The synthesis of 7-amino-2-methylquinoline-5-8-dione (17) and 7-amino-3-methylquinoline-5,8-dione (157) are described.7-Amino-3-methylquinoline-5,8-dione (157) was prepared via alkaline hydrolysis of 7-acetamido-3-methylquinoline5,8-dione (149). 7-Acetamido-3-methylquinoline-5,8-dione (149) was prepared via the Diels-Alder reaction of 2-acetamido-6-bromo-1,4-benzoquinone (6) and 2-methyl-2propenal dimethylhydrazone (110).7-Amino-2-methylquinoline-5,8-dione (17) was prepared by the acid hydrolysis of 7-(triphenylphosphineimino)-2methylquinoline-5,8-dione (16). 7-(Triphenylphosphineimino)2-methylquinoline-5,8-dione (16) was prepared by tie treatment of 7-azido-2-methylquinoline-5,3-dione (15) with triphenylphosphine. 7-Azido-2-methylquinoline-5,8-dione (15) was prepared by treating 7-bromo-2-methylquinoline-5,8-dione (14) with sodium azide. The structures of the new compounds 15, 16, 17,149 and 157 were confirmed using MP, NMR, IR, MS and HRMS data. NMR, IR and MS data for known compounds 10, 11, 12, 13 and 14 are included for future reference.Ball State UniversityMuncie, IN 47306
| Identifer | oai:union.ndltd.org:BSU/oai:cardinalscholar.bsu.edu:handle/183349 |
| Date | 03 June 2011 |
| Creators | Horn, Mark A. |
| Contributors | Behforouz, Mohammad |
| Source Sets | Ball State University |
| Detected Language | English |
| Format | x, 107 leaves : ill. ; 28 cm. |
| Source | Virtual Press |
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