Abstract
Methods for the synthesis of heteroaryl-substituted 1,4-benzo- and 1,4-naphthoquinones with a C-C bond between the heterocycle and quinone fragments are reviewed.
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REFERENCES
S. Patai (editor), The Chemistry of the Quinonoid Compounds, Pt. 1 and 2, Wiley, London et al. (1974), 1274 pp.
S. Patai and Z. Rappoport (editors), The Chemistry of the Quinonoid Compounds, Vol. 2, Pt. 1 and 2, Wiley, Chichester (1988), 1711 pp.
C. Vazquez, J. C. Calabrese, D. A. Dixon, and J. S. Miller, J. Org. Chem., 58, 65 (1993).
O. Ya. Neilands, Latv. PSR ZA Vestis. Fiz. un tehn. zin. ser., No. 6, 63 (1981).
R. H. Thompson, Naturally Occurring Quinones, Vol. 1–3, Chapman and Hall., London.
S. Spyroudis, Molecules, 5, 1291 (2000).
P. R. W. Middleton and J. Patrick, in: S. Patai and Z. Rappoport (editors), The Chemistry of the Quinonoid Compounds, Vol. 2, Pt. 2, Wiley, Chichester et al. (1988), p. 1099.
M. Tisler, Adv. Heterocycl. Chem., 45, 37 (1989).
G. D. Harris, A. Nguyen, H. App, P. Hirth, G. McMahon, and C. Tang, Org. Lett., 1, 431 (1999).
M. C. Pirrung, K. Park, and Z. Li, Org. Lett., 3, 365 (2001).
T. Itahara, J. Org. Chem., 50, 5546 (1985).
B. Zhang, G. Salituro, D. Szalkowski, Z. Li, Y. Zhang, I. Royo, D. Vilella, M. T. Diez, F. Pelaez, C. Ruby, R. L. Kendall, X. Mao, P. Griffin, J. Calaycay, J. R. Zierath, J. V. Heck, R. G. Smith, and D. E. Moller, Science, 284, 974 (1999).
V. K. Tandon, R. V. Singh, S. Rai, R. B. Chor, and Z. Khan, Boll. Chim Farm., 141, 304 (2002).
J.-C. Henrion, B. Jacquet, M. Hocquaux, G. Barre, and C. Lion, Bull. Soc. Chim. Belg., 103, 163 (1994).
J.-C. Henrion, B. Jacquet, M. Hocquaux, C. Lion, and M. Hedayatullah, Bull. Soc. Chim. Belg., 105, 409 (1996).
A. K. El-Shafei, A. M. El-Sayed, A. Sultan, and H. Abdel-Ghany, Gazz. Chim. Ital., 120, 197 (1990).
A. A. Hassan, N. K. Mohamed, E. H. El Tamany, B. A. Ali, and A. E. Mourad, Monatsh. Chem., 126, 653 (1995).
F. Siberdt and J. Nasielski, Bull. Soc. Chim. Belg., 106, 85 (1997).
J. A. Valderrama, J. Benites, M. Cortes, D. Pessoa-Mahana, E. Prina, and A. Fournet, Tetrahedron, 58, 881 (2002).
J. A. Valderrama, J. Benites, M. Cortes, D. Pessoa-Mahana, M. Preite, and J. Benites, Tetrahedron Lett., 41, 3563 (2000).
J. M. Ribo and C. Acero, Liebigs Ann. Org. Bioorg. Chem., 509 (1995).
C. Lion, R. Baudry, M. Hedayatullah, L. Da Conceicao, M. Hocquaux, S. Genard, and J. Maignan, J. Heterocycl. Chem., 37, 1635 (2000).
H. Laatsch, B. Renneberg, U. Hanefeld, M. Kellner, H. Pudleiner, G. Hamprecht, H.-P. Kraemer, and H. Alike, Chem. Pharm. Bull., 43, 537 (1995).
