Collect. Czech. Chem. Commun. 2009, 74, 957-972
https://doi.org/10.1135/cccc2009014
Published online 2009-06-18 10:32:42

Facile and efficient synthesis of indazole derivatives by 1,3-cycloaddition of arynes with diazo compounds and azomethine imides

Tienan Jin*, Fan Yang and Yoshinori Yamamoto*

Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan

References

1a. Wrobleski S. T., Chen P., Hynes J., Jr., Lin S., Norris D. J., Pandit C. R., Spergel S., Wu H., Tokarski J. S., Chen X., Gilloly K. M., Kiener P. A., McIntyre K. W., Patil-Koota V., Shuster D. J., Turk L. A., Yang G., Leftheris K.: J. Med. Chem. 2003, 46, 2110. <https://doi.org/10.1021/jm020329q>
1b. Bermudez J., Fake C. S., Joiner G. F., Joiner K. A., King F. D., Miner W. D., Sanger G. J.: J. Med. Chem. 1997, 33, 1924. <https://doi.org/10.1021/jm00169a016>
1c. Boehm H.-J., Boehringer M., Bur D., Gmuender H., Huber W., Klaus W., Kostrwa D., Kuehne H., Luebbers T., Meunier-Keller N., Mueller F.: J. Med. Chem. 2000, 43, 2664. <https://doi.org/10.1021/jm000017s>
1d. Corsi G., Palazzo G., Germani C., Barcellona P. S., Silvestrini B.: J. Med. Chem. 1976, 19, 778. <https://doi.org/10.1021/jm00228a008>
1e. Bistochi G. A., De Meo G., Pedini M., Ricci A., Brouilhet H., Bucherie S., Rabaud M., Jacquignon P.: Farmaco Ed. Sci. 1981, 36, 315.
2a. Stadlbauer W.: Sci. Synthesis 2002, 12, 227.
2b. Jacobson P., Huber L.: Ber. Dtsch. Chem. Ges. 1908, 41, 660. <https://doi.org/10.1002/cber.190804101127>
2c. Rüchardt C., Hassmann V.: Liebigs Ann. Chem. 1980, 908. <https://doi.org/10.1002/jlac.198019800611>
2d. Yoshida T., Matsuura N., Yamamoto K., Doi M., Shimada K., Morie T., Kato S.: Heterocycles 1996, 43, 2701. <https://doi.org/10.3987/COM-96-7614>
2e. Caron S., Vazquez E.: Synthesis 1999, 588. <https://doi.org/10.1055/s-1999-3431>
2f. Jukin K., Hsu M. C., Fernando D., Leanna M. R.: J. Org. Chem. 2006, 71, 8166.
2g. Elguero J. in: Comprehensive Heterocyclic Chemistry (A. R. Katrizky and C. W. Rees, Eds), Vol. 5, pp. 167–303. Pergamon, New York 1984.
3a. Baum G., Bernard R., Shechter H.: J. Am. Chem. Soc. 1967, 89, 5307. <https://doi.org/10.1021/ja00996a052>
3b. Baum G., Shechter H.: J. Org. Chem. 1976, 41, 2120. <https://doi.org/10.1021/jo00874a011>
3c. Yamazaki T., Shechter H.: Tetrahedron Lett. 1972, 13, 4533. <https://doi.org/10.1016/S0040-4039(01)94360-6>
3d. Yamazaki T., Shechter H.: Tetrahedron Lett. 1973, 14, 1417. <https://doi.org/10.1016/S0040-4039(01)95958-1>
3e. Yamazaki T., Baum G., Shechter H.: Tetrahedron Lett. 1974, 15, 4421. <https://doi.org/10.1016/S0040-4039(01)92179-3>
4a. Huisgen R., Knorr R.: Naturwissenschaften 1961, 48, 716. <https://doi.org/10.1007/BF00620961>
4b. Taylor E. C., Sobieray D. M.: Tetrahedron 1991, 47, 9599. <https://doi.org/10.1016/S0040-4020(01)91027-0>
5. Himeshima Y., Sonoda T., Kobayashi H.: Chem. Lett. 1983, 1211. <https://doi.org/10.1246/cl.1983.1211>
6a. Kitamura T., Yamane M.: J. Chem. Soc., Chem. Commun. 1995, 983. <https://doi.org/10.1039/c39950000983>
6b. Peña D., Escudero S., Pérez D., Guitián E., Castedo L.: Angew. Chem., Int. Ed. 1998, 37, 2659. <https://doi.org/10.1002/(SICI)1521-3773(19981016)37:19<2659::AID-ANIE2659>3.0.CO;2-4>
6c. Yoshikawa E., Radhakrishnan K. V., Yamamoto Y.: J. Am. Chem. Soc. 2000, 122, 7280. <https://doi.org/10.1021/ja001205a>
6d. Yoshikawa E., Yamamoto Y.: Angew. Chem. Int. Ed. 2000, 39, 173. <https://doi.org/10.1002/(SICI)1521-3773(20000103)39:1<173::AID-ANIE173>3.0.CO;2-F>
6e. Yoshikawa E., Radhakrishnan K. V., Yamamoto Y.: Tetrahedron Lett. 2000, 41, 729. <https://doi.org/10.1016/S0040-4039(99)02114-0>
