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Paper | Regular issue | Vol 78, No. 2, 2009, pp.337-345
Published online, 25th September, 2008
DOI: 10.3987/COM-08-11481
Synthesis of Tetra- and Penta-heterocyclic Compounds Incorporated Isoquinoline Moiety

Tayseer A. Abdallah,* Hamdi M. Hassaneen, and Hayam A. Abdelhadi

*Department of Chemistry, Faculty of Science, Cairo University, Giza 12613, Egypt


7-Amino-2,3-dimethoxy-9-phenyl-5,6,9,6a-tetrahydropyridino[2,1-a]isoquinoline-8,10-dicarbonitrile 5 was prepared via Michael addition reaction of benzylidenemalononitrile 2 with isoquinoline-1-carbonitrile 1. Reaction of 5 with triethyl orthoformate and formamide led to the formation of the corresponding 4-ethoxymethylene and 4-aminopyrimidine derivatives of benzo[a]quinolizines 6 and 7, respectively. Compound 6 reacted with hydrazine to give imino-amino compound 8. The latter compound reacted with formic acid, triethy1 orthoformate, acetic anhydride or benzoy1 chloride to give the triazolopyrimidine derivatives 9, 10 and 11, respectively. Compound 8 reacted with hydrazonoy1 halides 12, 13 and diethy1 oxalate to give triazinopyrimidine and triazolopyrimidine derivatives 16, 17 and 20, respectively.