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5-Amino-2,3-dihydrophthalazine-1,4-dione (Luminol 1) reacted with some organophosphorus reagents such as phosphonium ylides, trialkyl phosphites, and tris(dialkylamino)phosphines to afford the corresponding olefinic products 5a-e, alkoxy-, and dialkylamino derivatives of Luminol 6a-e. 4-Thioxo-3,4-dihydrophthalazin-1(2H)-one derivative 7 was synthesized from the reaction of Luminol (1) with thiating Lawesson and Japanese reagents. Structures of the synthesized compounds were clarified based on their elemental and spectroscopic analyses. The synthesized compounds were evaluated for their antimicrobial activity against some bacterial and fungal strains.