A one‐pot, facile method has been established for the preparation of 1H‐1,2,3‐triazolyl 1,2‐dihydropyridyl derivatives 6 a‐y. The ring opening of the chromone and cyclo addition are the notable reactions to achieve the target compounds 6 a‐y. All the compounds were screened for their antiproliferative, free radical scavenging (DPPH, ABTS.+), α‐glucosidase inhibitory and anti‐inflammatory activities. The bioactivity profile revealed that the compounds 6 x‐y were shown potent antiproliferative activity against HeLa cell line, while compounds 6 e‐h and 6 w identified as potent ABTS+. and 6 n identified as potent DPPH free radical scavenger. Compounds 6 h‐i, 6 p‐r, 6 u and 6 w denoted promising anti‐inflammatory activity.