[3+2] Cycloaddition reactions of 1-substituted 3,3,3-trifluoropropenes with isonitriles – synthesis of pyrroles and pyrrolines

被引：0
|
作者：
Yuriy N. Markitanov
Vadim M. Timoshenko
Eduard B. Rusanov
Yuriy G. Shermolovich
机构：
[1] Institute of Organic Chemistry,
[2] National Academy of Sciences of Ukraine,undefined
来源：
Chemistry of Heterocyclic Compounds | 2021年 / 57卷
关键词：
ethyl isocyanoacetate; pyrrole; pyrrolidine; pyrroline; sulfamide; sulfone; sulfoximine; tosylmethyl isocyanide; trifluoromethyl group; cycloaddition;
D O I：
暂无
中图分类号：
学科分类号：
摘要：
Cycloaddition reactions of 3,3,3-trifluoropropene derivatives containing an alkoxycarbonyl, sulfonyl, sulfoximine, or sulfamide substituent in position 1 with ethyl isocyanoacetate proceed with the formation of 3-(trifluoromethyl)-2,3-dihydro-1H-pyrroles, whereas their reactions with tosylmethyl isocyanide lead to the formation of 4-(trifluoromethyl)-1H-pyrroles.
引用
收藏
页码：253 / 260
页数：7
相关论文
共 50 条
  • [41] Regioselective Synthesis of 5-Trifluoromethylpyrazoles by [3+2] Cycloaddition of Nitrile Imines and 2-Bromo-3,3,3-trifluoropropene
    Zeng, Hao
    Fang, Xiaojie
    Yang, Zhiyi
    Zhu, Chuanle
    Jiang, Huanfeng
    JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (03): : 2810 - 2819
  • [42] REGIOSELECTIVITY OF [3+2]CYCLOADDITION REACTIONS OF MESOIONIC 1,3-DITHIOLONES TO UNSYMMETRICALLY SUBSTITUTED ALKYNES
    GOTTHARDT, H
    WEISSHUHN, CM
    CHEMISCHE BERICHTE-RECUEIL, 1978, 111 (05): : 2028 - 2036
  • [43] Synthesis of indanes via a [3+2] cycloaddition
    Lantaño, B
    Finkielsztein, LM
    Alesso, EN
    Aguirre, JM
    Moltrasio, GY
    MOLECULES, 2000, 5 (03) : 416 - 417
  • [44] APPLICATION OF [3+2]-CYCLOADDITION IN THE SYNTHESIS OF VALDECOXIB
    Reddy, Anumula Raghupathi
    Goverdhan, Gilla
    Sampath, Aalla
    Mukkanti, Khagga
    Reddy, Padi Pratap
    Bandichhor, Rakeshwar
    SYNTHETIC COMMUNICATIONS, 2012, 42 (05) : 639 - 649
  • [45] Synthesis of fluorinated 3-pyrrolines and pyrroles via [3+2] annulation of N-aryl fluorinated imines with allenoates catalyzed by phosphine
    Zhu, Zhentong
    Guo, Yuwei
    Wang, Xiaojun
    Wu, Fanhong
    Wu, Yongming
    JOURNAL OF FLUORINE CHEMISTRY, 2017, 195 : 102 - 107
  • [46] Synthesis of trifluoromethylated pyrazolidines by [3+2] cycloaddition
    Peng, Xiansha
    Huang, Danfeng
    Wang, Ke-Hu
    Wang, Yalin
    Wang, Juanjuan
    Su, Yingpeng
    Hu, Yulai
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (29) : 6214 - 6222
  • [47] Synthesis of New Thienopyridine Derivatives by [3+2]- and [2+2]-Cycloaddition Reactions
    Milen, Matyas
    Abranyi-Balogh, Peter
    Dancso, Andras
    Keglevich, Gyoergy
    SYNTHESIS-STUTTGART, 2012, 44 (22): : 3447 - 3452
  • [48] Base-mediated ynone-isocyanide [3+2] cycloaddition: a general method to 2,3,4-tri-substituted 1-H-pyrroles and bis-pyrroles
    Kumar, Ankit
    Mishra, Pawan K.
    Verma, Akhilesh K.
    CHEMICAL COMMUNICATIONS, 2023, 59 (47) : 7263 - 7266
  • [49] [3+2] cycloaddition reactions of cyclopropyl imines with enones
    Liu, Lei
    Montgomery, John
    ORGANIC LETTERS, 2007, 9 (20) : 3885 - 3887
  • [50] Understanding the mechanism and regio- and stereo selectivity of [3+2] cycloaddition reactions between substituted azomethine ylide and 3,3,3-trifluoro-1-nitroprop-1-ene, within the molecular electron density theory
    Sobhi, Chafia
    Merzoud, Lynda
    Bouasla, Souad
    Nacereddine, Abdelmalek Khorief
    Morell, Christophe
    Chermette, Henry
    JOURNAL OF COMPUTATIONAL CHEMISTRY, 2023, 44 (12) : 1208 - 1220
12345