Diels-Alder reactions of five-membered heterocycles containing one heteroatom

被引：30
|
作者：
Ding, Xiaoyuan [1 ]
Nguyen, Son T. [1 ]
Williams, John D. [1 ]
Peet, Norton P. [1 ]
机构：
[1] Microbiotix Inc, Dept Chem, Worcester, MA 01605 USA
来源：
TETRAHEDRON LETTERS | 2014年 / 55卷 / 51期
关键词：
Diels-Alder reactions; Dienes; Dienophiles; Acid-catalyzed reactions; SERIES; ROUTE;
D O I：
10.1016/j.tetlet.2014.10.114
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Diels-Alder reactions of five-membered heterocycles containing one heteroatom with an N-arylmaleimide were studied. Cycloaddition of 2,5-dimethylfuran (4) with 2-(4-methylphenyl)maleimide (3) in toluene at 60 degrees C gave bicyclic adduct 5. Cycloadditions of 3 with 2,5-dimethylthiophene (11) and 1,2,5-trimethylpyrrole (14) were also studied. Interestingly, the bicyclic compound 5 cleanly rearranged, with loss of water, when treated with p-toluenesulfonic acid in toluene at 80 degrees C to give 4,7-dimethyl-2-p-tolylisoindoline-1, 3-dione (6). (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码：7002 / 7006
页数：5
相关论文
共 50 条
  • [1] Diels-Alder reactions between cyclic five-membered dienes and acetylene
    Vijaya, R
    Dinadayalane, TC
    Sastry, GN
    JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM, 2002, 589 : 291 - 299
  • [2] Five-Membered Aromatic Heterocycles in Diels-Alder Cycloaddition Reactions: Theoretical Studies as a Complement of the Experimental Researches
    Brasca, Romina
    Della Rosa, Claudia
    Kneeteman, Maria
    Mancini, Pedro M. E.
    LETTERS IN ORGANIC CHEMISTRY, 2011, 8 (02) : 82 - 87
  • [3] Tautomerism of heterocycles: Five-membered rings with one heteroatom
    Friedrichsen, W
    Traulsen, T
    Elguero, J
    Katritzky, AR
    ADVANCES IN HETEROCYCLIC CHEMISTRY, VOL 76, 2000, 76 : 85 - 156
  • [4] Why Do Five-Membered Heterocyclic Compounds Sometimes Not Participate in Polar Diels-Alder Reactions?
    Domingo, Luis R.
    Perez, Patricia
    Ortega, Daniela E.
    JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (06): : 2462 - 2471
  • [5] Synthesis of Five-Membered Heterocycles Containing Nitrogen Heteroatom Under Ultrasonic Irradiation
    Kaur, Navjeet
    MINI-REVIEWS IN ORGANIC CHEMISTRY, 2019, 16 (05) : 481 - 503
  • [6] Reactivities of five-membered heterocycles in hydride transfer reactions
    Lee, ISH
    Jeoung, EH
    JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (21): : 7275 - 7279
  • [7] 5-MEMBERED AROMATIC HETEROCYCLES AS DIENOPHILES IN DIELS-ALDER REACTIONS - FURAN, PYRROLE, AND INDOLE
    WENKERT, E
    MOELLER, PDR
    PIETTRE, SR
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (21) : 7188 - 7194
  • [8] Density functional theory study of the Diels-Alder reactivities of [b]-annelated cyclic five-membered dienes
    Punnagai, M
    Dinadayalane, TC
    Sastry, GN
    JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 2004, 17 (02) : 152 - 161
  • [9] Five-membered heterocycles. Part IV:: Impact of heteroatom on benzazole aromaticity
    Karolak-Wojciechowska, J.
    Mrozek, A.
    Czylkowski, R.
    Tekiner-Gulbas, B.
    Aki-Sener, E.
    Yalcin, I.
    JOURNAL OF MOLECULAR STRUCTURE, 2007, 839 (1-3) : 125 - 131
  • [10] Synthetic Routes to Coumarin(Benzopyrone)-Fused Five-Membered Aromatic Heterocycles Built on the α-Pyrone Moiety. Part 1: Five-Membered Aromatic Rings with One Heteroatom
    El-Sawy, Eslam Reda
    Abdelwahab, Ahmed Bakr
    Kirsch, Gilbert
    MOLECULES, 2021, 26 (02):
12345