A bo u E lfatooh G. H am m am 3, N agla A. A bd E l-hafeza, W anda H. M idurab, and M arian M ikołajczykb a N ational R esearch C enter, D ep artm en t o f O rganic Chem istry, D o k k i, G iza, Egypt b C entre o f M olecular and M acrom olecular Studies, Polish A ca d em y o f Sciences, 9 0 -3 6 3 L odz, S ienk iew icza 112, Poland Reprint requests to Prof. M. M ikolajczyk. Fax: + 4 8 (0 )4 2 6 8 4 -7 1 -2 6 . E-mail: m arm ikol@ bilbo.cbm m .lodz.pl Z. Naturforsch. 55b, 4 1 7 -4 2 4 (2000); received N o v em b er 2, 1999 B enzothiep in o-pyrid in es, B icyclic Sulfones, H eterocyclization s Several new pyridines, pyridones and pyrans fused to b en zo th iep in e or b e n zo h ep ten e ring were synthesized as potential anticancer and an ti-H IV agents. T he fused-ring pyridines 6. 7 and 17-19 were obtained via the reaction o f the seven -m em b ered ring k eto n es 1, 2 and 3 with an arylidene-m alononitrile and by treatm ent o f the y lid en em alon on itriles 14, 15 and 16 with arom atic aldehydes, respectively. The correspon ding pyridon es 11, 12 and 13 w ere pre pared from the k eton es 1, 2 and 3 and arylm eth ylen ecyan oacetam id e. The synthesis o f the fused-ring pyranes 8 and 9 involved the co n d en sation o f the k eto n es 4 and 5 with m alononitrile under basic conditions. The rearrangem ent o f 8 under acidic con d ition s gave the tetrahydropyridine 10. The pyran 20 was ob tain ed from 15 and b en zaldehyd e. The screening tests sh ow ed that m any o f the com poun ds ob tain ed exhibit g o o d anticancer activity com parable to 5-fluorodeoxyurid in e used as reference com p ou n d and m od erate an ti-H IV activity in co m parison with AZT.