title: One-step cyclization: synthesis of N-heteroalkyl-N'-tosylpiperazines.
abstract: Piperazine derivatives are important intermediates in organic synthesis and useful building blocks in pharmaceutical and fine chemical industries. Currently available synthetic routes for these heterocyclic compounds have limited scope owing to the harsh reaction conditions, low yields, and multistep process. Herein, we reported a practical method for synthesis of alkyl-, alcohol-, amine-, and ester-extended tosylpiperazines under mild conditions with moderate to high yields. This protocol exhibits potential applicability in the synthesis of pharmaceuticals and natural products because of the operational simplicity and the conveniently available reactants. On the basis of the experimental and theoretical results, a plausible mechanism of aliphatic nucleophilic substitution (S(N)) in the cyclization has been postulated and evidence for the formation of a six-membered ring has also been confirmed by means of density functional theory (DFT) calculations.
authors: College of Food Science and Biotechnology, Zhejiang Gongshang University, Hangzhou 310035, P. R. China. huangjy@mail.zjgsu.edu.cn
authors: Jianying
authors: J
authors: Huang
authors: Weiyuan
authors: W
authors: Xu
authors: Hujun
authors: H
authors: Xie
authors: Shijun
authors: S
authors: Li
mesh_terms: D003500:Cyclization; D015394:Molecular Structure; D010879:Piperazines / Q000138:chemical synthesis* / Q000737:chemistry; D011789:Quantum Theory; D013237:Stereoisomerism; D014105:Tosyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D010879:Piperazines; D014105:Tosyl Compounds