ABSTRACT. An efficient and convenient procedure has been described for one-pot multi-component synthesis of tetrahydrobenzo [b]pyrans known as 2-amino-7,7-dimethyl-5-oxo-4-phenyl-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile which can be obtained from the reaction of substituted aromatic aldehydes, dimedone, malonitrile, in the presence of base such as potassium tertiary butoxide and THF in methanol as solvent at RT condition. All the compounds were examined by advanced spectroscopic data ( 1 H NMR, 13 C NMR and LCMS) and the structural determination was evaluated by elemental analysis. In addition to this, all the newly synthesized compounds were examined for their antibacterial activities and antifungal activity by disc diffusion method against the organism of Aspergillus niger and Candida ablicans L.