D. R. Mckean, G. Parrinello, A. F. Renaldo, and J. K. Stille, J. Org. Chem., 52, 422 (1987).
X. Deng and L. S. Liebeskind, J. Am. Chem. Soc., 123, 7703 (2001).
S. Yoshida, H. Kubo, T. Saika, and S. Katsumura, Chem. Lett., 139 (1996).
M. C. Pirrung, Z. Li, K. Park, and J. Zhu, J. Org. Chem., 67, 7919 (2002).
N. Tamayo, A. M. Echavarren, and M. C. Paredes, J. Org. Chem., 56, 6488 (1991).
A. M. Echavarren, N. Tamayo, and D. J. Cardenas, J. Org. Chem., 59, 6075 (1994).
K. W. Stagliano, H. C. Malinakova, and J. S. Harwood, J. Org. Chem., 66, 7530 (2001).
K. W. Stagliano and H. C. Malinakova, J. Org. Chem., 64, 8034 (1999).
J. O. Karlsson, N. V. Nguyen, L. D. Poland, and H. W. Moore, J. Am. Chem. Soc., 107, 3392 (1985).
L. D. Poland, J. O. Karlsson, S. T. Perri, R. Schwabe, S. L. Xu, S. Patil, and H. W. Moore, J. Am. Chem. Soc., Ill, 975 (1989).
G. Bringmann, R. Gotz, P. A. Keller, R. Walter, M. R. Boyd, F. Lang, A. Garcia, J. J. Walsh, I. Tellitu, K. V. Bhaskar, and T. R. Kelly, J. Org. Chem., 63, 1090 (1998).
L. S. Liebeskind and S. W. Riesinger, J. Org. Chem., 58, 408 (1993).
R. Asano, I. Moritani, Y. Fujiwara, and Sh. Teranishi, Bull. Chem. Soc. Jpn., 46, 663 (1973).
T. Itahara, Bull. Chem. Soc. Jpn., 69, 3239 (1996).
J. A. Valderrama, J. Benites, M. Cortes, H. Pessoa-Mahana, E. Prina, and A. Fournet, Bioorg. Med. Chem., 11, 4713 (2003).
J. S. Yadav, B. V. S. Reddy, and T. Swamy, Synthesis, 1, 106 (2004).
A. V. Reddy, K. Ravinder, T. V. Goud, P. Krishnaiah, T. V. Raju, and Y. Venkateswarlu, Tetrahedron Lett., 44, 6257 (2003).
J. S. Yadav, B. V. S. Reddy, and T. Swamy, Tetrahedron Lett., 44, 9121 (2003).
U. Pindur, Y.-S. Kirn, and D. Schollmeyer, J. Heterocycl. Chem., 31, 377 (1994).
G. A. Kraus and I. Kim, J. Org. Chem., 68, 4517 (2003).
Y. Tanoue, A. Terada, H. Taniguchi, T. Okuma, H. Kaai, M. Anan, Y. Kakara, M. Doi, and Sh.-i. Morishita, Bull. Chem. Soc. Jpn., 66, 3712 (1993).
C. Lion, R. Baudry, M. Hedayatullah, L. Conceicao, S. Genard, and J. Maignan, J. Heterocycl. Chem., 39, 125 (2002).
J.-C. Henrion, B. Jacquet, M. Hocquaux, G. Barre, M. Hedayatullah, and C. Lion, Bull. Soc. Chim. Belg., 105, 557 (1996).
J.-C. Henrion, B. Jacquet, M. Hocquaux, C. Lion, and G. Barre, Bull. Soc. Chim. Belg., 104, 521 (1995).
J. Sohn, B. Kiburz, Z. Li, L. Deng, A. Safi, M. C. Pirrung, and J. Rudolph, J. Med. Chem., 46, 2580 (2003).
M. C. Pirrung, L. Deng, Z. Li, and K. Park, J. Org. Chem., 67, 8374 (2002).
A. Sen and V. Krishnan, Tetrahedron Lett., 37, 8437 (1996).
H. B. Wood, Jr., R. Black, G. Salituro, D. Szalkowski, Z. Li, Y. Zhang, D. E. Moller, B. Zhang, and A. B. Jones, Bioorg. Med. Chem., 10, 1189 (2000).
