Organic Letters
Letter
(5) Clements-Jewery, S.; Danswan, G.; Gardner, C. R.; Matharu, S. S.;
Murdoch, R.; Tully, W. R.; Westwood, R. J. Med. Chem. 1988, 31, 1220.
(6) Chao, Q.; Sprankle, K. G.; Grotzfeld, K. M.; Lai, A. G.; Carter, T. A.;
Velasco, A. M.; Gunawardane, R. N.; Cramer, M. D.; Gardner, M. F.;
James, J.; Zarrinkar, P. P.; Patel, H. K.; Bhagwat, S. S. J. Med. Chem. 2009,
52, 7808.
(7) (a) Bakherad, M.; Nasr-Isfahani, H.; Keivanloo, A.; Sang, G.
Tetrahedron Lett. 2008, 49, 6188. (b) Wu, Z.; Huang, Q.; Zhou, X.; Yu,
L.; Li, Z.; Wu, D. Eur. J. Org. Chem. 2011, 2011, 5242. (c) Christodoulou,
M. S.; Colombo, F.; Passarella, D.; Ieronimo, G.; Zuco, V.; De Cesare,
M.; Zunino, F. Bioorg. Med. Chem. 2011, 19, 1649. (d) Zhang, X.; Jia, J.;
Ma, C. Org. Biomol. Chem. 2012, 10, 7944. (e) Guchhait, S. K.;
Chaudhary, V. Org. Biomol. Chem. 2014, 12, 6694. (f) Mishra, S.; Monir,
K.; Mitra, S.; Hajra, A. Org. Lett. 2014, 16, 6084. (g) Mir, N. A.; Shah, T.
A.; Ahmed, S.; Muneer, M.; Rath, N. P.; Ahmad, M. Tetrahedron Lett.
2014, 55, 1706.
ditions. The tandem ring-closing/opening/recyclization rear-
rangement involving C−S bond cleavage and formation of three
new bonds (C−C, C−N, C−S) provides convenient access to
benzo[d]imidazo[2,1-b]thiazoles when the C2 position of
benzothiazole is linked to a C−H or C−C bond. When 2-chloro-
or 2-bromobenzothiazoles are used under the same reaction
conditions, the isomeric benzo[d]imidazo[5,1-b]thiazoles are
formed selectively. The reactions were carried out at room
temperature with moderate to excellent yields, and a wide range
of functional groups are tolerated.
ASSOCIATED CONTENT
* Supporting Information
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S
The Supporting Information is available free of charge on the
(8) (a) Schollkopf, U. Angew. Chem., Int. Ed. Engl. 1977, 16, 339.
̈
(b) Zhu, J. Eur. J. Org. Chem. 2003, 2003, 1133. (c) Ramon
́
, D. J.; Yus, M.
General experimental procedure, characterization data of
the compounds (PDF) and X-ray crystallographic data for
Angew. Chem., Int. Ed. 2005, 44, 1602. (d) Domling, A. Chem. Rev. 2006,
̈
106, 17. (e) Gulevich, A. V.; Zhdanko, A. G.; Orru, R. V. A.; Nenajdenko,
V. G. Chem. Rev. 2010, 110, 5235. (f) Lygin, A. V.; De Meijere, A. Angew.
Chem., Int. Ed. 2010, 49, 9094. (g) Qiu, G.; Ding, Q.; Wu, J. Chem. Soc.
Rev. 2013, 42, 5257. (h) Chakrabarty, S.; Choudhary, S.; Doshi, A.; Liu,
F.-Q.; Mohan, R.; Ravindra, M. P.; Shah, D.; Yang, X.; Fleming, F. F. Adv.
Synth. Catal. 2014, 356, 2135.
AUTHOR INFORMATION
Corresponding Author
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(9) For selected examples, see: (a) Xue, M.-X.; Guo, C.; Gong, L.-Z.
Synlett 2009, 2009, 2191. (b) Sladojevich, F.; Trabocchi, A.; Guarna, A.;
Dixon, D. J. J. Am. Chem. Soc. 2011, 133, 1710. (c) Kim, H. Y.; Oh, K. Org.
