Revisited synthesis of fused diazepines from 3-(3-aryl-3-oxopropenyl)chromen-4-ones and binucleophilic amino enones in a three-step domino process

被引：4
作者：
Alizadeh, Abdolali [1 ]
Bagherinejad, Akram [1 ]
机构：
[1] Tarbiat Modares Univ, Dept Chem, POB 14115-175, Tehran, Iran
来源：
MENDELEEV COMMUNICATIONS | 2023年 / 33卷 / 03期
关键词：
3-vinylchromones; binucleophilic amino enones; catalyst-free reactions; three-step domino reaction; tetracyclic compounds; pyrido-fused compounds; dibenzo[b; f]pyrido-[1; 2-d][1; 4]diazepines; DERIVATIVES; NMR;
D O I：
10.1016/j.mencom.2023.04.032
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The synthesis of tetracyclic 11,12,13,14b-tetrahydrodi-benzo[b,f]pyrido[1,2-d][1,4]diazepines was revisited via a catalyst-free three-step domino reaction involving a pyrone ring-opening/aza-Michael addition/intramolecular cyclization, the reactants having been o-arylenediamine-dimedone adducts and 3-(3-aryl-3-oxopropenyl)chromen-4-ones. The 3-positioned exocyclic a,b-enone fragment on the chromone moiety is involved in the cyclization into the final products at the last step of the process.
引用
收藏
页码：401 / 403
页数：3
相关论文
共 12 条
  • [1] An Efficient Three-Component Synthesis of Benzimidazo[1,2-a]-quinoline-6-carbonitriles
    Adib, Mehdi
    Zainali, Mohsen
    Kim, Il
    [J]. SYNLETT, 2016, 27 (12) : 1844 - 1847
  • [2] Synthesis of tetracyclic pyrido-fused dibenzodiazepines via a catalyst-free cascade reaction
    Alizadeh, Abdolali
    Bagherinejad, Akram
    [J]. MOLECULAR DIVERSITY, 2021, 25 (04) : 2237 - 2246
  • [3] Efficient one pot and chemoselective synthesis of functionalized 3-bromo-4,5-dihydroisoxazole derivatives &ITvia &IT1,3-dipolar cycloaddition reactions of nitrile oxides
    Alizadeh, Abdolali
    Roosta, Atefeh
    Rezaiyehrad, Reza
    Halvagar, Mohammadreza
    [J]. TETRAHEDRON, 2017, 73 (48) : 6706 - 6711
  • [4] Dibenzo[b,e][1,4]diazepin-1-ones and their Ring-Opened Derivatives: Revisited Synthesis, 2D NMR and Crystal Structure
    Cherfaoui, Brahim
    Lakhdari, Houria
    Bennamane, Norah
    Ameraoui, Rachid
    Talhi, Oualid
    Paz, Filipe A. Almeida
    Bachari, Khaldoun
    Kirsch, Gilbert
    Nejar-Bellara, Kolli
    Silva, Artur M. S.
    [J]. SYNLETT, 2017, 28 (17) : 2247 - 2252
  • [5] Electron-deficient dienes. 5. An inverse-electron-demand Diels-Alder approach to 2-substituted 4-methoxyxanthones and 3,4-dimethoxyxanthones
    Dang, Anh-Thu
    Miller, David O.
    Dawe, Louise N.
    Bodwell, Graham J.
    [J]. ORGANIC LETTERS, 2008, 10 (02) : 233 - 236
  • [6] Organocatalytic [10+4] cycloadditions for the synthesis of functionalised benzo[a]azulenes
    Giardinetti, Maxime
    Jessen, Nicolaj Inunnguaq
    Christensen, Mette Louise
    Jorgensen, Karl Anker
    [J]. CHEMICAL COMMUNICATIONS, 2019, 55 (02) : 202 - 205
  • [7] Direct construction of xanthene and benzophenone derivatives via Bronsted acid controlled Diels-Alder reaction of 3-vinylchromones and arynes
    Huang, Xu-Jiao
    Tao, Yuan
    Li, Yue-Kun
    Wu, Xin-Yan
    Sha, Feng
    [J]. TETRAHEDRON, 2016, 72 (52) : 8565 - 8577
  • [8] Synthesis of pyrazolyl-2-pyrazolines by treatment of 3-(3-aryl-3-oxopropenyl)chromen-4-ones with hydrazine and their oxidation to bis(pyrazoles)
    Lévai, A
    Silva, AMS
    Pinto, DCGA
    Cavaleiro, JAS
    Alkorta, I
    Elguero, J
    Jekö, J
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (22) : 4672 - 4679
  • [9] Regioselective epoxidation of 3-(3-oxo-3-arylpropenyl)chromen-4-ones by dimethyldioxirane
    Lévai, A
    Jekö, J
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 2004, 41 (03) : 439 - 441
  • [10] Synthesis of 3-aroyl-4-(3-chromonyl)-2-pyrazolines
    Lévai, A
    Jekö, J
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 2002, 39 (06) : 1333 - 1336
12