2-((Naphthalen-1-or-2-yl)methylene)cyclohexanone (1a,b) were synthesized through condensation of 1- and/or 2-naphthaldehyde with cyclohexanone. The cyclization of 1a,b with substituted hydrazines gave the corresponding hexahydroindazole derivatives 2a,b-6a,b. While on condensation with hydroxylamine hydrochloride and/or thiourea gave benzoisoxazole derivative 7a,b and quinazoline-2-thione derivative 8a,b. Also condensation of 1a,b with guanidine sulphate followed by chloroacetylation gave 10a,b which were condensed with ortho substituted aniline gave quinazoline derivatives 11a,b, 12a,b. Condensation of 1a,b with various active methylene compounds afforded the corresponding chromene derivatives 13a,b-15a,b. The antimicrobial activity of the newly synthesized compounds was done against different gram positive, gram negative bacteria and fungi species. Also the antioxidant activity of these compounds was evaluated.