none 10.3987/COM-08-11347 CLOCKSS Archive CLOCKSS Archive 5187 36255903 73640 20090216111438 10.13030 2024-06-24T16:35:00Z 2009-02-15T21:15:56Z 7 HETEROCYCLES HETEROCYCLES 0385-5414 HTCYAM 2008 75 7 A Facile Synthesis of Imidazo[1,5-b]pyridazines from 3-Formylchromones Sergey V. Ryabukhin Andrey S. Plaskon Dmitriy M. Volochnyuk Alexander N. Shivanyuk Andrey A. Tolmachev 2008 1765 COM-08-11347 10.3987/COM-08-11347 20090216111438 https://triggered.stanford.clockss.org/ServeContent?doi=10.3987%2Fcom-08-11347 https://triggered.edinburgh.clockss.org/ServeContent?doi=10.3987%2Fcom-08-11347 (a) A. D. Lebsack, B. Munoz, R. Pracitto, S. Venkatraman, B. Wang, and J. Gunzner, PCT Int. Appl. 2005, WO 2005041971 (Chem. Abstr., 2005, 142, 463735). (b) R. W. Clarke and A. W. Oxford, DE 2804909, 1978 (Chem. Abstr., 1979, 91, 57044). 10.1021/jm980413z (c) J. L. Collins, S. G. Blanchard, G. E. Boswell, P. S. Charifson, J. E. Cobb, B. R. Henke, E. A. Hull-Ryde, W. M. Kazmierski, D. H. Lake, L. M. Leesnitzer, J. Lehmann, J. M. Lenhard, L. A. Orband-Miller, Y. Gray-Nunez, D. J. Parks, K. D. Plunkett, and W.-Q. Tong, J. Med. Chem., 1998, 41, 5037. 10.1016/S0049-237X(08)70459-2 2. D. J. Knight, D. I. C. Scopes, R. Storer, and S. Holman, DE 3541358, 1986 (Chem. Abstr., 1986, 105, 173001). 10.1177/095632029800900302 (a) M. Renoud-Grappin, C. Fossey, G. Fontaine, D. Laduree, A. M. Aubertin, and A. Kirn, Antiviral Chem. Chemother., 1998, 9, 205. 10.1021/jm00076a005 (b) D. G. H. Livermore, R. C. Bethell, N. Cammack, A. P. Hancock, M. M. Hann, D. V. S. Green, R. B. Lamont, S. A. Noble, D. C. Orr, J. J. Payne, M. V. J. Ramsay, A. H. Shingler, C. Smith, R. Storer, C. Williamson, and T. Willson, J. Med. Chem., 1993, 36, 3784. 4. For related cyclization reaction of 1-amino-1H-imidazoles see: (a) T. Irrgang and R. Kempe, Eur. J. Inorg. Chem., 2005, 21, 4382. (b) N. N. Kolos, V. D. Orlov, B. V. Paponov, and O. V. Shishkin, Chem. Heterocycl. Compd. (Engl. Transl.), 1999, 35, 1207. (c) V. P. Kruglenko, A. A. Timoshin, V. A. Idzikovskii, N. A. Klyuev, and M. V. Povstyanoi, Ukr. Khim. Zh., 1988, 54, 612; Chem. Abstr. 1989, 110, 231554. (d) R. Brückner, J.-P. Lavergne, and P. Viallefont, Liebigs Ann. Chem., 1979, 639. (e) G. M. Golubushina, G. N. Poshtaruk, and V. A. Chuiguk, Chem. Heterocycl. Compd. (Engl. Transl.), 1974, 10, 735. (f) N. N. Kolos, V. D. Orlov, B. V. Paponov, and V. N. Baumer, Chem. Heterocycl. Compd. (Engl. Transl.), 1998, 34, 1189. (g) N. N. Kolos, T. V. Beryozkina, and V. D. Orlov, Mendeleev Commun., 2002, 12, 91. (h) X. Zhao and R. Zhang, Synth. Commun., 1995, 25, 3271. (a) S. V. Ryabukhin, A. S. Plaskon, D. M. Volochnyuk, and A. A. Tolmachev, Synlett, 2004, 2287. 10.1055/s-2007-983704 (b) S. V. Ryabukhin, A. S. Plaskon, D. M. Volochnyuk, and A. A. Tolmachev, Synthesis, 2007, 1861. 10.1055/s-2007-990790 (c) S. V. Ryabukhin, A. S. Plaskon, D. M. Volochnyuk, and A. A. Tolmachev, Synthesis, 2007, 3155. 10.1055/s-2006-950289 (a) S. V. Ryabukhin, A. S. Plaskon, D. M. Volochnyuk, and A. A. Tolmachev, Synthesis, 2006, 3715. (b) S. V. Ryabukhin, A. S. Plaskon, E. N. Ostapchuk, D. M. Volochnyuk, and A. A. Tolmachev, Synthesis, 2007, 417. 10.1055/s-2007-966003 (c) S. V. Ryabukhin, D. M. Volochnyuk, A. S. Plaskon, V. S. Naumchik, and A. A. Tolmachev, Synthesis, 2007, 1214. 10.1021/cc070073f (d) S. V. Ryabukhin, A. S. Plaskon, D. M. Volochnyuk, S. E. Pipko, A. N. Shivanyuk, and A. A. Tolmachev, J. Comb. Chem., 2007, 9, 1073. 10.1080/00397918708077331 7. G. J. Reddy, G. Sabitha, and A. V. S. Rao, Synth. Commun., 1987, 17, 1851. 10.1002/jhet.5570200434 8. For cyclization reaction of 4-amino-4H-1,2,4-triazoles as 1,3-NNC-binucleophiles see: (a) E. M. Essassi, R. Zniber, A. Bernardini, and P. Viallefont, J. Heterocycl. Chem., 1983, 20, 1015. (b) T. Okabe, B. Bhooshan, T. Novinson, I. W. Hillyard, G. E. Garner, and R. K. Robins, J. Heterocycl. Chem., 1983, 20, 735. (c) B. J. S. Bajwa and P. J. Sykes, J. Chem. Soc. Perkin Trans. 1, 1979, 3085. (d) K. C. Joshi and K. Dubey, Pharmazie, 1979, 34, 801. (e) H. G. O. Becker and H. Böttcher, Tetrahedron, 1968, 24, 2687. 10.1016/S0968-0896(99)00254-0 9. For cyclization reaction of 1-amino-1H-benzimidazole with 1,3-dicarbonyl compounds see: (a) T. Kaiya, S. Aoyama, and K. Kohda, Bioorg. Med. Chem., 2000, 8, 37. (b) T. Kaiya, T. Saga, Y. Yamagata, and K. Kohda, Bioorg. Med. Chem. Lett., 1998, 8, 2197. (c) V. V. Kuz‘menko, V. N. Komissarov, and A. M. Simonov, Chem. Heterocycl. Compd. (Engl. Transl.), 1983, 19, 314.