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Transition Metal-Free One-Pot Synthesis of Fused 1,4-Thiazepin-5(4H)‑ones and Theoretical Study of the S–N Type Smiles Rearrangement Process

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posted on 05.09.2014, 00:00 by Bingchuan Yang, Xiaochen Tan, Ruiying Guo, Shunwei Chen, Zeyuan Zhang, Xianglong Chu, Caixia Xie, Dongju Zhang, Chen Ma
A series of 1,4-thiazepin-5­(4H)-one derivatives were synthesized via a transition metal-free one-pot Smiles rearrangement process at room temperature. Regioselective seven-membered heterocycles were constructed in good to excellent yields. To gain an in-depth understanding of the S–N type Smiles rearrangement mechanism, a theoretical study was also performed by quantum chemistry calculations.