Abstract
Methods published over the last 10 years for the production of substituted 1(2H)-isoquinolones, including those involving the use of organometallic compounds, are discussed.
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REFERENCES
I. W. Southon and J. Buckingham (Eds.), Dictionary of Alkaloids, Chapman and Hall, Vol. 1, New York (1989), p. 347.
M. Shamma and J. L. Moniot, Isoquinoline Alkaloids Research, 1972-1977, Plenum Press, New York, London (1978), p. 57.
S. Yu. Yunusov, Alkaloids[in Russian], Fan, Tashkent (1981), p. 119.
M. Shamma, in: The Isoquinoline Alkaloids, Chemistry and Pharmacology(Eds. A. T. Blomquist and H. Wasserman ), Academic Press, New York (1972), p. 90.
M. Shamma and J. E. Foy, Tetrahedron Lett., 2249 (1975).
I. R. Bick, J. B. Bremmer, T. L. Van, and P. Wiriyachitra, J. Nat. Prod., 49, 373 (1986); Ref. Zh. Khim., 2E115 (1987).
M. J. Fisher, B. P. Gunn, S. Um, and J. A. Jakubowski, Tetrahedron Lett., 38, 5747 (1997).
J. Berger and R. D. Clark, US Patent No. 5491148; Chem. Abstr., 124, 317007 (1996).
N. Okegawa and M. Kawamura, US Patent No. 5059607; Chem. Abstr., 114, 228918 (1991).
J. H. Hutchinson, J. J. Cook, K. M. Brashear, M. J. Breslin, J. D. Glass, R. J. Gould, W. Halczenko, M. A. Holahan, R. J. Lynch, G. R. Sitko, M. T. Stranieri, and G. D. Hartman, J. Med. Chem., 39, 4583 (1996).
H. Natsugari, H. Shirafuji, and T. Doi, US Patent No. 5523305; Chem. Abstr., 120, 134310 (1994).
T. S. Sulkovski and M. A. Wille, US Patent No. 3452027; Chem. Abstr., 71, 112830 (1969).
K. Kubo, N. Ito, I. Souzu, Y. Isomura, and H. Homma, Ger. Offen 2828528; Chem. Abstr., 90, 168468 (1979).
O. Senda, O. Ohtani, E. Katho, H. Miyake, and K. Fujiwara, Ger. Offen 3031574; Chem. Abstr., 95, 132692 (1981).
M. Hasegava, K. Shirai, K. Matsumoto, Y. Suzuki, and I. Takahasi, US Patent No. 544 1962; Chem. Abstr., 121, 912 (1994).
A. G. Nemazanyi, Yu. M. Volovenko, T. A. Silaeva, M. Yu. Kornilov, F. S. Babichev, S. A. Vasil'ev, and M. S. Luk'yannikov, Inventor's Certificate No. 1796 624; Byull. Izobr., No. 7, 79 (1993).
B. Bonnaud, A. Carlessi, and D. C. H. Bigg, J. Heterocycl. Chem., 30, 257 (1993).
J. H. Van Duzer and D. M. Roland, US Patent No. 5334600; Chem. Abstr., 122, 314462 (1995).
I. V. Ekhato and H. C. Che, J. Labelled Comp., 34, 627 (1994).
M. J. Ashton, A. W. Bridge, R. K. Chambers, D. I. Dron, G. Fenton, and N. V. Harris, European Patent No. 326386; Chem. Abstr., 112, 158072 (1990).
H. Natsugari and H. Ikeda, Jpn. Patent No. 03112967; Chem. Abstr., 115, 158988 (1991).
S. Senda, O. Ohtani, E. Katho, M. Nagasaka, H. Miyake, K. Fujiwara, and M. Tanaka, Fr. Demande2502619; Chem. Abstr., 98, 71955 (1983).
S. Senda, O. Ohtani, E. Katho, M. Nagasaka, H. Miyake, K. Fujiwara, and M. Tanaka, Ger. Offen 3211501; Chem. Abstr., 98, 198048 (1983).
