ANNAREDDYGARI ET AL.
9
G. Biagi, I. Giorgi, O. Livi, C. Manera, V. Scartoni, A.
Lucacchini, G. Giannaccini, P. L. Barili, Eur. J. Med. Chem.
2000, 35, 333.
4.1.29 | 2‐Bromopyrido[3′,2′:4,5]
imidazo[1,2‐a]quinazoline (4g)
Pale yellow solid; m.p.: above 230°C; 1H NMR (400 MHz,
DMSO‐d6) δ 9.12 (s, 1H), 9.04 (d, J = 2.8 Hz, 1H), 8.59 (t, J
= 4.1 Hz, 1H), 8.25 (m, 1H), 8.00 (dd, J = 8.5, 5.1 Hz, 1H),
7.96 (d, J = 4.7 Hz, 1H), 7.55 (dd, J = 8.0, 4.8 Hz, 1H). 13C
NMR (100 MHz, DMSO‐d6) δ 164.2, 159.1, 142.6, 138.5,
138.1, 135.6, 131.6, 126.8, 122.7, 120.3, 115.4, 115.0,
114.1. HRMS (ESI): m/z Calcd. for C13H8BrN4 [M +
H]+ : 298.9927; found: 298.9932.
[4] H. Xu, L.‐I. Fan, Eur. J. Med. Chem. 2011, 46, 1919.
[5] J. Guillon, S. Moreau, E. Mouray, V. Sinou, I. Forfar, S. B.
Fabre, V. Desplat, P. Millet, D. Parzy, C. Jerry, P. Grellier,
Bioorg. Med. Chem. 2008, 16, 9133.
[6] S. Taliani, I. Pugliesi, E. Barresi, S. Salerno, C. Marchand, K.
Agama, F. Simorini, C. L. Motta, A. N. Marini, F. S. D. Leva,
L. Marinelli, S. Cosconati, F. Novellino, Y. Pommier, R. D.
Santo, F. D. Settimo, J. Med. Chem. 2013, 56, 7458.
[7] a) L. Wang, W. Guo, X.‐X. Zhang, X.‐D. Xia, Org. Lett. 2012, 14,
740; b) S. Samala, R. K. Arigela, R. Kant, B. Kundu, J. Org.
Chem. 2014, 79, 2491.
4.1.30 | 5H‐Benzo[4,5]thiazolo[3,2‐a]
quinazoline (5a)
[8] a) J. T. Reeves, D. R. Fandrick, Z. Tan, J. J. Song, H. Lee, N. K.
Yee, C. H. Senanayake, J. Org. Chem. 2010, 75, 992; b) A.
Huang, F. Liu, C. Zhan, Y. Liu, Ma. C. Org. Biomol. Chem.
2011, 9, 7351.
1
Yellow solid; m.p.: 131°C to 133°C; H NMR (400 MHz,
CDCl3) δ 7.57 (t, J = 7.9 Hz, 2H), 7.46 (t, J = 7.7 Hz,
1H), 7.30 (t, J = 7.5 Hz, 2H), 7.15 – 7.07 (m, 3H), 4.71
(s, 2H). 13C NMR (125 MHz, CDCl3) δ 167.5, 161.9,
160.0, 152.0, 129.7, 129.6, 126.0, 124.4, 121.7, 120.8,
118.8, 115.6, 115.4, 43.2. HRMS (ESI): m/z Calcd. for
C14H11N2S [M + H]+ : 239.0638; found: 239.0642.
[9] a) J.‐y. Kato, H. Aoyama, T. Yokomatsu, Org. Biomol. Chem.
2013, 11, 1171; b) L. Gao, Y. Song, X. Zhang, S. Guo, X. Fan,
Tetrahedron. Lett. 2014, 55, 4997.
[10] A. V. Ivachtchenko, E. S. Golovina, M. G. Kadieva, A. G.
Koryakova, S. M. Kovalenko, O. D. Mitkin, I. M. Okun, I. M.
Ravnyeyko, S. E. Tkachenko, O. V. Zaremba, J. Comb. Chem.
2010, 12, 445.
[11] M. A. Povalyakhina, A. S. Antonov, O. V. Dyablo, V. A.
ACKNOWLEDGMENTS
Ozeryanskii, A. F. Pozharskii, J. Org. Chem. 2011, 76, 7157.
Srikanth Annareddygari thanks Dr. Jcr, Biosciences Pri-
vate Limited, Hyderabad for facilities and analytical
support.
[12] a) S. Xu, J. Lu, H. Fu, Chem. Commun. 2011, 47, 5596; b) C. Li,
W. T. Zhang, X.‐S. Wang, J. Org. Chem. 2014, 79, 5847.
[13] For selected reviews on metal‐catalyzed N‐arylation see: a) I. P.
