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Iron-catalyzed cycloaddition reaction of diynes and cyanamides at room temperature.
J Org Chem. 2013 Apr 05; 78(7):3065-72.JO

Abstract

An iron-catalyzed [2 + 2 + 2] cycloaddition reaction of diynes and cyanamides at room temperature is reported. Highly substituted 2-aminopyridines were obtained in good to excellent yields with high regioselectivity. Insights toward the reaction process were investigated through in situ IR spectra and control experiments. In this iron-catalyzed cycloaddition reaction, the active iron species was generated only in the presence of both alkynes and nitriles. The lower reaction temperature, broad substrates scope, and inversed regioselectivity make it a complementary method to the previously developed iron catalytic system.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Wang C
Dalian Institute of Chemical Physics, Chinese Academy of Sciences, 457 Zhongshan Road, Dalian 116023, China.
Wang D
No affiliation info available
Xu F
No affiliation info available
Pan B
No affiliation info available
Wan B
No affiliation info available

MeSH

AlkynesAminopyridinesCatalysisCyanamideCyclizationIronMolecular StructureTemperature

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

23373593

Citation

Wang, Chunxiang, et al. "Iron-catalyzed Cycloaddition Reaction of Diynes and Cyanamides at Room Temperature." The Journal of Organic Chemistry, vol. 78, no. 7, 2013, pp. 3065-72.
Wang C, Wang D, Xu F, et al. Iron-catalyzed cycloaddition reaction of diynes and cyanamides at room temperature. J Org Chem. 2013;78(7):3065-72.
Wang, C., Wang, D., Xu, F., Pan, B., & Wan, B. (2013). Iron-catalyzed cycloaddition reaction of diynes and cyanamides at room temperature. The Journal of Organic Chemistry, 78(7), 3065-72. https://doi.org/10.1021/jo400057t
Wang C, et al. Iron-catalyzed Cycloaddition Reaction of Diynes and Cyanamides at Room Temperature. J Org Chem. 2013 Apr 5;78(7):3065-72. PubMed PMID: 23373593.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Iron-catalyzed cycloaddition reaction of diynes and cyanamides at room temperature. AU - Wang,Chunxiang, AU - Wang,Dongping, AU - Xu,Fen, AU - Pan,Bin, AU - Wan,Boshun, Y1 - 2013/02/12/ PY - 2013/2/5/entrez PY - 2013/2/5/pubmed PY - 2013/10/1/medline SP - 3065 EP - 72 JF - The Journal of organic chemistry JO - J Org Chem VL - 78 IS - 7 N2 - An iron-catalyzed [2 + 2 + 2] cycloaddition reaction of diynes and cyanamides at room temperature is reported. Highly substituted 2-aminopyridines were obtained in good to excellent yields with high regioselectivity. Insights toward the reaction process were investigated through in situ IR spectra and control experiments. In this iron-catalyzed cycloaddition reaction, the active iron species was generated only in the presence of both alkynes and nitriles. The lower reaction temperature, broad substrates scope, and inversed regioselectivity make it a complementary method to the previously developed iron catalytic system. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/23373593/Iron_catalyzed_cycloaddition_reaction_of_diynes_and_cyanamides_at_room_temperature_ L2 - https://doi.org/10.1021/jo400057t DB - PRIME DP - Unbound Medicine ER -