Synthesis of thieno[2,3- b ]indoles by Cloke–Wilson rearrangement of spiro donor–acceptor cyclopropanes
Abstract
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.
Fields of Study & Subjects
Synthesis and Reactivity of Sulfur-Containing Compounds
Sulfur-Based Synthesis Techniques
Synthesis of heterocyclic compounds
Publication details
- Journal / source
- Chemical Communications
- Publisher
- Royal Society of Chemistry (RSC)
- Volume
- 62
- Issue
- 12
- Pages
- 3861–3865
- Publication date
- 1 January 2026
- Language
- EN