Beletskaya, A. V. Cheprakov, Organometallics 2012, 31, 7753; b)
J. Bariwal, E. Van der Eycken, Chem. Soc. Rev. 2013, 42, 9283; c)
M.‐L. Louillat, F. W. Patureau, Chem. Soc. Rev. 2014, 43, 901; d)
T. R. M. Rauws, B. U. W. Maes, Chem. Soc. Rev. 2012, 41, 2463.
ORCID
Srikanth Annareddygari
[14] Pd‐catalyzed intramolecular N‐arylation see a) X. Luo, E.
Chenard, P. Martens, Y.‐X. Cheng, M. J. Tomaszewski, Org.
Lett. 2010, 12, 3574; b) C. T. Brain, S. A. Brunton, Tetrahedron
Lett. 2002, 43, 1893; c) C. T. Brain, J. T. Steer, J. Org. Chem.
2003, 68, 6814; d) G. Evindar, R. A. Batey, Org. Lett. 2003, 5,
133; e) Y. Qing Fang, M. Lautens, Org. Lett. 2005, 7, 3549; f)
A. Fayol, Q. Fang, M. Lautens, Org. Lett. 2006, 8, 4203.
NOTES AND REFERENCE
[1] a) M. Ishikura, T. Abe, T. Choshi, S. Hibino, Nat. Prod. Rep.
2013, 30, 694; b) B. R. Hili, A. K. Yudin, Nat. Chem. Biol.
2006, 2, 284; c) S. Agarwal, Nature Rev. Drug Disov. 2010, 9,
427; d) G. Yanlong, H. Wenbo, C. Shaomin, W. Xin, Org. Lett.
2018, 20, 4285; e) H. Wenbo, C. Shaomin, C. Zhiyan, Y. Meie,
L. Minghao, G. Yanlong, J. Org. Chem. 2019, 84, 5655.
[15] Cu‐catalyzed intramolecular N‐arylation see a)W. Yang, Y.
Long, S. Zhang, Y. Zeng, Q. Cai, Org. Lett. 2013, 15, 3598; b)
Z. Sun, H. Li, H. Jiang, H. Liu, Org. Lett. 2008, 10, 3263; c) S.
Murru, B. K. Patel, J. L. Bras, J. Muzart, J. Org. Chem. 2009,
74, 2217; d) J. Peng, M. Ye, C. Zong, F. Hu, L. Feng, X. Wang,
Y. Wang, C. Chen, J. Org. Chem. 2011, 76, 716; e) K. Hirano, A.
T. Biju, F. J. Glorius, Org. Chem. 2009, 74, 9570; f) P. Saha, T.
Ramana, N. Purkait, A. Ali, R. Paul, T. Punniyamurthy,
J. Org. Chem. 2009, 74, 8719; g) S. E. Kiruthika, P. T. Perumal,
Org. Lett. 2014, 16, 484.
[2] a) M. Anzini, A. Cappelli, S. Vomero, G. Giorgi, T. Langer, G.
Bruni, R. Romeo, A. S. Basile, J. Med. Chem. 1996, 39, 4275;
b) G. A. Herman, A. Bergman, F. Liu, C. Stevens, A. Q. Wang,
W. Zeng, L. Chen, K. Snyder, D. Hilliard, M. Tanen, W. A.
Tanaka, A. G. Meehan, K. Lasseter, S. Dilzer, R. Blum, J. A.
Wagner, J. Clin. Pharmacol. 2006, 46, 876.
[3] a) L. Ronga, M. D. Favero, A. Cohen, C. Soum, P. L. Pape, S.
Savrimoutou, N. Pinaud, C. Mullie, S. Daulouede, P.
Vincendeau, N. Farvacques, P. Agnamey, F. Pagniez, S. Hutter,
N. Azas, P. Sonnet, J. Guillon, Eur. J. Med. Chem. 2014, 81, 378;
b) C. J. Wenthur, R. D. Morrison, J. S. Daniel, P. J. Conn, C. W.
Lindsley, Bioorg. Med. Chem. Lett. 2014, 24, 2693; c) L. Bertelli,
[16] For selected examples of metal‐free intramolecular N‐arylation,
see: a) A. Beyer, C. M. M. Reucher, C. Bolm, Org. Lett. 2011, 13,
2876; b) I. Thome, C. Bolm, Org. Lett. 2012, 14, 1892; c) M. T.
Barros, S. S. Dey, C. D. Maycock, P. Rodrigues, Chem. Commun.
2012, 48, 10901; d) W.‐B. Wu, J.‐M. Huang, Org. Lett. 2012, 14,
5832; e) X. Zhang, L. Wang, Green Chem. 2012, 14, 2141; f) Y.