The aim of the present work is to design and synthesize some new nitrogenous naphthoquinone, -lapachone analogues, binary, fused, and spiro ring compounds moiety which incorporate heterocyclic moieties of anticipated biological value. Thus, in light of the aforementioned importance of the lawsone compounds, the present work is planned to investigate the reactivity of lawsone and its annulated compounds towards several reagents and conditions. The synthetic compounds have Furthermore, geometrical studies and biological applications of the newly synthesized compounds were implemented. Accordingly, the thesis is subdivided into three parts. Part 1: Chemical reactivity studiesThis part is subdivided into three sectionsSection one: Adaptable Access for Naphthoquinone AnnulationsSection two: Concise Synthesis of New -Lapachone AnaloguesSection three: Synthesis of Some Novel Spiro Lawsone-Ring Skeletons Spiro CompoundsPart II: Geometrical Calculation and Molecular ModelingPartIII: Biological activity 1- Antioxidant activity for ABTS 2- Antitumor activity 3- In-vitro cytotoxic activities