Solvent free synthesis of 3-Aryl-1-(2-aryl-1H-indol-3-yl)prop-2-en-1-one has been successfully accomplished in high yields and lesser time by using green chemistry techniques(Grindstone chemistry and microwave irradiation). 3- Acetyl-2-phenyl indoles on treatment with either acidic or basic catalyst generate the corresponding enolates which reacts with aryl aldehydes affording the desired title products. All the synthesized compounds have been characterized by elemental analyses and spectral data (IR,1HNMR and Mass). They have also been screened for their antibacterial and anti spermicidal activities and some of them have shown promising results against Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa.