Vol.5, No 1, 2007 pp. 85 - 88
DOI 10.2298/FUPCT0701085D
UDC 537.569/.534.8

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SYNTHESIS OF NEW CONDENSED COUMARIN DERIVATIVES
Stojadin V. Dekić¹, Vidoslav S. Dekić¹, Branimirka Vučić², Biljana R. Dekić¹, Milan S. Dekić^3
1Department of Chemistry, Faculty of Sciences and Mathematics, K. Mitrovica, Serbia
²Business College, Blace, Serbia
³Department of Chemistry, Faculty of Sciences and Mathematics, Niš, Serbia

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Abstract. Reactions of 4-chloro-2-oxo-2H-chromene-3-carbonitrile (1) with 4-methyl-pyridin-2-ylamine (2) and 6-methoxy-benzothiazol-2-ylamine (3) in acetonitrile containing a catalytic amount of triethylamine gave the new coumarin derivatives 7-imino-10-methyl-7H-5-oxa-7a,12-diaza-benzo[a]anthracen-6-one (4) and 7-imino-10-methoxy-7H-5-oxa-12-thia-7a,13-diaza-indeno[1,2-b]phenanthren-6-one (5) in 52 and 39% yields, respectively. The novel compounds were subjected to acid hydrolysis giving the corresponding oxoderivatives 10-methyl-5-oxa-7a,12-diaza-benzo[a]anthracene-6,7-dione (6) and 10-methoxy-5-oxa-12-thia-7a,13-diaza-indeno[1,2-b]phenanthrene-6,7-dione (7) in 64 and 58% yields, respectively. The structural assignments of the synthesized compounds were based on elemental analyses, IR and proton NMR spectra.
Key words: synthesis, hydrolysis, structural determination

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SINTEZA NOVIH KONDENZOVANIH DERIVATA KUMARINA Reakcijama 4-hlor-2-okso-2H-hromen-3-karbonitrila (1) sa 4-metil-piridin-2-ilaminom (2) i 6-metoksi-benzotiazol-2-ilaminom (3) u acetonitrilu u prisustvu trietilamina kao katalizatora dobijeni su novi derivati kumarina 7-imino-10-metil-7H-5-oksa-7a,12-diaza-benzo[a]antracen-6-on (4) i 7-imino-10-metoksi-7H-5-oksa-12-tia-7a,13-diaza-indeno[1,2-b]fenantren-6-on (5) sa prinosima od 52%, odnosno 39%. Hidrolizom dobijenih jedinjenja u kiseloj sredini dobijeni su odgovarajući dioni 6-7 sa prinosima od 64%, odnosno 58%. Strukture sintetizovanih jedinjenja određene su na osnovu podataka dobijenih elementnom analizom, IC i protonskom NMR spektoskopijom