{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2024,9,16]],"date-time":"2024-09-16T14:29:01Z","timestamp":1726496941442},"reference-count":14,"publisher":"CLOCKSS Archive","issue":"9","content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["HETEROCYCLES"],"published-print":{"date-parts":[[2005]]},"DOI":"10.3987\/com-05-10447","type":"journal-article","created":{"date-parts":[[2009,2,17]],"date-time":"2009-02-17T08:32:10Z","timestamp":1234859530000},"page":"2189","source":"Crossref","is-referenced-by-count":4,"title":["Preparation of 1-Alkyl-2-aryl-1H-imidazo[4,5-b]pyridines from 2-Alkylamino-3-aminopyridines and Aromatic Aldehydes Using Air as an Oxidant"],"prefix":"10.13030","volume":"65","author":[{"given":"Mikhail","family":"Krasavin","sequence":"first","affiliation":[]},{"given":"Vladimir","family":"V. Kobak","sequence":"additional","affiliation":[]},{"given":"Tatiana","family":"Y. Bondarenko","sequence":"additional","affiliation":[]},{"given":"Dmitry","family":"V. Kravchenko","sequence":"additional","affiliation":[]}],"member":"5187","reference":[{"key":"10.3987\/COM-05-10447-1","unstructured":"1. R. L. Clark, A. A. Pessolano, T.-Y. Shen, D. P. Jocobus, H. Jones, V. J. Lotti, and L. M. Flataker, J. Med. Chem., 1978, 21, 965."},{"key":"10.3987\/COM-05-10447-2","doi-asserted-by":"crossref","unstructured":"2. I. K. Khanna, R. M. Weier, K. T. Lentz, L. Swenton, and D. C. Lankin, J. Org. Chem., 1995, 60, 960.","DOI":"10.1021\/jo00109a029"},{"key":"10.3987\/COM-05-10447-3","unstructured":"3. E. Nikola\u00ef, J. Goyard, T. Benchetrit, J.-M. Teulon, F. Caussade, A. Virone, C. Delchambre, and A. Cloarec, J. Med. Chem., 1993, 36, 1175."},{"key":"10.3987\/COM-05-10447-4","unstructured":"4. P. K. Chakravarty, E. M. Naylor, A. Chen, R. S. Chang, T. B. Chen, K. A. Faust, V. J. Lotti, S. D. Kivlighn, R. A. Gable, G. J. Zingaro, T. W. Schorn, L. W. Schaffer, T. P. Broten, P. K. S. Siegl, A. A. Patchett, and W. J. Greenlee, J. Med. Chem., 1994, 37, 4068."},{"key":"10.3987\/COM-05-10447-5","unstructured":"5. M. Oguchi, K. Wada, H. Honma, A. Tanaka, T. Kaneko, S. Sakakibara, J. Ohsumi, N. Serizawa, T. Fujiwara, H. Horikoshi, and T. Fujita, J. Med. Chem., 2000, 43, 3052."},{"key":"10.3987\/COM-05-10447-6","unstructured":"6. J. F. Kuethe, A. Wang, and I. W. Davies, J. Org. Chem., 2004, 69, 7752."},{"key":"10.3987\/COM-05-10447-7","doi-asserted-by":"crossref","unstructured":"7. (a) G. P. Zecchini, I. Torrini, and M. P. Paradisi, J. Heterocycl. Chem., 1985, 22, 313; (b) J. Heinicke, A. Oprea, M. K. Kindermann, T. Karpati, L. Nyulaszi, and T. Veszpremi, Chem. Europ. J., 1998, 4, 541.","DOI":"10.1002\/jhet.5570220427"},{"key":"10.3987\/COM-05-10447-8","unstructured":"8. (a) G. Pirisino, M. C. Alamanni, F. Savelli, F. Sparatore, P. Manca, and M. Satta, Farmaco Ed. Sci., 1983, 38, 330; (b) R. Iemura, M. Hori, T. Saito, and H. Ohtaka, Chem. Pharm. Bull., 1989, 37, 2723; (c) B. E. Tomczuk, C. R. Taylor, L. M. Moses, D. B. Sutherland, Y. S. Lo, D. N. Johnson, W. B. Kinnier, and B. F. Kilpatrick, J. Med. Chem., 1991, 34, 2993."},{"key":"10.3987\/COM-05-10447-9","unstructured":"9. We subsequently established the intermediacy of the aldimines (3) in the described process by detecting the presence of respective characteristic signals in the 1H NMR spectrum of the reaction mixture aliquot measured after 1 h of 2-alkylamino-3-aminopyridine (2a) reacting with aldehyde (4a): \u03b4 8.60 (s, C<U>H<\/U>=N, rel. int. 1H), 6.21 (t, J = 5.1 Hz, N<U>H<\/U>-CH2, rel. int. 1H), 4.10 (d, J = 7.0 Hz, OC<U>H<\/U>2CH3, rel. int. 2H), 3.27 (s, OC<U>H<\/U>3, rel. int. 3H), 1.35 (t, J = 7.0 Hz, OCH2C<U>H<\/U>3, rel. int. 3H). It was present in rather small concentration (~ 10 mol. %) and could not be detected by TLC analysis due to decomposition on silica gel."},{"key":"10.3987\/COM-05-10447-10","unstructured":"10. P. K. Dubey, R. V. Kumar, A. Naidu, and S. M. Kulkarni, Asian J. Chem., 2002, 14, 1129."},{"key":"10.3987\/COM-05-10447-11","doi-asserted-by":"crossref","unstructured":"11. M. Yu. Yutilov and L. I. Shcherbina, Chem. Heterocycl. Compounds, 1987, 23, 529.","DOI":"10.1007\/BF00476381"},{"key":"10.3987\/COM-05-10447-12","doi-asserted-by":"crossref","unstructured":"12. (a) R. Weidenhagen and U. Weeden, Ber., 1938, 71, 2347; (b) R. Weidenhagen and G. Train, Ber., 1942, 75, 1936.","DOI":"10.1002\/cber.19360690448"},{"key":"10.3987\/COM-05-10447-13","doi-asserted-by":"crossref","unstructured":"13. (a) P. K. Dubey and C. V. Ratnam, Proc. Indian Acad. Sci., 1977, 85, 204; (b) M. P. Singh and Y. Bathini, Heterocycles, 1993, 36, 971.","DOI":"10.1007\/BF03049482"},{"key":"10.3987\/COM-05-10447-14","unstructured":"14. We found that carrying out the reaction at a slightly elevated temperature (50\u00b0C) does accelerate the consumption of the starting material, however, it results in larger amounts of unidentified by-products compared to the reactions performed at room temperature."}],"container-title":["HETEROCYCLES"],"original-title":[],"language":"en","deposited":{"date-parts":[[2024,6,24]],"date-time":"2024-06-24T20:41:06Z","timestamp":1719261666000},"score":1,"resource":{"primary":{"URL":"https:\/\/triggered.stanford.clockss.org\/ServeContent?doi=10.3987%2Fcom-05-10447"},"secondary":[{"URL":"https:\/\/triggered.edinburgh.clockss.org\/ServeContent?doi=10.3987%2Fcom-05-10447","label":"edinburgh"}]},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2005]]},"references-count":14,"journal-issue":{"issue":"9","published-print":{"date-parts":[[2005]]}},"alternative-id":["COM-05-10447"],"URL":"https:\/\/doi.org\/10.3987\/com-05-10447","relation":{},"ISSN":["0385-5414"],"issn-type":[{"type":"print","value":"0385-5414"}],"subject":[],"published":{"date-parts":[[2005]]}}}