Sk Jubayar Ahashan, Kousik Maji, Syed Ramizul Kabir, Jyotirmayee Dash
a Lawesson's reagent-mediated thiocarbonyl Cloke-Wilson rearrangement of spiro donor-acceptor cyclopropyl oxindoles, followed by oxidative aromatization under open-air conditions. The reaction proceeds smoothly under mild conditions, tolerates a range of aryl substrates, and can be performed on a synthetically relevant scale. Control experiments and DFT studies indicate a stepwise rearrangement pathway in which aerial oxygen promotes a barrier-less aromatization driven by aromatic stabilization. This work demonstrates the versatility of donor-acceptor cyclopropanes as efficient building blocks for the construction of sulfur-containing fused heteroaromatic frameworks.