高等学校化学学报2025，Vol.46Issue(5)：63-74,12.DOI:10.7503/cjcu20240547
2-苯基-3-氨基氮杂环丁烷开环形成噻唑或噁唑的机理研究
Ring-opening Mechanism of 2-Phenyl-3-amineazetidine to Form Thiazole or Oxazole
摘要
Abstract
Based on the density functional theory(DFT),the Minnesota functional M06-2X method was employed to study the ring-opening reaction mechanism of(2S,3S)-2-phenyl-1-[(S)-1-phenylethyl]azetidin-3-amine reacting with phenylisothiocyanate or phenylisocyanate.The amine reacting with phenylisothiocyanate generates an interme-diate,which then undergoes proton transfer.Subsequently,the sulfur atom conducts a nucleophilic attack on the C2 position of the four-membered ring to give dihydrothiazole after isomerization from a five-membered ring.The amine reacting with phenylisocyanate forms urea.Protic acid or copper trifluoromethanesulfonate is required when the four-membered ring of the urea undergoes a ring-opening reaction.关键词
3-氨基氮杂环丁烷/开环反应/密度泛函理论/反应机理Key words
3-Aminoazetidine/Ring opening reaction/Density functional theory/Reaction mechanism分类
化学引用本文复制引用
顼兴宇,解晓明,邱萍..2-苯基-3-氨基氮杂环丁烷开环形成噻唑或噁唑的机理研究[J].高等学校化学学报,2025,46(5):63-74,12.基金项目
山西省高等学校科技创新项目(批准号:2021L456)资助. Supported by the Scientific and Technological Innovation Programs of Higher Education Institutions in Shanxi Province,China(No.2021L456). （批准号:2021L456）
