Abstract Partially hydrogenated pyrido [2, 1-b][1, 3] oxazine, cyclopenta [d] pyrido [2, 1-b][1, 3] oxazine and pyrido [1, 2-a]-[3, 1] benzoxazine ring systems were easily formed in the reaction of 3-hydroxy-2-(2-hydroxy-1, 3-dioxo-2-indanyl)-2-alken-1-one derivatives with tosyl chloride and pyridine bases. A facile interconversion between pyridooxazines and the corresponding pyridinium salts was also realized.