Facile Gold-Catalyzed Heterocyclization of Terminal Alkynes and Cyanamides Leading to Substituted 2-Amino-1,3-Oxazoles

被引：69
|
作者：
Rassadin, Valentin A. [1 ]
Boyarskiy, Vadim P. [1 ]
Kukushkin, Vadim Yu [1 ]
机构：
[1] St Petersburg State Univ, Inst Chem, St Petersburg 198504, Russia
来源：
ORGANIC LETTERS | 2015年 / 17卷 / 14期
关键词：
EFFICIENT SYNTHESIS; OXIDATIVE CYCLIZATION; REARRANGEMENT; COMPLEXES; CARBENES; INHIBITOR; DISCOVERY; LIGANDS; CYCLOISOMERIZATION; TRANSFORMATIONS;
D O I：
10.1021/acs.orglett.5b01592
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Facile gold-catalyzed heterocyclization based upon intermolecular trapping of the generated alpha-oxo gold carbenes with various cyanamides (RRNCN)-R-2-N-3 (R-2/R-3 = Alk/Alk, -(CH2)(2)O(CH2)(2)-, Ar/Ar, Ar/H) has been developed. In most cases, 2-amino-1,3-oxazoles fiinctionalized at the nitrogen atom as well as at the fifth position of the heterocyclic ring (12 examples) were isolated hi good to moderate yields.
引用
收藏
页码：3502 / 3505
页数：4
相关论文
共 37 条
  • [21] Enantioselective Synthesis of α-Substituted Serine Derivatives via Cu-Catalyzed Oxidative Desymmetrization of 2-Amino-1,3-diols
    Yamamoto, Kosuke
    Ishimaru, Shota
    Oyama, Tatsuya
    Tanigawa, Satoko
    Kuriyama, Masami
    Onomura, Osamu
    ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2019, 23 (04) : 660 - 666
  • [22] Enantioselective Synthesis of 2-Substituted 2-Hydroxymethylaziridines by Copper-Catalyzed Sulfonylative Desymmetrization of 2-Amino-1,3-Diols
    Yamamoto, Kosuke
    Sakata, Eibu
    Uehara, Anri
    Kuriyama, Masami
    Onomura, Osamu
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2025, 14 (03)
  • [23] Gold-Catalyzed Oxidation Terminal Alkyne: An Approach to Synthesize Substituted Dihydronaphthalen-2(1H)-ones and Phenanthrenols
    Ling, Hui-Bo
    Chen, Zi-Sheng
    Yang, Fang
    Xu, Bin
    Gao, Jin-Ming
    Ji, Kegong
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (13): : 7070 - 7076
  • [24] Gold-Catalyzed Cadiot-Chodkiewicz-type Cross-Coupling of Terminal Alkynes with Alkynyl Hypervalent Iodine Reagents: Highly Selective Synthesis of Unsymmetrical 1,3-Diynes
    Li, Xiangdong
    Xie, Xin
    Sun, Ning
    Liu, Yuanhong
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (24) : 6994 - 6998
  • [25] Tetrasubstituted 1,3-Enynes by Gold-Catalyzed Direct C(sp2)-H Alkynylation of Acceptor-Substituted Enamines
    Han, Chunyu
    Tian, Xianhai
    Zhang, Huili
    Rominger, Frank
    Hashmi, A. Stephen K.
    ORGANIC LETTERS, 2021, 23 (12) : 4764 - 4768
  • [26] Intermolecular Reaction of Internal Alkynes and Imines: Propargyl Tosylates as Key Partners in a Gold-Catalyzed [4+1] Unusual Cyclization Leading to Cyclopent-2-enimines
    Suarez-Pantiga, Samuel
    Rubio, Eduardo
    Alvarez-Rua, Carmen
    Gonzalez, Jose M.
    ORGANIC LETTERS, 2009, 11 (01) : 13 - 16
  • [27] Gold(III)-Catalyzed 1,4-Nucleophilic Addition: Facile Approach to Prepare 2-Amino-1,4-naphthalenedione and 6-Amino-5,8-quinolinedione Derivatives
    Jiang, Chunhui
    Wang, Shaozhong
    SYNLETT, 2009, (07) : 1099 - 1102
  • [28] Gold-Catalyzed Divergent N/O-Vinylations of trans-2-Butene-1,4-amino Alcohols with Alkynes and the Cascade Rearrangements/Cyclizations to Dihydropyrroles and Dihydrofurans
    Zhang, Xiao-Qian
    Zhang, Congdi
    Hu, Zhiyou
    Wang, Youliang
    ORGANIC LETTERS, 2023, 25 (31) : 5800 - 5805
  • [29] Gold-catalyzed oxidation of terminal alkynes to glyoxals and their reactions with 2-phenylimidazo [1,2-a]pyridines: one-pot synthesis of 1,2-diones
    Liao, Shengrong
    Xu, Huayan
    Yang, Bin
    Wang, Junfeng
    Zhou, Xuefeng
    Lin, Xiuping
    Liu, Yonghong
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (40) : 8735 - 8739
  • [30] External oxidant-free, ligand-assisted heterogeneous gold-catalyzed C(sp2)-C(sp) cross-coupling of aryldiazonium salts with terminal alkynes
    Song, Boling
    Li, Jiajia
    Hao, Wenyan
    Cai, Mingzhong
    CATALYSIS SCIENCE & TECHNOLOGY, 2024, 14 (15) : 4354 - 4365
1234