Synthesis of novel tetra- and pentacyclic benzosultam scaffolds via domino Knoevenagel hetero-Diels–Alder reactions in water

被引:0
|
作者
Mehdi Ghandi
Shahab Sheibani
Masoud Sadeghzadeh
Fariba Johari Daha
Maciej Kubicki
机构
[1] University of Tehran,School of Chemistry, College of Science
[2] Radioisotope Research Group,Faculty of Chemistry
[3] NSTRI,undefined
[4] Adam Mickiewicz University in Poznan,undefined
关键词
Domino Knoevenagel hetero-Diels–Alder; Dihydropyrano[3,2-; ]chromen-5-ones; Dihydropyranopyrimidines; Benzosultams;
D O I
暂无
中图分类号
学科分类号
摘要
An efficient catalyst-free and diastereoselective synthesis of novel dihydropyrano[2,3-d]pyrimidine and dihydropyrano[3,2-c]chromen-annulated benzosultams is described. A number of (E)-N-(2-formylphenyl)-N-methyl-2-phenylethenesulfonamides were synthesized and underwent a one-pot domino Knoevenagel hetero-Diels–Alder reaction, respectively, with N,N-dimethylbarbituric acid and 4-hydroxycoumarin in water, giving the desired products, in moderate to excellent yields.
引用
收藏
页码:1057 / 1065
页数:8
相关论文
共 50 条
  • [41] One-Pot Synthesis of Dihydropyrans via CO2 Reduction and Domino Knoevenagel/oxa-Diels-Alder Reactions
    Takaishi, Kazuto
    Nishimura, Ritsuki
    Toda, Yuha
    Morishita, Hajime
    Ema, Tadashi
    ORGANIC LETTERS, 2023, : 1370 - 1374
  • [42] Synthesis of Pyrano[3,4-c]chromene Skeleton via CuI-Mediated Domino Knoevenagel Hetero-Diels-Alder Reaction
    Mollazadeh, Marjan
    Khoshkholgh, Malihe Javan
    Balalaie, Saeed
    Rominger, Frank
    Bijanzadeh, Hamid Reza
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2010, 47 (05) : 1200 - 1208
  • [43] Synthesis of Tetrahydropyrazolo[4′,3′:5,6]pyrano[3,4-c]quinolones by Domino Knoevenagel/Hetero Diels-Alder Reactions
    Kiamehr, Mostafa
    Mohammadkhani, Leyla
    Khodabakhshi, Mohammad Reza
    Jafari, Behzad
    Langer, Peter
    SYNLETT, 2019, 30 (15) : 1782 - 1786
  • [44] Three-component tandem Knoevenagel/hetero Diels-Alder reactions total synthesis of (±)-preethulia coumarin
    Appendino, G
    Cravotto, G
    Minassi, A
    Palmisano, G
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2001, 2001 (19) : 3711 - 3717
  • [45] CuI-IONIC LIQUIDS AS EFFICIENT REACTION MEDIA FOR THE SYNTHESIS OF PYRAN SKELETON VIA DOMINO KNOEVENAGEL-HETERO-DIELS-ALDER REACTION WITH UNACTIVATED ALKYNES
    Balalaie, Saeed
    Azizian, Javad
    Shameli, Abolghasem
    Bijanzadeh, Hamid Reza
    SYNTHETIC COMMUNICATIONS, 2013, 43 (13) : 1787 - 1795
  • [46] Ethylenediamine diacetate (EDDA)-catalyzed one-pot synthesis of tetrahydroquinolines by domino knoevenagel/hetero Diels-Alder reactions from 1,3-dicarbonyls
    Lee, Yong Rok
    Hung, Thai Viet
    TETRAHEDRON, 2008, 64 (30-31) : 7338 - 7346
  • [47] High chemoselectivity in microwave accelerated intramolecular domino Knoevenagel hetero Diels-Alder reactions - an efficient synthesis of pyrano[3-2c]coumarin frameworks
    Shanmugasundaram, M
    Manikandan, S
    Raghunathan, R
    TETRAHEDRON, 2002, 58 (05) : 997 - 1003
  • [48] First example of ionic liquids-promoted domino knoevenagel hetero-Diels-Alder reactions:: A facile synthesis of pyrano[3,2-c]coumarins
    Yadav, JS
    Reddy, BVS
    Naveenkumar, V
    Rao, RS
    Nagaiah, K
    SYNTHESIS-STUTTGART, 2004, (11): : 1783 - 1788
  • [49] Mechanisms of the Knoevenagel hetero Diels-Alder sequence in multicomponent reactions to dihydropyrans: experimental and theoretical investigations into the role of water
    Frapper, Gilles
    Bachmann, Christian
    Gu, Yanlong
    De Sousa, Rodolphe Coval
    Jerome, Francois
    PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2011, 13 (02) : 628 - 636
  • [50] A new domino Knoevenagel-hetero-Diels-Alder reaction: an efficient catalyst-free synthesis of novel thiochromone-annulated thiopyranocoumarin derivatives in aqueous medium
    Moghaddam, Firouz Matloubi
    Kiamehr, Mostafa
    Khodabakhshi, Mohammad Reza
    Mirjafary, Zohreh
    Fathi, Shaghayegh
    Saeidian, Hamdollah
    TETRAHEDRON, 2010, 66 (45) : 8615 - 8622