Use of Dialkyl Acetylenedicarboxylates in the Multicomponent Synthesis of Heterocyclic Structures

被引:3
|
作者
Rezvanian, Atieh [1 ]
Khodadadi, Behnoosh [1 ]
Tafreshi, Sepideh [1 ]
机构
[1] Alzahra Univ, Fac Chem, Dept Organ Chem, Tehran, Iran
来源
CHEMISTRYSELECT | 2022年 / 7卷 / 34期
关键词
Multicomponent reactions; dialkyl acetylenedicarboxylate; seven-membered rings; Six-membered rings; five-membered rings; ONE-POT SYNTHESIS; ACTIVATED DOUBLE-BONDS; ACIDIC-IONIC-LIQUID; EFFICIENT SYNTHESIS; DIMETHYL ACETYLENEDICARBOXYLATE; DIASTEREOSELECTIVE SYNTHESIS; REGIOSELECTIVE SYNTHESIS; THIOPHENE DERIVATIVES; BIOLOGICAL EVALUATION; 3-COMPONENT SYNTHESIS;
D O I
10.1002/slct.202202360
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Dialkyl acetylenedicarboxylates (DAAD) are the class of acetylenic compounds that are broadly used in organic synthesis in a noticeable quantity. Their wide application has made them an important moiety in heterocyclic compounds and drug discovery programs. Dialkyl acetylenedicarboxylate is a di-ester in which the ester groups are conjugated with a carbon-carbon triple bond. As such, the molecule is very electrophilic, and is broadly used as a dienophile in various cycloaddition reactions, for example the Diels-Alder reaction. In addition, it is a strong Michael acceptor. Due the importance of dialkyl acetylenedicarboxylate in organic synthesis, we are trying to show the applications of this compound in the synthesis of different heterocycles using multicomponent reactions. In this review, we show recent advances (2016-2022) for the synthesis of various heterocycles that have different ring sizes (five, six and seven membered, Spiro and fused heterocycles), using DAAD via multicomponent reactions.
引用
收藏
页数:50
相关论文
共 50 条
  • [21] SYNTHESIS, PROPERTIES AND REACTIVITY OF METAL HETEROCYCLIC-COMPOUNDS .83. SYNTHESIS OF DIFFERENTLY SUBSTITUTED FURANS BY COBALT-INDUCED CYCLOCOTRIMERIZATION OF A P=S FUNCTION WITH DIALKYL ACETYLENEDICARBOXYLATES
    LINDNER, E
    SCHLENKER, T
    FAWZI, R
    MAICHLE, C
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1993, 459 (1-2) : 303 - 310
  • [22] Copper-Catalyzed Annulation of α,β-Unsaturated Ketoximes with Dialkyl Acetylenedicarboxylates for the Synthesis of Highly Substituted Pyridines
    He, Shi-Mei
    Yang, Yun-Bo
    Liu, Lv-Yan
    Yu, Ning
    Zhou, Yu-Qiang
    Zhou, Jia-Hao
    Zheng, Mei-Jun
    Jin, Xiao-Kun
    Jiang, Kun
    Wei, Ye
    ORGANIC LETTERS, 2025, 27 (05) : 1100 - 1105
  • [23] Ionic Liquid-Mediated, Rapid N-Alkylation of Heterocyclic Compounds with Trialkyl Phosphites in the Presence of Dialkyl Acetylenedicarboxylates
    Hassanabadi, Alireza
    Mosslemin, Mohammad H.
    Anary-Abbasinejad, Mohammad
    Kalantarinejad, Azadeh
    Shirazi, Mozhdeh Jerjisi
    E-JOURNAL OF CHEMISTRY, 2012, 9 (04) : 2074 - 2078
  • [24] An Efficient Synthesis of Dialkyl 2-(Diphenoxyphosphoryl)-3-(alkylthio)succinates from Alkylthiols, Triphenyl Phosphite and Dialkyl Acetylenedicarboxylates
    Yavari, I.
    Hajinasiri, R.
    Sayyed-Alangi, S. Z.
    Iravani, N.
    JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2009, 6 (04) : 705 - 709
  • [25] SYNTHESIS OF WITH ACETYLENEDICARBOXYLATES
    BAUMGARTH, M
    CHEMIKER-ZEITUNG, 1972, 96 (07): : 361 - +
  • [26] Multicomponent and domino reactions in the synthesis of heterocyclic compounds
    Voskressensky, L. G.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2012, 48 (04) : 535 - 535
  • [27] Multicomponent interphase synthesis of heterocyclic compounds (Review)
    Ivantsova, M. N.
    Tokareva, M. I.
    Mironov, M. A.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2012, 48 (04) : 584 - 600
  • [28] Multicomponent interphase synthesis of heterocyclic compounds (Review)
    M. N. Ivantsova
    M. I. Tokareva
    M. A. Mironov
    Chemistry of Heterocyclic Compounds, 2012, 48 : 584 - 600
  • [29] Multicomponent and domino reactions in the synthesis of heterocyclic compounds
    L. G. Voskressensky
    Chemistry of Heterocyclic Compounds, 2012, 48 : 535 - 535
  • [30] HClO4-SiO2 catalyzed multicomponent reactions for the synthesis of privileged heterocyclic structures
    Mandal, Pintu Kumar
    Misra, Anup Kumar
    LETTERS IN ORGANIC CHEMISTRY, 2006, 3 (11) : 848 - 853