A green chemical approach for silicon containing 4-iodo-3-trimethylsilylpyrano[4,3-b]quinolines, 8 is established through DIH mediated regioselective electrophilic iodocyclisation of unactivated internal alkynes, 7 with high yields. An excellent 6-endo-dig regioselectivity owing to the behaviour of DIH in different solvents was observed. [Figure not available: see fulltext.]. © 2020, Springer Nature B.V.