Synthesis 2017; 49(07): 1597-1602
DOI: 10.1055/s-0036-1588375
paper
© Georg Thieme Verlag Stuttgart · New York

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

Hua-Shuai Gao
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: lmzhao@jsnu.edu.cn
,
Fei Dou
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: lmzhao@jsnu.edu.cn
,
Ai-Li Zhang
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: lmzhao@jsnu.edu.cn
,
Rui Sun
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: lmzhao@jsnu.edu.cn
,
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: lmzhao@jsnu.edu.cn
› Author Affiliations
Further Information

Publication History

Received: 07 October 2016

Accepted after revision: 21 November 2016

Publication Date:
09 December 2016 (online)


Abstract

The biologically important tetrahydro-1-benzazepine skeleton was conveniently constructed from N-arylated homoallylamines through H2SO4-mediated intramolecular cyclization. The advantages of this transformation include mild reaction conditions, experimental simplicity, its solvent- and metal-free, atom- and step-economical nature, and the use of a readily available, cheap, and nontoxic mediator.

Supporting Information