246546-72-5Relevant academic research and scientific papers
Fused quinoline heterocycles IV. First synthesis of four heterocyclic ring systems of 1H-5-thia-1,2,3,6-tetraazaacephenanthrylenes and 1H-5-thia-1,3,6-triazaacephenanthrylenes
Mekheimer, Ramadan A.,Ahmed, Essam Kh.,El-Fahham, Hassan A.,Kamel, Laila H.
, p. 49 - 63 (2001)
The synthesis of some novel fused tetracyclic compounds such as 1H-5-thia-1,2,3,6-tetraazaacephenanthrylenes and 1H-5-thia-1,3,6-triazaacephenanthrylenes containing quinoline ring system have been reported.
Fused quinoline heterocycles IV: First synthesis of four heterocyclic ring systems of 1H-5-thia-1,2,3,6-tetraazaacephenanthrylenes and 1H-5-thia-1,3,6-triazaacephenanthrylenes
Mekheimer,Ahmed,El-Fahham,Kamel
, p. 97 - 102 (2007/10/03)
Reaction of 4-alkylamino-2-chloroquinoline-3-carbonitriles 4a-e with an equimolecular amount of ethyl mercaptoacetate gave, in each case, the corresponding ethyl 4-alkylamino-3-aminothieno[2,3-b]quinoline-2-carboxylates 7a-e. Diazotization of 7a-e afforded the novel tetracyclic ring system ethyl 1-alkyl-1H-5-thia-1,2,3,6-tetraazaacephenanthrylene-4-carboxylates 8a-e. Refluxing 7a-e with an excess of triethyl orthoformate yields the new ethyl 1-alkyl-1H-5-thia-1,3,6-triazaacephenanthrylene-4-carboxylates 9a-e. Reacting 9b, c, as example, with an excess of cyclohexylamine (2a) in boiling DMF furnished the corresponding amides 10a, b in good yields.
Fused quinoline heterocycles I. First example of the 2,4-diazidoquinoline-3-carbonitrile and 1-aryl-1,5-dihydro-1,2,3,4,5,6-hexaazaacephenanthrylenes ring systems
Mekheimer, Ramadan A.
, p. 2183 - 2188 (2007/10/03)
4-Alkylamino-2-chloroquinoline-3-carbonitriles 2a-f react with hydrazine hydrate to give, in each case, the corresponding 3-amino-4-hydrazino-1H-pyrazolo[3,4-b]quinoline 7. Diazotization of 7 leads to the formation of 2,4-diazidoquinoline-3-carbonitrile 8, a new heterocyclic ring system. The azidoquinoline 8 can be converted to the corresponding aminoquinolines 14, and 15 and 16, by reaction with morpholine and sodium dithionite, respectively. On the other hand, 3-amino-4-arylamino-1H-pyrazolo[3,4-b]quinolines 4g-j were prepared by reaction of 4-arylamino-2-chloroquinoline-3-carbonitriles 2g-j with hydrazine hydrate at 50-60°C. Diazotization of 4g-j afforded the novel tetracyclic ring system 1-aryl-1,5-dihydro-1,2,3,4,5,6-hexaazaacephenanthrylenes 5g-j.
