In this manuscript we report the synthesis of 3‐amido‐benzo[b]silines thanks to a 2‐step strategy involving a 3‐component silylformylation of ynamides followed by a Friedel‐Crafts cyclization/ isomerizing dehydration domino sequence. This reaction is tolerant to various structural variations and has allowed us to synthesize a library of diversely substituted silacycles with yields from 28 to 85%. We also studied the fluorescence properties of these compounds which show structural similarities with recognized probes such as Si‐Rhodamine for example.