Synthesis 2024; 56(01): 187-192
DOI: 10.1055/a-2183-0324
paper

Novel Synthesis of Pyrido[2,3-b]quinoxaline-3-carboxylate Derivatives via One-Pot Buchwald Amination–Cyclization

Majdi Hajri
a   Laboratory of Physics of Lamellar Materials and Hybrids Nanomaterials, Faculty of Sciences of Bizerte, University of Carthage, Zarzouna 7021, Bizerte, Tunisia
,
Omar Khoumeri
b   Laboratoire de Pharmaco-Chimie Radicalaire, Institut de Chimie Radicalaire ICR, Aix-Marseille Université, CNRS, UMR 7273, Marseille, France
,
Raoudha Abderrahim
a   Laboratory of Physics of Lamellar Materials and Hybrids Nanomaterials, Faculty of Sciences of Bizerte, University of Carthage, Zarzouna 7021, Bizerte, Tunisia
,
Thierry Terme
b   Laboratoire de Pharmaco-Chimie Radicalaire, Institut de Chimie Radicalaire ICR, Aix-Marseille Université, CNRS, UMR 7273, Marseille, France
,
Patrice Vanelle
b   Laboratoire de Pharmaco-Chimie Radicalaire, Institut de Chimie Radicalaire ICR, Aix-Marseille Université, CNRS, UMR 7273, Marseille, France
› Author Affiliations
This work was supported by the Centre National de la Recherche Scientifique and Aix-Marseille Université. We also thank the Ministry of Higher Education of Tunisia for financing this work.


Abstract

A novel series of pyrido[2,3-b]quinoxaline-3-carboxylate derivatives was synthesized in short reaction times and in moderate to good yields by using a palladium catalyst in a one-pot Buchwald amination/cyclization reaction.

Supporting Information



Publication History

Received: 26 June 2023

Accepted after revision: 27 September 2023

Accepted Manuscript online:
27 September 2023

Article published online:
31 October 2023

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  • References

  • 1 Tariq S, Somakala K, Amir M. Eur. J. Med. Chem. 2018; 143: 542
  • 2 Pereira JA, Pessoa AM, Cordeiro MN, Fernandes R, Prudencio C, Noronha JP, Vieira M. Eur. J. Med. Chem. 2015; 97: 664
  • 3 Moloney MG. Nat. Prod. Rep. 2002; 19: 597
    • 4a Ghattass K, El-Sitt S, Zibara K, Rayes S, Haddadin MJ, El-Sabban M, Gali-Muhtasib H. Mol. Cancer 2014; 13: 12
    • 4b Montero V, Montana M, Khoumeri O, Correard F, Esteve M.-A, Vanelle P. Pharmaceuticals 2022; 15: 781
  • 5 Jampilek J. Curr. Med. Chem. 2014; 21: 4347
  • 6 Monge A, Palop JA, Urbasos I, Fernández-Alvarez E. J. Heterocycl. Chem. 1989; 26: 1623
  • 7 Gu W, Wang S, Jin X, Zhang Y, Hua D, Miao T, Tao X, Wang S. Molecules 2017; 22: 1154
  • 8 Carta A, Sanna G, Briguglio I, Madeddu S, Vitale G, Piras S, Corona P, Peana AT, Laurini E, Fermeglia M, Pricl S, Serra A, Carta E, Loddo R, Giliberti G. Eur. J. Med. Chem. 2018; 145: 559
  • 9 Chacón-Vargas KF, Nogueda-Torres B, Sánchez-Torres LE, Suarez-Contreras E, Villalobos-Rocha JC, Torres-Martinez Y, Lara-Ramirez EE, Fiorani G, Krauth-Siegel RL, Bolognesi ML, Monge A, Rivera G. Molecules 2017; 22: 220
  • 10 Ajani OO. Eur. J. Med. Chem. 2014; 85: 688
  • 11 Gao H, Yamasaki EF, Chan KK, Shen LL, Snapka RM. Mol. Pharmacol. 2003; 63: 1382
  • 12 Huang CJ, Lee CL, Yang SH, Chien CC, Huang CC, Yang RN, Chang CC. Biochim. Biophys. Acta 2016; 1862: 1345
  • 13 Kakodkar NC, Peddinti R, Kletzel M, Tian Y, Guerrero LJ, Undevia SD. Geary D, Chlenski A, Yang Q, Salwen HR, Cohn SL. Pediatr. Blood Cancer 2011; 56: 164
  • 14 Chandra Shekhar A, Shanthan Rao P, Narsaiah B, Allanki AD, Sijwali PS. Eur. J. Med. Chem. 2014; 77: 280
  • 15 Hajri M, Esteve MA, Khoumeri O, Abderrahim R, Terme T, Montana M, Vanelle P. Eur. J. Med. Chem. 2016; 124: 959
    • 16a Vanelle P, Maldonado J, Madadi N, Gueiffier A, Teulade J.-C, Chapat J.-P, Crozet MP. Tetrahedron Lett. 1990; 31: 3013
    • 16b Crozet MP, Giraud L, Sabuco J.-F, Vanelle P, Barreau M. Tetrahedron Lett. 1991; 32: 4125
    • 16c Delmas F, Gasquet M, Timon-David P, Madadi N, Vanelle P, Vaille A, Maldonado J. Eur. J. Med. Chem. 1993; 28: 23
    • 16d Amiri-Attou O, Terme T, Vanelle P. Molecules 2005; 10: 545
    • 16e Amiri-Attou O, Terme T, Vanelle P. Synlett 2005; 3047
    • 16f Montana M, Terme T, Vanelle P. Tetrahedron Lett. 2006; 47: 6573
    • 16g Curti C, Laget M, Ortiz Carle A, Gellis A, Vanelle P. Eur. J. Med. Chem. 2007; 42: 880
    • 16h Crozet MD, Botta C, Gasquet M, Curti C, Remusat V, Hutter S, Chapelle O, Azas N, De Meo MP, Vanelle P. Eur. J. Med. Chem. 2009; 44: 653
    • 17a Lin W, Hu X.-X, Han J, Liang G.-B. Tetrahedron 2023; 133: 133206
    • 17b Dai X.-J, Engl O.-D, Leon T, Buchwald S.-L. Angew. Chem. Int. Ed. 2019; 58: 3407
    • 17c Jiang B, Meng F.-F, Liang Q.-J, Xu Y.-H, Loh T.-P. Org. Lett. 2017; 19: 914
    • 17d Broumidis E, Koutentis P.-A. Tetrahedron Lett. 2017; 58: 2661
    • 17e Yamaguchi A, Inuki S, Tokimizu Y, Oishi S, Ohno H. J. Org. Chem. 2020; 85: 2543