Lett. 2011, 13, 1306. (d) Zhao, M.-X.; Zhou, H.; Tang, W.-H.; Qu, W.-S.;
Shi, M. Adv. Synth. Catal. 2013, 355, 1277. (e) de la Campa, R.; Ortín, I.;
Dixon, D. J. Angew. Chem., Int. Ed. 2015, 54, 4895.
(10) For selected examples, see: (a) Scheffelaar, R.; Paravidino, M.;
Muilwijk, D.; Lutz, M.; Spek, A. L.; De Kanter, F. J. J.; Orru, R. V. A.;
Ruijter, E. Org. Lett. 2009, 11, 125. (b) Zhang, Z.-W.; Lu, G.; Chen, M.-
M.; Lin, N.; Li, Y.-B.; Hayashi, T.; Chan, A. S. C. Tetrahedron: Asymmetry
2010, 21, 1715. (c) Nakamura, S.; Maeno, Y.; Ohara, M.; Yamamura, A.;
Funahashi, Y.; Shibata, N. Org. Lett. 2012, 14, 2960. (d) Lalli, C.; Bouma,
M. J.; Bonne, D.; Masson, G.; Zhu, J. Chem. - Eur. J. 2011, 17, 880.
(e) Zhao, M.-X.; Bi, H.-L.; Jiang, R. H.; Xu, X. W.; Shi, M. Org. Lett. 2014,
16, 4566. (f) Shao, P.-L.;Liao, J.-Y.; Ho, Y.-A.; Zhao, Y. Angew. Chem., Int.
Ed. 2014, 53, 5435. (g) Hayashi, M.; Iwanaga, M.; Shiomi, N.; Nakane,
D.; Masuda, H.; Nakamura, S. Angew. Chem., Int. Ed. 2014, 53, 8411.
(11) For selected examples, see: (a) Guo, C.; Xue, M.-X.; Zhu, M.-K.;
Gong, L.-Z. Angew. Chem., Int. Ed. 2008, 47, 3414. (b) Song, J.; Guo, C.;
Chen, P.-H.; Yu, J.; Luo, S.-W.; Gong, L.-Z. Chem. - Eur. J. 2011, 17, 7786.
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
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This work was supported by National Science Foundation of
China (21272233, 21472190).
REFERENCES
■
(1) (a) Dupont, J.; de Souza, R. F.; Suarez, P. A. Z. Chem. Rev. 2002,
102, 3667. (b) Bellina, F.; Cauteruccio, S.; Rossi, R. Tetrahedron 2007,
63, 4571. (c) Lombardino, J. G.; Wiseman, E. H. J. Med. Chem. 1974, 17,
1182. (d) Corell, T.; Hasselmann, G. Acta Pharmacol. Toxicol. 1983, 53,
288.
(2) (a) Messina, F.; Botta, M.; Corelli, F.; Paladino, A. Tetrahedron:
Asymmetry 2000, 11, 4895. (b) Abdel-Wahab, B. F.; Abdel-Aziz, H. A.;
Ahmed, E. M. Eur. J. Med. Chem. 2009, 44, 2632. (c) Kaniwa, K.; Ohtsuki,
T.; Yamamoto, Y.; Ishibashi, M. Tetrahedron Lett. 2006, 47, 1505. (d) Di
Nunno, L.; Franchini, C.; Scilimati, A.; Sinicropi, M. S.; Tortorella, P.
Tetrahedron: Asymmetry 2000, 11, 1571.
́ ́
(c) Arroniz, C.; Gil-Gonzalez, A.; Semak, V.; Escolano, C.; Bosch, J.;
Amat, M. Eur. J. Org. Chem. 2011, 2011, 3755. (d) Padilla, S.; Adrio, J.;
Carretero, J. C. J. Org. Chem. 2012, 77, 4161. (e) Zhao, M.-X.; Wei, D.-K.;
Ji, F.-H.; Zhao, X.-L.; Shi, M. Chem. - Asian J. 2012, 7, 2777. (f) Wang, L.-
L.; Bai, J.-F.; Peng, L.; Qi, L.-W.; Jia, L.-N.; Guo, Y.-L.; Luo, X.-Y.; Xu, X.-
Y.; Wang, L.-X. Chem. Commun. 2012, 48, 5175.
(3) For selected examples of bioactive compounds containing A:
(a) Farag, A. M.; Mayhoub, A. S.; Barakat, S. E.; Bayomi, A. H. Bioorg.