A. Kaji, K. Kimura, M. Teranishi, N. Kiriyama, M. Nomura, and K.-i. Miyamoto, Chem. Pharm. Bull., 46, 1325 (1998).
A. Kaji, R. Saito, Y. Hata, and N. Kiriyama, Chem. Pharm. Bull., 47, 77 (1999).
M. A. Brimble and E. Ireland, J. Chem. Soc., Perkin Trans. 1, 3109 (1994).
M. C. Carreno, J. L. Garcia Ruano, A. Urbano, C. Z. Remor, and Y. Arroyo, Tetrahedron: Asymmetry, 10, 4357 (1999).
M. A. Brimble, C. Burgess, R. Halim, and M. Petersson, and J. Ray, Tetrahedron, 60, 5751 (2004).
M. A. Brimble, R. Halim, and M. Petersson, Tetrahedron Lett., 43, 4777 (2002).
K. Maruyama and H. Tamiaki, Bull. Chem. Soc. Jpn., 60, 1847 (1987).
M. Yamaji, M. Kurumi, H. Kimura, and H. Shizuka, Phys. Chem. Chem. Phys., 1, 1859 (1999).
L. A. Al-Razzak, D. Schwepler, Ch. J. Decedue, J. Balzarini, E. De Clercq, and M. P. Mertes, J. Med. Chem., 30, 409 (1987).
K. Kobayashi, M. Suzuki, H. Takeuchi, A. Konishi, H. Sakurai, and H. Suginome, J. Chem. Soc., Perkin Trans. 1, 1099 (1994).
G. A. Kraus and I. Kirn, Tetrahedron, 59, 7935 (2003).
H. R. El-Seedi, S. Yamamura, and S. Nishiyama, Tetrahedron, 58, 7485 (2002).
M. Iyoda, F. Sultana, A. Kato, M. Yoshida, Y. Kuwatani, M. Komatsu, and S. Nagase, Chem. Lett., 63 (1997).
B. M. Illescas and N. Martin, J. Org. Chem., 65, 5986 (2000).
A. M. Thompson, H. D. H. Showalter, and W. A. Denny, J. Chem. Soc., Perkin Trans. 1, 12, 1843 (2000).
S. Ruchirawat and T. Mutarapat, Tetrahedron Lett., 42, 1205 (2001).
V. M. Lyubchanskaya, S. A. Savina, L. M. Alekseeva, and V. G. Granik, Mendeleev Commun., 13, 29 (2003).
Q. Lu, W. Liu, J. Ding, J. Cai, and W. Duan, Bioorg. Med. Chem Lett., 12, 1375 (2002).
H. R. Mohan and A. S. Rao, Synthetic Comm., 23, 2579 (1993).
M. A. Rerghot, Rev. Roum. Chim., 48, 197 (2003).
C.-Y. Chang, L.-J. Huang, J.-P. Wang, C.-M. Teng, S.-C. Chen, and S.-C. Kuo, Chem. Pharm. Bull., 48, 964 (2000).
U. Kucklaender, P. Ulmer, and G. Zerta, Arch. Pharm., 322, 437 (1989).
B. Alcaide, P. Almendros, and N. R. Salgado, Tetrahedron Lett., 42, 1503 (2001).
K. Kloc, J. Mlochowski, L. Syper, and M. Mordarski, J. Prakt. Chem., 328, 419 (1986).
M. A. Hassan, A. O. Maslat, M. Abussaud, I. Ch. Ahmed, and A. S. AlKofahi, Arch. Pharm., 331, 385 (1998).
R. Valters, G. Karlivans, J. Gulbis, M. Utinans, and A. Bace, Phosphorus, Sulfur, and Silicon, 95–96, 457 (1994).
R. E. Valter, E. E. Liepin'sh, G. A. Karlivan, V. R. Zin'kovska, and M. F. Utinan, Zh. Org. Khim., 21, 436 (1985).
G. A. Karlivan, R. E. Valter, A. E. Batse, and Yu. V. Gulbis, Khim. Geterotsikl. Soedin., 463 (1996).
R. Valters, G. Karlivans, A. Bace, and J. Gulbis, Phosphorus, Sulfur, and Silicon, 120–121, 411 (1997).
G. A. Karlivan, R. E. Valter, and Yu. V. Gulbis, Khim. Geterotsikl. Soedin., 1055 (1998).
Yu. V. Gulbis and R. E. Valters, Khim. Geterotsikl. Soedin., 1556 (2001).
