Phosphoryl chloride-mediated solvent-free synthesis of N-aryl-substituted azacycles from arylamines and cyclic ethers |
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| Affiliation: | 1. Department of Nuclear Medicine, Molecular Imaging & Therapeutic Medicine Research Center, Chonbuk National University Medical School and Hospital, Jeonju 54907, Republic of Korea;2. Research Institute of Clinical Medicine of Chonbuk National University-Biomedical Research Institute of Chonbuk National University Hospital, Jeonju 54907, Republic of Korea;1. Key Laboratory of Functional Small Organic Molecule, Ministry of Education and College of Chemistry & Chemical Engineering, Jiangxi Normal University, Nanchang 330022, PR China;2. College of Ecology and Resources Engineering, Wuyi University, Wuyishan City 354300, PR China;1. State Key Laboratory for Oxo Synthesis and Selective Oxidation, Suzhou Research Institute of LICP, Center for Excellence in Molecular Synthesis, Lanzhou Institute of Chemical Physics (LICP), Chinese Academy of Sciences, Lanzhou 730000, PR China;2. University of Chinese Academy of Sciences, Beijing 100049, PR China;3. College of Chemistry and Chemical Engineering, Hunan Institute of Engineering, Xiangtan 411104, PR China;4. College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou 450001, PR China;1. Inorganic Materials and Catalysis Division, CSIR-Central Salt and Marine Chemicals Research Institute (CSIR-CSMCRI), Council of Scientific & Industrial Research (CSIR), G. B. Marg, Bhavnagar, 364002 Gujarat, India;2. Academy of Scientific and Innovative Research (AcSIR), CSIR-CSMCRI, Bhavnagar, 364002 Gujarat, India |
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| Abstract: | A solvent- and metal-free protocol for preparation of N-aryl substituted azacycles from arylamines and cyclic ethers is described. In this method, the combination of POCl3 and DBU is crucial for conversion of arylamines and cyclic ethers to five- and six-membered azacycles. Without solvent, a variety of N-aryl-substituted, five-membered azacycles (pyrrolidines, 2-methylpyrrolidines, and piperidine) and six-membered azacycles (isoindolines and tetrahydroisoquinolines) are synthesized in high yields. This green method provides a sustainable and efficient approach for the preparation of azacycles from various cyclic ethers. |
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| Keywords: | Azacycles Heterocycle Cyclic ether Metal-free reaction |
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