Behaviour and Reactions of Some Quinolinone Derivatives
Mohamed Mahmoud Mohamed Hassan;
Abstract
The present work deals with reactions and behaviour of 4- hydroxy-8-methyl-2(1H)quinolinone (1), which was subjected to several and different chemical transformations aiming to synthesize novel quinoline derivatives, which may have important biological activity.
The compound 1 reacted with phosphorus oxychloride and phosphorus pentachloride to give 2,4-dich.loro-8-methylquinoline (2), which on hydrolysis with diluted hydrochloric acid furnished
4-chloro-8-methyl-2(1H)quinolinone (4). Similarly, reaction of 1 with phosphorus pentabromide afforded 2,4-dibromo-8- methylquinoline (3), which also hydrolyzed to give 4-bromo-8- methyl-2(1H)quinolinone (5).
Reaction of compound 2 with sodium azide was studied under different reaction conditions. Thus, when compound 2 was reacted with sodium azide, in DMF or N-methyl-2-pyrrolidinone (NMP), 4-azido-2-chloro-8-methylquinoline (6) was afforded. 2- Azido-4-chloro-8-methylquinoline (7), the isomer of 6, which was found to be present mainly as 5-chloro-9-methyltetrazolo[l ,5- a]quinoline, was achieved by azidation of 2, in ethanol, using trifluoroacetic acid or p-toluenesulphonic acid as a catalyst. Reaction of either 6 or 7 with excess sodium azide, in ethanol containing an acid catalyst, or DMF, furnished 5-Azido-9- methyltetrazolo[1,5-a]quinoline (8). The azidotetrazoloquinoline
8 was also obtained, but in a poorer yield, directly from exhaustive nucleophilic azidation of compound 2.
The compound 1 reacted with phosphorus oxychloride and phosphorus pentachloride to give 2,4-dich.loro-8-methylquinoline (2), which on hydrolysis with diluted hydrochloric acid furnished
4-chloro-8-methyl-2(1H)quinolinone (4). Similarly, reaction of 1 with phosphorus pentabromide afforded 2,4-dibromo-8- methylquinoline (3), which also hydrolyzed to give 4-bromo-8- methyl-2(1H)quinolinone (5).
Reaction of compound 2 with sodium azide was studied under different reaction conditions. Thus, when compound 2 was reacted with sodium azide, in DMF or N-methyl-2-pyrrolidinone (NMP), 4-azido-2-chloro-8-methylquinoline (6) was afforded. 2- Azido-4-chloro-8-methylquinoline (7), the isomer of 6, which was found to be present mainly as 5-chloro-9-methyltetrazolo[l ,5- a]quinoline, was achieved by azidation of 2, in ethanol, using trifluoroacetic acid or p-toluenesulphonic acid as a catalyst. Reaction of either 6 or 7 with excess sodium azide, in ethanol containing an acid catalyst, or DMF, furnished 5-Azido-9- methyltetrazolo[1,5-a]quinoline (8). The azidotetrazoloquinoline
8 was also obtained, but in a poorer yield, directly from exhaustive nucleophilic azidation of compound 2.
Other data
| Title | Behaviour and Reactions of Some Quinolinone Derivatives | Other Titles | سلوك وتفاعلات بعض مشتقات الكينولينون | Authors | Mohamed Mahmoud Mohamed Hassan | Issue Date | 1999 |
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