Med. Chem. 2008, 16, 4569. (b) Andreani, A.; Burnelli, S.; Granaiola, M.;
Leoni, A. J. Med. Chem. 2008, 51, 809. (c) Andreani, A.; Burnelli, S.;
Granaiola, M.; Leoni, A. J. Med. Chem. 2008, 51, 7508. (d) Palkar, M.;
Noolvi, M.; Sankangoud, R.; Maddi, V. Arch. Pharm. 2010, 343, 353.
(e) Al-Tel, T. H.; Al-Qawasmeh, R. A.; Zaarour, R. Eur. J. Med. Chem.
2011, 46, 1874. (f) Furlan, A.; Colombo, F.; Kover, A.; Issaly, N. Eur. J.
Med. Chem. 2012, 47, 239. (g) Andreani, A.; Granaiola, M.; Locatelli, A.;
Morigi, R. J. Med. Chem. 2012, 55, 2078. (h) Blackburn, C.; Duffey, M.
O.; Gould, A. E.; Kulkarni, B. Bioorg. Med. Chem. Lett. 2010, 20, 4795.
(i) Yousefi, B. H.; Manook, A.; Drzezga, A.; Reutern, B. J. Med. Chem.
2011, 54, 949. (j) Andreani, A.; Granaiola, M.; Leoni, A.; Locatelli, A.;
Morigi, R. Eur. J. Med. Chem. 2011, 46, 4311. (k) Yousefi, B. H.; Drzezga,
A.; Reutern, B.; Manook, A. ACS Med. Chem. Lett. 2011, 2, 673.
(l) Alagille, D.; DaCosta, H.; Baldwin, R. M.; Tamagnan, G. D. Bioorg.
Med. Chem. Lett. 2011, 21, 2966.
(12) Liao, J.-Y.; Shao, P.-L.; Zhao, Y. J. Am. Chem. Soc. 2015, 137, 628.
(13) (a) Kamijo, S.; Kanazawa, C.; Yamamoto, Y. J. Am. Chem. Soc.
2005, 127, 9260. (b) Liu, J.; Fang, Z.; Zhang, Q.; Liu, Q.; Bi, X. Angew.
Chem., Int. Ed. 2013, 52, 6953. (c) Gao, M.; He, C.; Chen, H.; Bai, R.;
Cheng, B.; Lei, A. Angew. Chem., Int. Ed. 2013, 52, 6958.
(14) (a) Kanazawa, C.; Kamijo, S.; Yamamoto, Y. J. Am. Chem. Soc.
2006, 128, 10662. (b) Grigg, R.; Lansdell, M. I.; Thornton-Pett, M.
Tetrahedron 1999, 55, 2025. (c) Pooi, B.; Lee, J.; Choi, K.; Hirao, H.;
Hong, S. H. J. Org. Chem. 2014, 79, 9231.
(15) Du, J.; Xu, X.; Li, Y.; Pan, L.; Liu, Q. Org. Lett. 2014, 16, 4004.
(16) Buyck, T.; Wang, Q.; Zhu, J. J. Am. Chem. Soc. 2014, 136, 11524.
(17) He, Z.-L.; Wang, C.-J. Chem. Commun. 2015, 51, 534.
(18) Li, Y.; Xu, X.; Tan, J.; Xia, C.; Zhang, D.; Liu, Q. J. Am. Chem. Soc.
2011, 133, 1775.
(4) For examples of bioactive compounds containing B, see: Banerjee,
A.; Narayana, L.; Raje, F. A.; Pisal, D. V.; Kadam, P. A.; Gullapalli, S.;
Kumar, H.; More, S. V.; Bajpai, M.; Sangana, R. R.; Jadhav, S.; Gudi, G. S.;
Khairatkar-Joshi, N.; Merugu, R. R. T.; Voleti, S. R.; Gharat, L. A. Bioorg.
Med. Chem. Lett. 2013, 23, 6747.
(19) Tan, J.; Xu, X.; Zhang, L.; Li, Y.; Liu, Q. Angew. Chem., Int. Ed.
2009, 48, 2868.
(20) Xu, X.; Zhang, L.; Liu, X.; Pan, L.; Liu, Q. Angew. Chem., Int. Ed.
2013, 52, 9271.
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