6f. Radhakrishnan K. V., Yoshikawa E., Yamamoto Y.: Tetrahedron Lett. 1999, 40, 7533. <https://doi.org/10.1016/S0040-4039(99)01526-9>
6g. Yoshida H., Watanabe M., Fukushima H., Ohshita J., Kunai A.: Org. Lett. 2004, 6, 4049. <https://doi.org/10.1021/ol048298b>
6h. Yoshida H., Fukushima H., Ohshita J., Kunai A.: Angew. Chem. Int. Ed. 2004, 43, 3935. <https://doi.org/10.1002/anie.200460009>
6i. Yoshida H., Fukushima H., Ohshita J., Kunai A.: J. Am. Chem. Soc. 2006, 128, 11040. <https://doi.org/10.1021/ja064157o>
7a. Yoshida H., Shirakawa E., Honda Y., Hiyama T.: Angew. Chem. Int. Ed. 2002, 41, 3247. <https://doi.org/10.1002/1521-3773(20020902)41:17<3247::AID-ANIE3247>3.0.CO;2-P>
7b. Yoshida H., Watanabe M., Ohshita J., Kunai A.: Chem. Commun. 2005, 3292. <https://doi.org/10.1039/b505392g>
7c. Peña D., Pérez D., Guitián E.: Angew. Chem. Int. Ed. 2006, 45, 2; and references therein.
7d. Liu Z., Larock R. C.: Org. Lett. 2003, 5, 4673. <https://doi.org/10.1021/ol0358612>
7e. Liu Z., Larock R. C.: J. Org. Chem. 2006, 71, 3198. <https://doi.org/10.1021/jo0602221>
8a. Jin T., Kamijo S., Yamamoto Y.: Tetrahedron Lett. 2004, 45, 9435. <https://doi.org/10.1016/j.tetlet.2004.10.103>
8b. Kamijo S., Jin T., Yamamoto Y.: J. Org. Chem. 2002, 67, 7413. <https://doi.org/10.1021/jo026147l>
8c. Jin T., Kamijo S., Yamamoto Y.: Eur. J. Org. Chem. 2004, 3789. <https://doi.org/10.1002/ejoc.200400442>
8d. Kamijo S., Jin T., Huo Z., Yamamoto Y.: J. Org. Chem. 2004, 69, 2386. <https://doi.org/10.1021/jo035292b>
8e. Kamijo S., Jin T., Huo Z., Yamamoto Y.: J. Am. Chem. Soc. 2003, 125, 7786. <https://doi.org/10.1021/ja034191s>
9a. Jin T., Yamamoto Y.: Angew. Chem. Int. Ed. 2007, 46, 3323. <https://doi.org/10.1002/anie.200700101>
9b. Liu Z., Shi F., Martinez P. D. G., Raminelli C., Larock R. C.: J. Org. Chem. 2008, 73, 219. <https://doi.org/10.1021/jo702062n>
10a. The 1H and 13C NMR spectra of compound 3a are identical with the literature data. Shmidt A., Merkel L., Eisfeld W.: Eur. J. Org. Chem. 2005, 2124.
10b. The structures of 3e, 3f, 3f′, 3g, 3g′ and 4d were unambiguously confirmed by spectroscopic methods, especially by NOE, COSY and HMBC analysis, see ref.9a.
11a. Lebedev A. Y., Khartulyari A. S., Voskoboynikov A. Z.: J. Org. Chem. 2005, 70, 596. <https://doi.org/10.1021/jo048671t>
11b. Cho C. S., Lim D. K., Heo N. H., Kim T.-J., Shim S. C.: Chem. Commun. 2004, 104. <https://doi.org/10.1039/b312154m>
11c. Song J. J., Yee N. K., Tetrahedron Lett. 2001, 42, 2937.
12a. Antilla J. C., Baskin J. M., Barder T. E., Buchwald S. L.: J. Org. Chem. 2004, 69, 5578. <https://doi.org/10.1021/jo049658b>
12b. Collot V., Bovy P. R., Rault S.: Tetrahedron Lett. 2000, 41, 9053. <https://doi.org/10.1016/S0040-4039(00)01650-6>
13a. Shintani R., Fu G. C.: J. Am. Chem. Soc. 2003, 125, 10778. <https://doi.org/10.1021/ja036922u>
13b. Dorn H., Otto A.: Chem. Ber. 1968, 101, 3287. <https://doi.org/10.1002/cber.19681010936>
13c. Dorn H., Otto A.: Angew. Chem., Int. Ed. Engl. 1968, 7, 214. <https://doi.org/10.1002/anie.196802141>
14a. Peña D., Pérez D., Guitián E., Castedo L.: J. Am. Chem. Soc. 1999, 121, 5827. <https://doi.org/10.1021/ja9907111>
14b. Peña D., Pérez D., Guitián E., Castedo L.: J. Org. Chem. 2000, 65, 6944. <https://doi.org/10.1021/jo000535a>
15. Yoshida H., Sugiura S., Kunai A.: Org. Lett. 2002, 4, 2767. <https://doi.org/10.1021/ol0262845>
16. Zrig S., Andrioletti B., Rose E., Colin J.: Tetrahedron Lett. 2005, 46, 1103. <https://doi.org/10.1016/j.tetlet.2004.12.095>
17. Su G., Mu H., Za D., Zeng L., Cativiela C., Hammer R. P., Yu K.: Synth. Commun. 2003, 33, 2873. <https://doi.org/10.1081/SCC-120022177>