4-Methyl-2H-naphtho[1,2-b]pyran-2-one (I), 2-oxo-2H-naphtho[1,2-b]pyran-4-acetic acid (II), 1-methyl-3H-naphtho[2,1-b]pyran-3-one (III) and 3-oxo-3H-naphtho [2,1-b]pyran-1-acetic acid (IV), have been synthesized. Compound (I) and (II) condensed with aromatic aldehydes to give 2-naphthalene acrylic acid (Va- d), and 4-styryl pyranones (VIa-e) derivatives. Va and/or Vd reacted with maleic anhydride under Diels-Alder condition to give 2- naphthalenyl cyclohex-4-ene 1,2,3-tricarboxylic acid derivatives (VIIIa & b), decarboxylation of VIIa gave 2-naphthalenyl cyclohex-2-ene-1-carboxylic acid derivative (VIII). The 4-styryl pyranones derivatives (VId & e) reacted with maleic anhydride to give benzo[d]naphtho[1,2-b]pyranone derivatives (Xa & b). Compound (Xa) condensed with hydrazines, amines and thiourea to give naphthalenyl-N-substituted cyclohexene carboxamide derivatives (XIa-d), while (Xa) reacted with Grignard reagents to give naphthalenyl cyclohexenyl aryl ketone derivatives (XIIa-c), also (Xa) reacted with benzene under Friedel-Crafts condition to give (XIIa).
H M BAKEER ,S EL NAGDY ,A Y SOLIMAN ,A M YOUSSEF ,
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