Mn-Catalyzed Ligand-Free One-Pot Synthesis of (E)-6,7-Dihydrodibenzo[b,j][1,7]phenanthrolines and (E)-1,2,3,4-Tetrahydrobenzo[b][1,6]naphthyridines through Dehydrogenative Friedlander Annulation/C(sp3)-H Functionalization

被引:6
|
作者
Nagarajan, Sambavi [1 ]
Fazlur-Rahman, Nawaz Khan [1 ]
机构
[1] Vellore Inst Technol, Sch Adv Sci, Organ & Med Chem Res Lab, Vellore 632014, Tamil Nadu, India
来源
ACS OMEGA | 2024年 / 9卷 / 23期
关键词
DEEP EUTECTIC SOLVENTS; CHOLINE CHLORIDE; QUINOLINE; DNA; DERIVATIVES; ANTICANCER; EFFICIENT; ACIDS; ANTIBACTERIAL; ALCOHOLS;
D O I
10.1021/acsomega.4c00188
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An efficient, MnO2-catalyzed ligand-free synthesis of (E)-6,7-dihydrodibenzo[b,j][1,7]phenanthrolines, 13, and (E)-1,2,3,4-tetrahydrobenzo[b][1,6]naphthyridines, 15, utilizing, 2-amino-5-chloro-benzhydrol, 9, acridinol, 10, or 1-benzyl-4-piperidinol, 14, and benzyl alcohols, 11, is reported. The MnO2-catalyzed dehydrogenative Friedlander annulation utilizing ChCl/p-TSA (DES-1) and subsequent C(sp(3))-H functionalization with TBAB/p-TSA (DES-2) was effected at 100 degrees C. The optimized reaction conditions gave excellent product yields, and the products were evaluated for their by UV absorption and fluorescence emission studies.
引用
收藏
页码:24464 / 24476
页数:13
相关论文
共 8 条
  • [1] Metal-free, one-pot synthesis of 2-styrylquinolines via Friedlander annulation and sp3 C-H activation using 1,3-dimethylurea and L-tartaric acid (3:1) as a deep eutectic solvent
    Satyanarayana, Neeli
    Sathish, Kota
    Nagaraju, Sakkani
    Pawar, Ravinder
    Faizan, Mohmmad
    Arumugavel, Murgan
    Shirisha, Thangellapally
    Kashinath, Dhurke
    NEW JOURNAL OF CHEMISTRY, 2021,
  • [2] Metal-free, one-pot synthesis of 2-styrylquinolines via Friedlander annulation and sp3 C-H activation using 1,3-dimethylurea and L-tartaric acid (3:1) as a deep eutectic solvent
    Satyanarayana, Neeli
    Sathish, Kota
    Nagaraju, Sakkani
    Pawar, Ravinder
    Faizan, Mohmmad
    Arumugavel, Murgan
    Shirisha, Thangellapally
    Kashinath, Dhurke
    NEW JOURNAL OF CHEMISTRY, 2022, 46 (04) : 1637 - 1642
  • [3] p-TsOH-promoted synthesis of (E)-6-phenyl-7-styryl-5,6-dihydrodibenzo[b,h][1,6]naphthyridines via cascade intramolecular aza-Michael addition/Friedlander condensation of 2′-aminochalcones in a SDS/H2O system
    Ravi, Makthala
    Chauhan, Parul
    Singh, Shikha
    Kant, Ruchir
    Yadav, Prem. P.
    RSC ADVANCES, 2016, 6 (54) : 48774 - 48778
  • [4] One-pot B(C6F5)3 catalyzed cascade synthesis of 2-substituted-2,3-dihydroquinazolin-4(1H)-ones
    Shinde, Achut R.
    Mane, Yogesh D.
    Muley, Dnyanoba B.
    SYNTHETIC COMMUNICATIONS, 2020, 50 (01) : 33 - 40
  • [5] B(C6F5)3-Catalyzed One-Pot Tandem Diastereoselective Synthesis of cis-2,3-Disubstituted 1,2,3,4-Tetrahydroquinoxalines and cis-2,4-Disubstituted 2,3,4,5-Tetrahydro-1H-1,5-benzodiazepines
    Luo, Zhenli
    Yang, Ji
    Yao, Zhen
    Yang, Jianbo
    Xu, Lijin
    Shi, Qian
    ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (20) : 3527 - 3534
  • [6] Triazine-fused β-carbolines: a facile three-step, one-pot synthesis of novel 2-alkyl(aryl)amino and 2-dialkylamino-7H-[1,3,5]triazino [1′,2′:1,6]pyrido[3,4-b]indol-4-ones
    Primas, Nicolas
    El-Kashef, Hussein
    Lancelot, Jean-Charles
    Lesnard, Aurelien
    Dodd, Robert H.
    Rault, Sylvain
    ARKIVOC, 2010, : 163 - 176
  • [7] sp3 C-H bond functionalization of methyl n-alkyl ketones [MeCOCnH2n+1 (n=6-8)] as a novel method for the one-pot regioselective synthesis of 'bifunctional alkanes' with remote functional groups
    Akhrem, Irena S.
    Afanas'eva, Lyudmila V.
    Kagramanov, Nikolai D.
    Petrovskii, Pavel V.
    TETRAHEDRON LETTERS, 2012, 53 (32) : 4221 - 4224
  • [8] Solvent-free one-pot synthesis of 4-aryl-3,5-dimethyl-1, 4,7,8-tetra hydrodipyrazolo[3,4-b:4′,3′-e]pyridines using Fe3O4@SiO2@(BuSO3H)3 catalytic Fe3+ system as selective colorimetric
    Ziarani, Ghodsi Mohammadi
    Khademi, Mandieh
    Mohajer, Fatemeh
    Anafcheh, Maryam
    Badiei, Alireza
    Ghasemi, Jahan B.
    RESEARCH ON CHEMICAL INTERMEDIATES, 2022, 48 (05) : 2111 - 2133