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Synthesis 2001; 2001(1): 0097-0102
DOI: 10.1055/s-2001-9750
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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

Ramadan Ahmed Mekheimer* , Essam Khalaf Ahmed, Hassan Attia El-Fahham, Laila Hanafy Kamel
  • *Department of Chemistry, Faculty of Science, El-Minia University, El-Minia 61519, AR Egypt; E-mail: r.mekh§scc-alph.mini.eun.eg
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Publikationsdatum:
31. Dezember 2001 (online)

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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-aminothiono[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.

synthesis - thieno[2,3-b]quinolines - fused tetracyclic compounds