Triphenylarsine as an Efficient Catalyst in Diastereospecific Synthesis of N-Vinyl Heterocyclic Compounds

被引:9
|
作者
Maghsoodlou, Malek Taher [1 ]
Heydari, Reza [1 ]
Habibi-Khorassani, Sayyed Mostafa [1 ]
Hazeri, Nourollah [1 ]
Lashkari, Mojtaba [1 ]
Rostamizadeh, Mohsen [1 ]
Sajadikhah, Seyed Sajad [1 ]
机构
[1] Univ Sistan & Baluchestan, Dept Chem, Zahedan, Iran
关键词
Dialkyl acetylenedicarboxylate; N-H heterocyclic compounds; N-vinylation; triphenylarsine; STABLE PHOSPHORUS YLIDES; DIELS-ALDER REACTION; ONE-POT SYNTHESIS; ACETYLENIC ESTERS; ANTIPARASITIC NITROIMIDAZOLES; AMINE-DERIVATIVES; NITROGEN; TRIPHENYLPHOSPHINE; ENAMIDES; 1-VINYLIMIDAZOLE;
D O I
10.1080/00397911003629432
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[image omitted] A diastereospecific synthesis of N-vinyl heterocyclic compounds is described from a reaction of dialkyl acetylenedicarboxylate and N-H heterocyclic compounds, such as phthalimide, saccharin, 3(2H)-pyridazinone, isatin, maleimide, 2,4-thiazolidinedione, 2-benzoxazolinione and 6-chloro-2-benzoxazolinione, in the presence of triphenylarsine as an efficient catalyst, in excellent yield. The presented one-pot method is simple and effective with mild conditions.
引用
收藏
页码:569 / 578
页数:10
相关论文
共 50 条
  • [1] SYNTHESIS OF N-VINYL SULFONAMIDES
    CAIRNS, TL
    SAUER, JC
    JOURNAL OF ORGANIC CHEMISTRY, 1955, 20 (05): : 627 - 629
  • [2] Synthesis of N-vinyl caprolactam
    Feng Shubo
    Li Shuyuan
    He Cunfeng
    Zheng Erli
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 234
  • [3] Synthesis of N-vinyl caprolactam
    Feng Shubo
    Li Shuyuan
    He Cunfeng
    Zheng Erli
    Tang Xinliang
    CATALYSIS TODAY, 2009, 140 (3-4) : 169 - 173
  • [4] ADDITION OF HYDROPEROXIDES TO N-VINYL COMPOUNDS
    LEDERER, M
    CHEMISCHE BERICHTE-RECUEIL, 1972, 105 (07): : 2169 - &
  • [5] Regioselective Synthesis of N-Vinyl Pyrazoles from Vinyl Sulfonium Salts with Diazo Compounds
    Wang, Shichong
    Xu, Huayan
    Zhang, Ruoyu
    Zhang, Siyu
    Chai, Yun
    Yang, Bingchuan
    Zhao, Jingjing
    Xu, Yuanqing
    Li, Pan
    ORGANIC LETTERS, 2023, 25 (36) : 6746 - 6750
  • [6] COMPLEX COMPOUNDS SYNTHESIS WITH CHARGE MIGRATION BASED ON N-VINYL PHENOTHIAZINE
    SKVORTSOVA, GG
    SHOSTAKO.MF
    KUROV, GN
    ZHURNAL ORGANICHESKOI KHIMII, 1972, 8 (02): : 382 - +
  • [7] Copper-mediated synthesis of N-vinyl ynamides from N-vinyl carbamates
    Le Fouler, Vincent
    Duret, Guillaume
    Bisseret, Philippe
    Blanchard, Nicolas
    TETRAHEDRON LETTERS, 2018, 59 (36) : 3349 - 3352
  • [8] Modular Synthesis of N-Vinyl Benzotriazoles
    Singh, Govindra
    Kumar, Rakesh
    Swett, Jorge
    Zajc, Barbara
    ORGANIC LETTERS, 2013, 15 (16) : 4086 - 4089
  • [9] A general synthesis of N-vinyl nitrones
    Denmark, Scott E.
    Montgomery, Justin I.
    JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (16): : 6211 - 6220
  • [10] REACTION OF VINYL ETHERS WITH ACIDIC IMINO COMPOUNDS - A NEW SYNTHESIS OF SOME N-VINYL IMIDES
    FURUKAWA, J
    ONISHI, A
    TSURUTA, T
    JOURNAL OF ORGANIC CHEMISTRY, 1958, 23 (05): : 672 - 676