CAS OpenIR
Highly Efficient Conversion of Ketazines to Pyrazoline Derivatives Catalyzed by FeCl3
Xia, Yangfeng1,2; Zhang, Xing3; Liu, Long1; Sun, Haiyun3; Zhao, Guoying1; Zhang, Yanqiang4,5
2020-10-21
Source PublicationINDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH
ISSN0888-5885
Volume59Issue:42Pages:18748-18755
AbstractPyrazoline derivatives as valuable five-membered heterocyclic compounds could be readily prepared through the intramolecular cyclization of ketazines. In this paper, transition metals (Zn2+, Cu2+, Cr3+, Mn2+, Co2+, Ni2+, and Fe3+) were applied for the catalytic synthesis of 3,5,5-trimethyl-2-pyrazoline, and FeCl3 showed the best catalytic performance with 95% conversion and 99% selectivity. Substrate screening exhibited that the steric hindrance of ketazines is a key factor on the conversions of R-substituted pyrazolines, following the order of R as methyl (95%) > ethyl (83%) > propyl (68%) > butyl (55%). Moreover, the mechanism of the cyclization of ketazines catalyzed by FeCl3 is calculated by density functional theory. The energetic profile shows that the cyclization reaction consists of two steps and FeCl3 can efficiently reduce their barrier energies. This work provides a feasible method for the preparation of pyrazoline derivatives using inexpensive, less toxic, and environmentally friendly FeCl3 as a catalyst.
DOI10.1021/acs.iecr.0c04032
Language英语
WOS KeywordTRANSITION-METAL SALTS ; ALPHA,BETA-UNSATURATED KETONES ; POLYMERIZATION ; DENSITY
Funding ProjectNational Natural Science Foundation of China[21878278] ; National Natural Science Foundation of China[21676281]
WOS Research AreaEngineering
WOS SubjectEngineering, Chemical
Funding OrganizationNational Natural Science Foundation of China
WOS IDWOS:000584932100003
PublisherAMER CHEMICAL SOC
Citation statistics
Document Type期刊论文
Identifierhttp://ir.ipe.ac.cn/handle/122111/42726
Collection中国科学院过程工程研究所
Corresponding AuthorSun, Haiyun; Zhang, Yanqiang
Affiliation1.Chinese Acad Sci, Beijing Key Lab Ion Liquids Clean Proc, Inst Proc Engn, Beijing 100049, Peoples R China
2.Univ Chinese Acad Sci, Sch Chem Engn, Beijing 100049, Peoples R China
3.Beijing Inst Aerosp Testing Technol, Beijing Key Lab Res & Applicat Aerosp Green Prope, Beijing 10074, Peoples R China
4.Chinese Acad Sci, Key Lab Sci & Technol Particle Mat, Inst Proc Engn, Beijing 100049, Peoples R China
5.Zhengzhou Inst Emerging Ind Technol, Zhengzhou 450000, Peoples R China
Recommended Citation
GB/T 7714
Xia, Yangfeng,Zhang, Xing,Liu, Long,et al. Highly Efficient Conversion of Ketazines to Pyrazoline Derivatives Catalyzed by FeCl3[J]. INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH,2020,59(42):18748-18755.
APA Xia, Yangfeng,Zhang, Xing,Liu, Long,Sun, Haiyun,Zhao, Guoying,&Zhang, Yanqiang.(2020).Highly Efficient Conversion of Ketazines to Pyrazoline Derivatives Catalyzed by FeCl3.INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH,59(42),18748-18755.
MLA Xia, Yangfeng,et al."Highly Efficient Conversion of Ketazines to Pyrazoline Derivatives Catalyzed by FeCl3".INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH 59.42(2020):18748-18755.
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