H. Natsugari, T. Imamoto, and Y. Ichimori, US Patent No. 5527811; Chem. Abstr., 123, 198640 (1995).
B. Gabrielson, T. P. Monath, J. W. Huggins, D. F. Kefauer, G. R. Pettit, G. Groszek, M. Hollingshead, J. J. Kirsi, W. M. Shannon, E. M. Schubert, J. Dare, B. Ugerkar, M. Ussery, and M. I. Phelan, J. Nat. Prod., 55, 1569 (1992); Ref. Zh. Khim., 12E58 (1993).
N. Chida, M. Ohtsuka, and S. Ogawa, Tetrahedron Lett., 32, 4525 (1991).
T. Hudlicky and H. F. Olivo, J. Am. Chem. Soc., 114, 9694 (1992).
T. Hudlicky, H. F. Olivo, and B. McKibben, J. Am. Chem. Soc., 116, 5108 (1994).
T. Hudlicky and A. J. Thorpe, J. Chem. Soc. Chem. Commun., 1993 (1996).
M. C. McIntosh and S. M. Weinreb, J. Org. Chem., 58, 4823 (1993).
B. M. Trost and S. R. Pulley, J. Am. Chem. Soc., 117, 10143 (1995).
S. Andreae, in: Houben-Weyl, Methoden der Organischen Chemie(Ed. R. P. Kreher), Georg Thieme Verlag, Stuttgart, New York, E7a, Part 1, p. 571 (1991).
S. Gabriel and J. Colman, Chem. Ber., 33, 980 (1900).
M. C. Delcey, C. Huel, and E. Bisagni, Heterocycles, 41, 1721 (1995).
J. E. Semple, R. M. Rydzewski, and G. Gardner, J. Org. Chem., 61, 7967 (1996).
C.-Y. Cheng, H.-B. Tsai, and M.-S. Lin, J. Heterocycl. Chem., 32, 73 (1995).
R. C. Thompson and J. Kallmerten, J. Org. Chem., 55, 6076 (1990).
K.-Q. Ling, X.-Y. Chen, H.-K. Fun, X.-Y. Huang, and J.-H. Xu, J. Chem. Soc. Perkin Trans. 1, 4147 (1998).
O. Duval and L. M. Gomes, Tetrahedron, 46, 1253 (1990).
J. W. Cornforth and D. Ming-hui, J. Chem. Soc. Perkin Trans. 1, 1463 (1990).
M. A. Haimova, N. M. Mollov, S. C. Ivanova, A. I. Dimitrova, and V. I. Ognyanov, Tetrahedron, 33, 331 (1977).
M. Cushman and E. J. Madaj, J. Org. Chem., 52, 907 (1987).
M. Cushman and J. K. Chenn, J. Org. Chem., 52, 1517 (1987).
M. S. Mayadeo, S. J. Kulkarni, and K. D. Deodhar, Synthesis, 87 (1990).
M. Jayaraman, P. E. Fanwick, and M. Cushman, J. Org. Chem., 63, 5736 (1998).
F. T. Smith and R. V. Atigadda, J. Heterocycl. Chem., 28, 1813 (1991).
A. Georgieva, E. Stanoeva, S. Spassov, J. Macicek, O. Angelova, M. Haimova, and N. De Kimpe, Tetrahedron, 47, 3375 (1991).
