DIELS-ALDER REACTION OF 2-(CYCLIC AMINO)-SUBSTITUTED 3-FURANCARBONITRILES WITH MALEIMIDES TO PHTHALIMIDES

被引:4
|
作者
Maruoka, Hiroshi [1 ]
Okabe, Fumi [1 ]
Koutake, Yoshimichi [1 ]
Fujioka, Toshihiro [1 ]
Yamagata, Kenji [1 ]
机构
[1] Fukuoka Univ, Fac Pharmaceut Sci, Jonan Ku, Fukuoka 8140180, Japan
关键词
Diels-Alder Reaction; Cycloaddition; Furan; Phthalimide; Maleimide; FACTOR-ALPHA PRODUCTION; VERSUS-HOST-DISEASE; MICROWAVE IRRADIATION; ANTIINFLAMMATORY ACTIVITY; THALIDOMIDE; FURANS; ANILINES; ANALOGS; DERIVATIVES; ANHYDRIDES;
D O I
10.3987/COM-08-S(F)34
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient Diels-Alder reaction is described in the furan series, leading to phthalimides in high yields. Thermal treatment of 2-(4-morpholinyl, 1-piperidinyl, and 1-pyrrolidinyl)-3-furancarbortitfiles with maleimide derivatives, e.g. maleimide, N-methylmaleimide, N-benzylmaleimide, N-phenylmaleimide and N-(4-nitrophenyl)maleimide, in boiling acetic acid caused a [4 + 2] cycloaddition reaction to give the corresponding phthalimide derivatives.
引用
收藏
页码:617 / 628
页数:12
相关论文
共 50 条
  • [1] SYNTHESIS OF PHENYLATED PHTHALIMIDES - DIELS-ALDER REACTION OF TETRAPHENYLCYCLOPENTADIENONE WITH MALEIMIDES
    HARRIS, FW
    NORRIS, SO
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1972, 9 (06) : 1251 - 1253
  • [2] DIELS-ALDER REACTION OF TETRACYCLONE WITH SOME MALEIMIDES
    KHALIFA, MAE
    ABDOU, SEI
    ZAYED, EM
    CURRENT SCIENCE, 1975, 44 (22): : 797 - 800
  • [3] DIELS-ALDER REACTIONS WITH SOME N-SUBSTITUTED MALEIMIDES
    KHATTAB, SA
    KHALIFA, MA
    MAHGOUB, SA
    JOURNAL FUR PRAKTISCHE CHEMIE, 1977, 319 (03): : 432 - 438
  • [4] Synthesis of Diels-Alder adducts of hexachlorocyclopentadiene and substituted maleimides.
    Colpo, JL
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2000, 219 : U347 - U347
  • [5] THE DIELS-ALDER REACTION OF SUBSTITUTED FURANS
    HOLSWORTH, D
    AGER, DJ
    OHIO JOURNAL OF SCIENCE, 1986, 86 (02) : 25 - 25
  • [6] Diels-Alder reaction of 2-amino-substituted furans as a method for preparing substituted anilines
    Padwa, A
    Dimitroff, M
    Waterson, AG
    Wu, TH
    JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (12): : 4088 - 4096
  • [7] A deep cavitand catalyzes the Diels-Alder reaction of bound maleimides
    Hooley, Richard J.
    Rebek, Julius, Jr.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2007, 5 (22) : 3631 - 3636
  • [8] Cycloaddition of nitrile imines and Diels-Alder reaction of anthracene to isoxazolyl maleimides
    Rajanarendar, E
    Srinivas, M
    Karunakar, D
    Ramu, K
    HETEROCYCLIC COMMUNICATIONS, 2005, 11 (05) : 441 - 444
  • [9] DIELS-ALDER REACTION CURING OF CHLOROBUTYL RUBBER BY BIS-MALEIMIDES
    HO, K
    STEEVENSZ, R
    RUBBER CHEMISTRY AND TECHNOLOGY, 1989, 62 (01): : 42 - 54
  • [10] Ionic Liquid promoted Diels-Alder Reaction between anthrone and maleimides
    Mirgane, Nitin A.
    Kotwal, Sandip B.
    Karnik, Anil V.
    CENTRAL EUROPEAN JOURNAL OF CHEMISTRY, 2010, 8 (02): : 356 - 360