Design and Synthesis of Novel Functionalized Fused Oxazepine and Diazepine Analogues Containing Coumarin Backbone through Domino Reaction

被引:7
作者
Poursan, Samane [1 ]
Ahadi, Somayeh [1 ]
Balalaie, Saeed [1 ,2 ]
Rominger, Frank [3 ]
Bijanzadeh, Hamid Reza [4 ]
机构
[1] KN Toosi Univ Technol, Peptide Chem Res Ctr, POB 15875-4416, Tehran, Iran
[2] Kermanshah Univ Med Sci, Med Biol Res Ctr, Kermanshah, Iran
[3] Heidelberg Univ, Organ Chem Inst, Neuenheimer Feld 270, D-69120 Heidelberg, Germany
[4] Tarbiat Modares Univ, Fac Nat Resources & Marine Sci, Dept Environm Sci, Tehran, Iran
来源
CHEMISTRYSELECT | 2019年 / 4卷 / 20期
基金
美国国家科学基金会;
关键词
Benzodiazepine; Benzoxazepine; 4-Chloro-3-formyl coumarin; Domino reaction; Synthetic methods; ONE-POT SYNTHESIS; EFFICIENT SYNTHESIS; PHARMACOLOGICAL EVALUATION; MULTICOMPONENT REACTIONS; ANTIMICROBIAL ACTIVITY; 3-COMPONENT REACTION; DIRECT ACCESS; IN-VITRO; DERIVATIVES; INHIBITORS;
D O I
10.1002/slct.201900918
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A simple and straightforward approach has been developed for the synthesis of functionalized fused oxazepine and diazepine analogues containing coumarin backbone. The approach was done through three-component reaction of 4-chloro-3-formylcoumarin, triphenyl-lambda(5)-phosphanylidene derivatives and 2-aminophenol or o-phenylenediamine derivatives in the presence of cesium carbonate at room temperature. Carrying out the same reaction without base led to 4-aminoarylcoumarins. Mild reaction conditions and synthesis of fused functionalized heterocyclic backbones are advantages of this approach.
引用
收藏
页码:6403 / 6407
页数:5
相关论文
共 66 条
  • [1] Novel and efficient catalysts for the one-pot synthesis of 3,4-dihydropyrano[c]chromene derivatives in aqueous media
    Abdolmohammadi, Shahrzad
    Balalaie, Saeed
    [J]. TETRAHEDRON LETTERS, 2007, 48 (18) : 3299 - 3303
  • [2] Synthesis of Chromeno[4′,3′:4,5]pyrido[1,2-a]pyrazines and -diazepines by the Reaction of Substituted 2-(3-Acetyl-2-oxo-2H-chromen-4-yl)fumarates with 1, n-Diamines
    Alizadeh, Abdolali
    Jamal, Parinaz
    [J]. SYNLETT, 2018, 29 (08) : 1107 - 1111
  • [3] Catalyst-Free Synthesis of Fused Triazolo-Diazepino[5,6-b]Quinoline Derivatives via a Sequential Ugi-4CR-Nucleophilic Substitution-Intramolecular Click Reaction
    Balalaie, Saeed
    Vaezghaemi, Aref
    Zarezadeh, Nahid
    Rominger, Frank
    Bijanzadeh, Hamid Reza
    [J]. SYNLETT, 2018, 29 (08) : 1095 - 1101
  • [4] Diastereoselective Synthesis of Functionalized Diketopiperazines through Post-transformational Reactions
    Balalaie, Saeed
    Kejani, Reihaneh Ramezani
    Ghabraie, Elmira
    Darvish, Fatemeh
    Rominger, Frank
    Hamdan, Fatima
    Bijanzadeh, Hamid Reza
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (23) : 12141 - 12152
  • [5] Indium-Catalyzed Intramolecular Hydroamidation of Alkynes: An Exo-Dig Cyclization for the Synthesis of Pyranoquinolines through Post-Transformational Reaction
    Balalaie, Saeed
    Mirzaie, Sattar
    Nikbakht, Ali
    Hamdan, Fatima
    Rominger, Frank
    Navari, Razieh
    Bijanzadeh, Hamid Reza
    [J]. ORGANIC LETTERS, 2017, 19 (22) : 6124 - 6127
  • [6] Direct access to isoxazolino and isoxazolo benzazepines from 2-((hydroxyimino) methyl) benzoic acid via a post-Ugi heteroannulation
    Balalaie, Saeed
    Shamakli, Mohammad
    Nikbakht, Ali
    Alavijeh, Nahid S.
    Rominger, Frank
    Rostamizadeh, Shahnaz
    Bijanzadeh, Hamid Reza
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (27) : 5737 - 5742
  • [7] Unusual Acid- and Base-Catalyzed C-N Bond Formation Approach through Reaction of Chromonyl Meldrum's Acid and Nitrogen Binucleophiles
    Balalaie, Saeed
    Bijanzadeh, Hamid Reza
    Mehrparvar, Saber
    Rominger, Frank
    [J]. SYNLETT, 2016, 27 (05) : 782 - 788
  • [8] Novel synthesis of 3,4-dihydro-5-bromo[1,4]oxazin-2-one derivatives, new protease inhibitor scaffold
    Bihel, F
    Kraus, JL
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2003, 1 (05) : 793 - 799
  • [9] Efficient synthesis of chromonylpyrano[c]coumarin, chromonylbenzo[b]pyran, and pyrano[d]pyrimidine in aqueous media
    Bijanzadeh, Hamid Reza
    Mehrparvar, Saber
    Balalaie, Saeed
    [J]. JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2015, 12 (10) : 1859 - 1865
  • [10] Antiproliferative and Differentiating Activities of a Novel Series of Histone Deacetylase Inhibitors
    Binaschi, Monica
    Boldetti, Andrea
    Gianni, Maurizio
    Maggi, Carlo Alberto
    Gensini, Martina
    Bigioni, Mario
    Parlani, Massimo
    Giolitti, Alessandro
    Fratelli, Maddalena
    Valli, Claudia
    Terao, Mineko
    Garattini, Enrico
    [J]. ACS MEDICINAL CHEMISTRY LETTERS, 2010, 1 (08): : 411 - 415