D. Hellwinkel and K. Göke, Synthesis, 1135 (1995).
A. Sugimoto, H. Shinba-Tanaka, and M. Ishikava, Synthesis, 431 (1995).
K. Unverferth, R. Dörre, B. Körner, H. Scheibe, and E. Morgenstern, Arch. Pharm., 324, 809 (1991).
J. Dusemund and T. Hardt, Arch. Pharm., 321, 41 (1988).
S. Yamaguchi, Y. Uchiuzoh, and K. Sanada, J. Heterocycl. Chem., 32, 419 (1995).
S. Ohta and S. Kimoto, Tetrahedron Lett., 2279 (1975).
M. Khaldi, F. Chrétien, and Y. Chapleur, Tetrahedron Lett., 36, 3003 (1995).
G. E. Keck, S. F. McHardy, and J. A. Murry, J. Am. Chem. Soc., 117, 7289 (1995).
T. Minami, A. Nishimoto, and M. Hanaoka, Tetrahedron Lett., 36, 9505 (1995).
L. W. Deady and N. H. Quazi, Synth. Commun., 25, 309 (1995).
R. Connors, E. Tran, and T. Durst, Can. J. Chem., 74, 221 (1996).
R. Adams (Ed.), Organic Reactions[Russian translation], IL, Moscow (1953), p. 98.
M. G. Banwell and A. W. Wu, J. Chem. Soc. Perkin Trans. 1, 2671 (1994).
M. G. Banwell, C. J. Cowden, and M. F. Mackay, Chem. Soc. Chem. Commun., 61 (1994).
X.-J. Wang, J. Tan, and K. Grozinger, Tetrahedron Lett., 39, 6609 (1998).
A. G. Schultz, S. J. Kirincich, and R. Rahm, Tetrahedron Lett., 36, 4551 (1995).
M. G. Banwell, C. J. Cowden, and R. W. Gable, J. Chem. Soc. Perkin Trans. 1, 3515 (1994).
D. Gonzalez, T. Martinot, and T. Hudlicky, Tetrahedron Lett., 40, 3077 (1999).
H. Akgün and T. Hudlicky, Tetrahedron Lett., 40, 3081 (1999).
A. F. Khlebnikov, Author's Abstract of Doctoral Thesis[in Russian], St. Petersburg (1998).
F. Eloy and A. Deryckere, Helv. Chim. Acta, 52, 1755 (1969).
I. V. Ekhato and C. C. Huang, J. Labelled Comp., 34, 627 (1994).
J. M. Berry and M. D. Threadgill, J. Labelled Comp., 38, 935 (1996).
J. M. Berry and M. D. Threadgill, J. Labelled Comp., 39, 453 (1997).
C. Croisy-Delcey, E. Bisagni, C. Huel, D. Zilberfarb, and A. Croisy, J. Heterocycl. Chem., 28, 65 (1991).
T. Okegawa and M. Kavamura, Japanese Patent Appl.386876; Ref. Zh. Khim., 18O75P (1992).
T. Kitamura, S. Kobayashi, and H. Taniguchi, J. Org. Chem., 55, 1801 (1990).
L. Balizs, M. Nyerges, I. Kidas, and L. Töke, Synthesis, 1373 (1995).
G. Simig, Synlett, (1990).
M. Schlosser and G. Simig, Tetrahedron Lett., 32, 1965 (1991).
E. Lete, M. I. Collado, N. Sotomayor, and T. Vicente, J. Heterocycl. Chem., 32, 1751 (1995).
P. Beak, S. T. Kerrick, and D. J. Gallagher, J. Am. Chem. Soc., 115, 10628 (1993).
J. Cimpora, E. Gutiérrez, A. Monge, M. L. Poveda, C. Ruiz, and E. Carmona, Organometallics, 12, 4025 (1993).
X. Tian, T. Hudlicky, and K. Königsberger, J. Am. Chem Soc., 117, 3643 (1995).
G. E. Keck and T. T. Wager, J. Org. Chem., 61, 8366 (1996).
T. Sakamoto, N. Miura, Y. Kondo, and H. Yamanaka, Chem. Pharm. Bull., 34, 2760 (1986).
R. D. Clark and Jahangir, J. Org. Chem., 53, 2378 (1988).
K. Unverferth, R. Dörre, B. Korner, H. Sheibe, D. Lohmann, and G. Laban, Ger. Pat.287032; Chem. Abstr., 115, 29146 (1991).
S. Yamaguchi, M. Yoshida, I. Miyajima, T. Araki, and Y. Hirai, J. Heterocycl. Chem., 32, 1517 (1995).
T. Ross Kelly, S. H. Bell, N. Ohashi, and R. J. Armstrong-Chong, J. Am. Chem. Soc., 110, 6471 (1988).
A. Nagarajan and T. R. Balasubramanian, Indian J. Chem., 28B, 67 (1989).
T. G. Kutateladze, A. N. Fedotov, and S. S. Mochalov, Inventor's Certificate No. 1502570; Byull. Izobr., No. 31, 134 (1989).
