar, and C.
Valdés, Angew. Chem., Int. Ed., 2012, 51, 5953; ( ) N.
Jalalian, T. B. Petersen, and B. Olofsson, Chem. Eur. J.,
2012, 14140; ( ) I. Thom, C. Besson, T. Kleine and C. Bolm,
Angew. Chem. Int. Ed., 2013, 52, 1; ( ) S. K. Xiang, W. Tan,
a) Y. Yuan, I. Thomé, S. H. Kim, D. Chen, A. Beyer, J.
Acknowledgements
b
c
The author (Abhishek R. Tiwari) is greatly thankful to
University Grant Commission (UGC), New Delhi, India for
providing UGCꢀBSR Fellowship.
d
e
f
g
Notes and references
h
1
(a
) A. Witt and J. Bergman, Curr. Org. Chem., 2003, 7, 659,
and references cited therein; ( ) S. B. Mhaske, N. P. Argade,
Tetrahedron, 2006, 62, 9787, and references cited therein;(c)
G. Capuano, Gazzetta Chimica Italiana, 1956, 86, 119.
b
a
b
2
(
a
) D. J. Connolly, D. Cusack, T. P. O. Sullivan and P. J.
c
Guiry, Tetrahedron, 2005, 61, 10153; ( ) Z. Ma, Y. Hano and
b
d
T. Nomura, Heterocycles, 2005, 65, 2203.
3
4
5
A. Nathubhai, P. J. Wood, M. D. Lloyd, A. S. Thompson and
M. D. Threadgill, ACS Med. Chem. Lett., 2013, 4, 1173.
J. Tani, Y. Yamada, T. Oine, T. Ochiai, R. Ishida and I.
Inoue, J. Med. Chem., 1979, 22, 95.
V. Alagarsamy, K. Dhanabal, , P. Parthiban, G. Anjana, G.
Deepa, B. Murugesan, S. Rajkumar, and A. J. Beevi, J.
Pharm. Pharmacol., 2007, 59, 669.
e
f
g
h
i
D. X. Zhang, X. L. Tian, C. Feng, B. Q. Wang, K. Q. Zhao,
P. Hu and H. Yang, Org. Biomol. Chem., 2013, 11, 7271.
22 R. Huisgen and J. Sauer, Angew. Chem., 1960, 72, 91.
6
7
8
(
a
) H. J. Hess, T. H. Cronin and A. Scriabine, J. Med. Chem.,
1968, 11, 130; ( ) M. A. Hussain, A. T. Chiu, W. A. Price, P.
b
B. Timmermans and E. Shefter, Pharm. Res., 1988, 5, 242.
P. A. Ple,. T. P. Green, L. F. Hennequin, J. Curwen, M.
Fennell, J. Allen, C. Lambertvan der Brempt and G. Costello,
J. Med. Chem., 2004, 47, 871.
23 (
Lett., 2008, 10, 4673; (
Org. Lett., 2012, 14, 3948; (c) D. S. Roman, Y. Takahashi
and A. B. Charette, Org. Lett., 2011, 13, 3242; ( ) W. Liu, H.
a
) S. Yanagisawa, K. Ueda, T. Taniguchi and K. Itami, Org.
b
) A. Beyer, J. Buendia, and C. Bolm,
d
(a
) K. Waisser, J. Gregor, H. Dostal, J. Kunes, L. Kubicova,
Cao, H. Zhang, K. H. Chung, C. He, H. Wang, F. Y. Kwong
and A. Lei, J. Am. Chem. Soc., 2010, 132, 16737.
24 A. Ilangovan and G. Satish, J. Org. Chem. 2014, 79, 4984.
25 For a review, see: J. F. Bunnett and R. E. Zahler, Chem. Rev.,
1951, 49, 273.
V. Klimesova, and J. Kaustova, Farmaco, 2001, 56, 803; (
b
)
J. Kunes, J. Bazant, M. Pour, K. Waisser, M. Slosarek and J.
Janota, Farmaco, 2000, 55, 725.
9
(a
) T. C. Chien, C. S. Chen, F. H. Yu and J. W. Chern, Chem.
Pharm. Bull., 2004, 52, 1422; ( ) T. Herget, M. Freitag, M.
b
Morbitzer, R. Kupfer, T. Stamminger, and M. Marschall,
Antimicrob. Agents Chemother., 2004, 48, 4154.
10 (
a
b
) L. A. Doyle, and D. D. Ross, Oncogene, 2003, 22, 7340;
) E. A. Henderson, V. Bavetsias, D. S. Theti, S. C. Wilson.
(
R. Clauss and A. L. Jackman, Bioorg. Med. Chem., 2006, 14,
5020.
11 C. Wattanapiromsakul, P. I. Forster and P. G. Waterman,
Phytochemistry, 2003, 64, 609.
12 S. Yoshida, T. Aoyagi, S. Harada, N. Matsuda, T. Ikeda, H.
Naganawa, M. Hamada, and T. Takeuchi, J. Antibiot., 1991,
44, 111.
This journal is © The Royal Society of Chemistry 20xx
J. Name., 2013, 00, 1-3 | 5
Please do not adjust margins