Both oxazines and coumarins are the important class of heterocyclic compounds by virtue of its medicinal, pharmaceutical and therapeutic properties. Coumarin which is an important chemical entity with fused form of benzene and pyrone, 1,3 oxazine has its own significance when it is in individual aliphatic ring form or fused with other chemical entity. This work describes the formation of oxazine bridge between coumarin moiety and a pyridine ring followed by its docking study against two cancer related target proteins viz.rho associated protein kinase 1(PDBID : 3TWJ) for breast cancer and aryl amine N-transferase 2(PDBID : 2PFR) for colon cancer. All the synthesized compound sexhibited good resistance to the target enzymes as indicated by better glide score as compared to standard reference drugs. The compounds were able to interact strongly with active sites pocket residues resulting in the formation of strong favorable molecular interactions. 8-methyl amino-7-bromo coumarin was prepared by reducing 8-formyl -7-bromo coumarin in methanolic ammonia under hydrogen pressure. Condensing ethyl esters of α, β and γ picolinic acids with 8-methyl amino-7-bromocoumarin followed by cyclization in presence of P2O5 resulted a new series of 1,3 oxazines.