R. S. Mali, B. K. Kulkarni, and K. Shankaran, Synthesis, 329 (1982).
V. Snieckus, Chem. Rev., 90, 879 (1990).
R. D. Clark, Jahangir, and J. A. Langston, Can. J. Chem., 72, 23 (1994).
V. G. Gore and N. S. Narasimhan, J. Chem. Soc. Perkin Trans. 1, 481 (1988).
L. E. Fisher, J. M. Caroon, Jahangir, S. R. Stabler, S. Lundberg, and J. M. Muchowski, J. Org. Chem., 58, 3643 (1993).
M. U. Koller, A. C. Church, C. L. Griffith, M. A. Hines, R. L. Lachicotte, R. A. Tailor, and Ch. F. Beam, Synth. Commun., 26, 1763 (1996).
J.-C. Cuevas and V. Snieckus, Tetrahedron Lett., 30, 5837 (1989).
A. G. Nemazanyi, Yu. M. Volovenko, F. S. Babichev, and T. A. Silaeva, Inventor's Certificate No. 1728 242; Byull. Izobr., No. 15, 100 (1992).
F. S. Babichev, Yu. M. Volochenko, É. F. Gavrilova, M. L. Kolomiets, A. G. Nemazanyi, L. A. Pilipenko, and T. A. Silaeva, Inventor's Certificate No. 1659 413; Ref. Zh. Khim., 3N141P (1992).
A. G. Nemazanyi, Yu. M. Volovenko, T. A. Silaeva, M. Yu. Kornilov, and F. S. Babichev, Khim. Geterotsikl. Soedin., 378 (1991).
A. G. Nemazanyi, Yu. M. Volovenko, T. A. Silaeva, M. Yu. Kornilov, and F. S. Babichev, Khim. Geterotsikl. Soedin., 1104 (1991).
T. Izumi, Y. Nishimoto, K. Kohei, and A. Kasahara, J. Heterocycl. Chem., 27, 1419 (1990).
J. S. Mahanty, De Mahuya, and N. G. Kundu, J. Chem. Soc. Perkin Trans. 1, 2577 (1997).
R. C. Larock, C.-L. Liu, H. H. Lan, and S. Varaprath, Tetrahedron Lett., 25, 4459 (1984).
D. P. Meiris, E. Guitiin, and L. Castedo, Tetrahedron Lett., 31, 2331 (1990).
C. Gonzilez, E. Guitiin, and L. Castedo, Tetrahedron Lett., 37, 405 (1996).
A. S. Kiselyov, Tetrahedron Lett., 36, 493 (1995).
L. E. Fisher, J. M. Muchowski, and R. D. Clark, J. Org. Chem., 57, 2700 (1992).
Couture, E. Deniau, P. Woisel, P. Grandclaudon, and J. F. Carpentier, Tetrahedron Lett., 37, 3697 (1996).
A. Couture, E. Deniau, P. Grandclaudon, and P. Woisel, Tetrahedron, 52, 4433 (1996).
A. Couture, H. Cornet, E. Deniau, P. Grandclaudon, and S. Lebrun, J. Chem. Soc. Perkin Trans. 1, 469 (1997).
A. Couture, E. Deniau, S. Lebrun, and P. Grandclaudon, J. Chem. Soc. Perkin Trans. 1, 789 (1999).
R. Grigg, V. Loganathan, and V. Santhakumar, Tetrahedron Lett., 32, 687 (1991).
R. Grigg, V. Sridharan, P. Stevenson, and S. Sukirthalingam, Tetrahedron, 45, 3557 (1989).
R. Grigg, V. Sridharan, and L.-H. Xu, J. Chem. Soc. Chem. Commun., 1903 (1995).
I. R. Girling and D. A. Widdowson, J. Chem. Soc. Perkin Trans. 1, 1317 (1988).
L. F. Tietze and O. Burhardt, Lieb. Ann., 1153 (1995).
D. A. Goff and R. N. Zuckermann, J. Org. Chem., 60, 5748 (1995).
A. G. Schultz, M. A. Holoboski, and M. S. Smyth, J. Am. Chem. Soc., 115, 7904 (1993).
W. M. Lee, W. H. Chan, and E. T. T. Chan, J. Chem. Soc. Perkin Trans. 1, 309 (1992).
I. Datta, T. K. Das, and S. Ghosh, Tetrahedron, 46, 6821 (1990).
J.-C. Gramain, S. Mavel, Y. Train, and D. Vallée-Goyet, Tetrahedron, 47, 7287 (1991).
