The naphthalene framework has been found in a wide variety of commercially important compounds such as pharmaceutical and agricultural agents. One of the interests in our lab is to synthesize new compounds which are based on 2-tetralone and 2-naphthol. The naphthalene skeletal framework served as a template for the three novel synthetic compound classes reported in this thesis. Chapter 1 of this thesis described the 2,3-dihydro-1'H'-naphtho[' 2,1-b']pyran scaffold derived from 2-tetralone and 2-naphthol analogs. The final compounds 2,2-disubstituted-2,3-dihydro-1'H'-napht ho[' 2,1-b']pyrans were successfully synthesized in good to excellent yields from 2-tetralone analogs and 2,2-disubstituted-3-hydroxypropanals. This methodology involves a facile acid-catalyzed aldol condensation and cyclization, followed by aromatization. Fifteen examples were prepared to demonstrate the generality of the reaction. In another endeavor, a novel multi-component synthesis of 3-dialkylamino-2,2-dialkyl-2,3-dihydro-1 ' H'-naphtho['2,1-b']pyrans was developed in a one-pot microwave-assisted procedure from 2-naphthol, cyclic secondary amines and 2,2-disubstituted-3-hydroxypropanals. Several side products such as 2-naphthol Mannich base, 2,3-dihydro-2,2-dimethyl-1'H'-naphtho[' 2,1-b']pyran-3-ol, and 1-((2-hydroxynaphthalen-1-yl)methyl)naph thalen-2-ol were also obtained. The investigation revealed that 2,2-disubstituted-3-hydroxypropanals underwent retro-aldol condensation into formaldehyde and _,_-disubstituted acetaldehyde, this was followed by the reaction of 2-naphthol, in-situ generated formaldehyde and the secondary amine to form a Mannich bases and an enamine intermediate formed by the secondary amine and in-situ generated 2,2-disubstituted acetaldehyde. Subsequently, the Mannich base underwent deamination to produce a quinone-methide intermediate which reacted with the enamine via pericyclic cycloaddtion to form the desired products in low to moderate yields. This proposition also explains the formation of isolated side products. Chapter 2 of this thesis deals with synthesis of novel bis-Mannich bases of 2-naphthols derived from aromatic aldehydes and diamines such as piperazine and 'N,N'-dialkylethylenediamine. Mannich bases of 2-naphthol have the ability to chelate strongly to metal ions. Hence, they have great potential to be used as chiral catalysts, metallo-enzyme inhibitors and/or scavenger of heavy metal poisons. An efficient and expeditious microwave assisted-synthesis of 'bis'-Mannich bases of 2-naphthols was developed under solvent-free conditions. With appropriate molar ratios of aromatic aldehydes, piperazine and 2-naphthol, 'N,N'' -bis(ary1-2-hydroxynaphthylmethyl)pipera zines were successfully prepared using three different conditions, namely microwave-assisted solvent-free conditions, conventional reflux in ethanol and room temperature standing in ethanol for various lengths of time.
