Syntheses of 3-aminoquinoline-2,4(1H,3H)-diones

Kafka, Stanislav; Klásek, Antonín; Polis, Jiří; Košmrlj, Janez

dc.title	Syntheses of 3-aminoquinoline-2,4(1H,3H)-diones	en
dc.contributor.author	Kafka, Stanislav
dc.contributor.author	Klásek, Antonín
dc.contributor.author	Polis, Jiří
dc.contributor.author	Košmrlj, Janez
dc.relation.ispartof	Heterocycles
dc.identifier.issn	0385-5414 Scopus Sources, Sherpa/RoMEO, JCR
dc.date.issued	2002
utb.relation.volume	57
utb.relation.issue	9
dc.citation.spage	1659
dc.citation.epage	1682
dc.type	article
dc.language.iso	en
dc.publisher	Pergamon Elsevier Science Ltd.	en
dc.identifier.doi	10.3987/COM-02-9522
dc.relation.uri	http://www.heterocycles.jp/newlibrary/libraries/search
dc.subject	aminolýza	cs
dc.subject	amonolýza	cs
dc.subject	azidy	cs
dc.subject	redukce	cs
dc.subject	aminolysis	en
dc.subject	ammonolysis	en
dc.subject	azides	en
dc.subject	reduction	en
dc.description.abstract	3-Chloro- and 3-bromoquinoline-2,4(1H,3H)-diones react with excess of primary alkyl or arylamines in dimethylformamide to the corresponding 3-alkyl- or 3-arylamino derivatives. The compounds with the primary amino group at the 3 position were best prepared by reaction of 3-chloroquinoline-2,4(1H,3H)-diones with in situ generated ammonia under anhydrous conditions. An alternative approach to the primary amines via reduction of 3-azidoquinoline-2,4(1H,3H)-diones was investigated. The reduction of 3-azidoquinoline-2,4(1H,3H)-diones with zinc in acetic acid gave moderate to good yields of the desired products, while the reaction with triphenylphosphane afforded exclusively 4-hydroxyquinoline-2(1H)-ones.	en
utb.faculty	Faculty of Technology
dc.identifier.uri	http://hdl.handle.net/10563/1000102
utb.identifier.rivid	RIV/70883521:28110/02:63500546
utb.identifier.obdid	11052428
utb.identifier.scopus	2-s2.0-0036731722
utb.identifier.wok	000178032100009
utb.source	j-riv
utb.contributor.internalauthor	Kafka, Stanislav
utb.contributor.internalauthor	Klásek, Antonín
utb.contributor.internalauthor	Polis, Jiří
utb.fulltext.affiliation	Stanislav Kafka,a Antonín Klásek,a,* Jiří Polis,a and Janez Košmrlj b a Faculty of Technology, Tomas Bata University in Zlín, 762 72 Zlín, Czech Republic (e-mail: [email protected]) and b Faculty of Chemistry and Chemical Technology, University of Ljubljana, 1000 Ljubljana, Slovenia
utb.fulltext.dates	-
utb.fulltext.references	1. S. Kafka, M. Kovář, A. Klásek, and T. Kappe, J. Heterocycl. Chem., 1996, 33, 1977. 2. A. Klásek and S. Kafka, J. Heterocycl. Chem., 1998, 35, 307. 3. A. Klásek, K. Kořistek, J. Polis, and J. Košmrlj, Heterocycles, 1998, 48, 2309. 4. A. Klásek, K. Kořistek, J. Polis, and J. Košmrlj, Tetrahedron, 2000, 56, 1551. 5. S. Kafka, A. Klásek, and J. Košmrlj, J. Org. Chem., 2001, 66, 6394. 6. C. Podesva, K. Vagi, and C. Solomon, Can. J. Chem., 1968, 46, 2263. 7. W. Stadlbauer, H. Lutschounig, G. Schindler, T. Witoszynskij, and T. Kappe, J. Heterocycl. Chem., 1992, 29, 1535. 8. M. Harfenist and E. Magnien, J. Org. Chem., 1963, 28, 538; R. E. Bowman, T. F. Grey, D. Huckle, I. M. Lockhart, and M. Wright, J. Chem. Soc., 1964, 3350. 9. W. Stadlbauer, R. Laschober, H. Lutschounig, G. Schindler, and T. Kappe, Monatsh. Chem., 1992, 123, 617. 10. A. Klásek, S. Kafka, and T. Kappe, Collect. Czech. Chem. Commun., 1995, 60, 2137. 11. I. V. Ukrainets, S. G. Taran, O. A. Evtifeeva, O. V. Gorokhova, N. I. Filimonova, and A. V. Turov, Khim. Geterotsikl. Soedin., 1995, 204. 12. E. Malle, W. Stadlbauer, G. Ostermann, B. Hofmann, H. J. Leis, and G. M. Kostner, Eur. J. Med. Chem. Chim. Ther., 1990, 25, 137. 13. R. Laschober and W. Stadlbauer, Liebigs Ann. Chem., 1990, 1083. 14. H. Staudinger and E. Hauser, Helv. Chim. Acta, 1921, 4, 861; H. Staudinger and J. Meyer, Helv. Chim. Acta, 1919, 2, 635. 15. For a rewiev on Staudinger reaction, see: Y. G. Gololobov and L. F. Kasukhin, Tetrahedron, 1992, 48, 1353. 16. A. W. Johnson, 'Ylides and Imines of Phosphorus', John Wiley & Sons, New York, 1993, p. 104. 17. L. Benati, R. Leardini, M. Minozzi, D. Nanni, P. Spagnolo, S. Strazzari, G. Zanardi, and G. Calestani, Tetrahedron, 2002, 58, 3485 and references cited therein. 18. I. V. Ukrainets, S. G. Taran, O. A. Evtifeeva, O. V. Gorokhova, P. A. Bezuglyi, A. V. Turov, L. N. Voronina, and N. I. Filimonova, Khim. Geterotsikl. Soedin., 1994, 673. 19. P. Baumgarten and W. Kärgel, Ber., 1927, 60, 832. 20. W. Stadlbauer, O. Schmut, and T. Kappe, Monatsh. Chem., 1980, 111, 1005. 21. L. F. Wiggins, J. W. James, and R. W. Temple, U. S. Patent 3,133,928, 1964 (Chem. Abstr., 1964, 61, 6997).
utb.fulltext.sponsorship	This study was supported by the Ministry of Education, Youth and Sports of the Czech Republic and the Ministry of Education, Science and Sport, Republic of Slovenia (Grant No. P0-0503-0103). The authors thank to Mrs. H. Geržová (Faculty of Technology, Tomas Bata University in Zlin, Czech Republic) for technical help, and Drs. Bogdan Kralj and Dušan Žigon (Mass Spectrometry Center, Jožef Stefan Institute Ljubljana, Slovenia) for mass spectral measurements.
utb.fulltext.projects	P0-0503-0103