J. L. Esker and M. Newcomb, J. Org. Chem., 58, 4933 (1993).
J. H. Rigby and V. Gupta, Synlett, 547 (1995).
A. Missoum, M.-E. Sinibaldi, D. Vallée-Goyet, and J.-C. Gramain, Synth. Commun., 27, 453 (1997).
A. Couture, E. Deniau, P. Grandclaudon, and S. Lebrun, Tetrahedron Lett., 37, 7749 (1996).
N. Cholleton and S. Z. Zard, Tetrahedron Lett., 39, 7295 (1998).
A. Cobas, E. Guitiin, and L. Castedo, J. Org. Chem., 58, 3113 (1993).
A. P. Venkov and S. M. Statkova-Abeghe, Tetrahedron, 52, 1451 (1996).
E. Dominguez, M. E. Martknez de, L. Carrillo, and R. Fancnis, Tetrahedron, 47, 9253 (1991).
Y. Shigeyuki and A. Kawa, Chem. Pharm. Bull., 37, 3380 (1989).
A. L. Stanley and S. P. Stanford, J. Heterocycl. Chem., 32, 569 (1995).
K. A. Hedley and S. P. Stanford, Tetrahedron, 48, 743 (1992).
G. R. Lenz and C. Castanza, J. Org. Chem., 53, 1176 (1988).
K. Maeda, M. Yoko, K. Isozaki, S. Yamada, and Y. Mori, J. Chem. Soc. Perkin Trans. 2, 121 (1996).
B.-X. Zhao, Y. Yu, and Sh. Eguchi, Org. Prep. and Proced. Int., 29, 185 (1997).
Yu. V. Shklyaev, V. A. Glushkov, N. B. Belogub, and I. L. Misyura, Khim. Geterotsikl. Soedin., 800 (1996).
B. E. Maryanoff, H.-C. Zhang, A. B. Reitz, G. C. Leo, and W. J. Jones, Tetrahedron Lett., 34, 7247 (1993).
D. Heber, U. Holzgrabe, and W. Werra, Arch. Pharm., 326, 785 (1993).
C. Vaccher, P. Berthelot, M. Devergnies, M. Debaert, J.-P. Bonte, and C. Viel, J. Heterocycl. Chem., 26, 811 (1989).
C. E. Thomas, P. Bernardelli, S. M. Bowen, St. F. Chaney, D. Friedrich, D. A. Janovick, B. K. Jones, F. J. Keeley, J. H. Kehne, B. Ketteler, D. F. Ohlweiler, L. A. Paquette, D. J. Robke, and Th. L. Fevig, J. Med. Chem., 39, 4997 (1996).
M. Kawase, J. Chem. Soc. Chem. Commun., 1328 (1990).
S. F. Mason and D. R. Roberts, Chem. Commun., 467 (1967).
J. H. Van Duzer and D. M. Roland, Eur. Pat. No. 526402; Chem. Abstr., 119, 8694 (1993).
C. Cirrincione, A. M. Almerico, G. Dattolo, E. Aiello, P. Diana, and F. Mingoia, J. Heterocycl. Chem., 29, 1309 (1992).
H. Tomisawa, R. Fugita, H. Kato, K. Hayasaka, T. Kamimura, and H. Hongo, Chem. Pharm. Bull., 36, 1882 (1988).
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Glushkov, V.A., Shklyaev, Y.V. Synthesis of 1(2H)-Isoquinolones. (Review). Chemistry of Heterocyclic Compounds 37, 663–687 (2001). https://doi.org/10.1023/A:1011958810129
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DOI: https://doi.org/10.1023/A:1011958810129