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H2SO4-Mediated Intramolecular Cyclization of N-Arylated Homoallylamines: A Solvent-Free, Atom- and Step-Economical Synthesis of Tetrahydro-1-benzazepines

Hua-Shuai Gao, Fei Dou, Ai-Li Zhang, Rui Sun, Li-Ming Zhao*

*School of Chemistry and Chemical Engineering, and Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou 221116, Jiangsu, P. R. of China, Email: lmzhaojsnu.edu.cn

H.-S. Gao, F. Dou, A.-L. Zhang, R. Sun, L.-M. Zhao, Synthesis, 2017, 49, 1597-1602.

DOI: 10.1055/s-0036-1588375 (free Supporting Information)


Abstract

A H2SO4-mediated intramolecular cyclization enables the preparation of biologically important tetrahydro-1-benzazepines from N-arylated homoallylamines. This solvent- and metal-free, atom- and step-economical transformation offers mild reaction conditions, experimental simplicity, and the use of a readily available, cheap, and nontoxic mediator.

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Key Words

cyclization, alkylation, benzo-fused N-heterocycles, solvent-free, metal-free, sulfuric acid


ID: J66-Y2017