M. F. Utinan, R. E. Valter, G. A. Karlivan, E. E. Liepin'sh, and A. S. Edzhinya, Khim. Geterotsikl. Soedin., 692 (1988).
R. E. Valter, G. A. Karlivan, M. F. Utinan, and Yu. V. Gulbis, Sib. Khim. Zh., No. 4, 39 (1992).
M. Utinans, J. Gulbis, R. Valters, E. Liepins, G. Karlivans, and A. Edzina, Khim. Geterotsikl. Soedin., 410 (1991).
M. F. Utinan, Yu. V. Gulbis, R. E. Valter, and G. A. Karlivan, Khim. Geterotsikl. Soedin., 427 (1992).
M. F. Utinan, R. E. Valter, and G. A. Karlivan, Khim. Geterotsikl. Soedin., 1430 (1989).
G. A. Karlivan, R. E. Valter, and M. F. Utinan, Khim. Geterotsikl. Soedin., 849 (1985).
G. Karlivans, J. Gulbis, R. Valters, A. Bace, and R. Kampare, Latvian J. Chem., 99 (1994).
Yu. V. Gulbis, M. F. Utinan, G. A. Karlivan, and R. E. Valter, Khim. Geterotsikl. Soedin., 424 (1992).
G. A. Karlivan, R. E. Valter, A. E. Batse, and Yu. V. Gulbis, Khim. Geterotsikl. Soedin., 1424 (1996).
Yu. V. Gulbis, R. E. Valter, G. A. Karlivan, and M. F. Utinan, Khim. Geterotsikl. Soedin., 111 (1994).
R. Valters, G. Karlivans, J. Gulbis, and A. Bace, Phosphorus, Sulfur, and Silicon, 153–154, 411 (1999).
G. A. Karlivan, R. E. Valter, and A. E. Bace, Khim. Geterotsikl. Soedin., 988 (1999).
G. Karlivans and R. Valters, Khim. Geterotsikl. Soedin., 1837 (2003).
G. A. Karlivans and R. E. Valters, Khim. Geterotsikl. Soedin., 939 (2004).
N. G. Batenko, R. E. Valter, and G. A. Karlivan, Khim. Geterotsikl. Soedin., 835 (2000).
N. Batenko, R. Valters, and G. Karlivans, Scientific Proceedings of RTU. Material Science and Applied Chemistry, 1, 99 (2003).
D. Buckley, H. Henbest, and P. Slade, J. Chem. Soc., 4891 (1957).
M. Alnabari and S. Bittner, Synthesis, 8, 1087 (2000).
K. Liu, L. Xu, D. Szalkowski, Z. Li, V. Ding, G. Kwei, S. Huskey, D. E. Moller, J. V. Heck, B. B. Zhang, and A. B. Jones, J. Med. Chem., 43, 3487 (2000).
K. Liu, H. B. Wood, and A. B. Jones, Tetrahedron Lett., 40, 5119 (1999).
X. Shi, Sk. R. Amin, and L. S. Liebeskind, J. Org. Chem., 65, 1650 (2000).
X. Shi and L. S. Liebeskind, J. Org. Chem., 65, 1665 (2000).
S. R. Pulley and J. P. Carey, J. Org. Chem., 63, 5275 (1998).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 803–833, June, 2005.
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Batenko, N.G., Karlivans, G. & Valters, R. Methods for the Synthesis of Heteroaryl-substituted 1,4-Benzo- and 1,4-Naphthoquinones. (Review). Chem Heterocycl Compd 41, 691–717 (2005). https://doi.org/10.1007/s10593-005-0210-8
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DOI: https://doi.org/10.1007/s10593-005-0210-8