Synthesis 2023; 55(14): 2186-2194
DOI: 10.1055/a-2035-0040
paper

A New Method for the Synthesis of 1-Methyl-1H-indole-3-carboxylate Derivatives, Employing Copper(II)

Ali Akbari
,
Muhammad Saleh Faryabi
We are grateful for the financial support provided by the University of Jiroft for this research, which leads to our exceptional success.


Abstract

We report an efficient method for synthesizing 1-methyl-1H-indole-3-carboxylates by cross-dehydrogenative coupling. However, the coupling reactions are a way to functionalize the α-carbon of iminiums from tertiary amines. The synthesis of 1-methyl-1H-indole-3-carboxylates from N,N-dimethylaniline with bromoacetates has not been reported. In the present work, we describe a novel route for synthesizing 1-methyl-1H-indole-3-carboxylates with N,N-dimethylaniline and a wide range of phenyl bromoacetate derivatives. Features such as a simple procedure and good to excellent yields (69–90%) make this method a highly efficient procedure for the preparation of indole derivatives using Cu(OAc)2·H2O as a catalyst in the presence of tert-butyl hydroperoxide.

Supporting Information



Publikationsverlauf

Eingereicht: 08. Dezember 2022

Angenommen nach Revision: 14. Februar 2023

Accepted Manuscript online:
14. Februar 2023

Artikel online veröffentlicht:
29. März 2023

© 2023. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 
  • References

    • 1a Chen JQ, Li JH, Dong ZB. Adv. Synth. Catal. 2020; 362: 3311
    • 1b Lu F.-D, Chen J, Jiang X, Chen J.-R, Lu L.-Q, Xiao W.-J. Chem. Soc. Rev. 2021; 50: 12808
    • 1c Yoo W.-J, Li C.-J. Cross-Dehydrogenative Coupling Reactions of sp3-Hybridized C–H Bonds. In C-H Activation. Yu J.-Q, Shi Z. Springer; Berlin Heidelberg: 2010: 281
  • 2 Jang Y, Lee SB, Hong J, Chun S, Lee J, Hong S. Org. Biomol. Chem. 2020; 18: 5435
  • 3 Li J, Huang C.-Y, Li C.-J. Trends Chem. 2022; 4: 479
  • 4 Bosque I, Chinchilla R, Gonzalez-Gomez JC, Guijarro D, Alonso F. Org. Chem. Front. 2020; 7: 1717
    • 5a Wang Z.-H, Gao P.-S, Wang X, Gao J.-Q, Xu X.-T, He Z, Ma C, Mei T.-S. J. Am. Chem. Soc. 2021; 143: 15599
    • 5b Tian T, Li Z, Li C.-J. Green Chem. 2021; 23: 6789
  • 6 Jones KM, Klussmann M. Synlett 2012; 23: 159
    • 7a Batra A, Singh KN. Eur. J. Org. Chem. 2020; 6676
    • 7b Peng K, Dong ZB. Adv. Synth. Catal. 2021; 363: 1185
    • 7c Gulzar N, Schweitzer-Chaput B, Klussmann M. Catal. Sci. Technol. 2014; 4: 2778
  • 8 Zhang J, Tiwari B, Xing C, Chen X, Chi YR. Angew. Chem. Int. Ed. 2012; 51: 3649
  • 9 Afsina C, Aneeja T, Neetha M, Anilkumar G. Eur. J. Org. Chem. 2021; 1776
  • 10 Correa A. Ni- and Fe-Based Cross-Coupling Reactions. Springer; 2017
  • 11 Cho SH, Kim JY, Kwak J, Chang S. Chem. Soc. Rev. 2011; 40: 5068
  • 12 Villar-Martínez MD, Moreno-Ajona D, Chan C, Goadsby PJ. Headache 2021; 61: 700
  • 13 Al-Otaibi JS, Mary YS, Mary YS, Yadav R. J. Mol. Struct. 2021; 1245: 131074
  • 14 Scott LJ, Perry CM. Drugs 2000; 60: 1411
  • 15 Jabir NR, Firoz CK, Zughaibi TA, Alsaadi MA, Abuzenadah AM, Al-Asmari AI, Alsaieedi A, Ahmed BA, Ramu AK, Tabrez S. Ann. Med. 2022; 54: 2861
  • 16 Phillips RM. The pharmacological evaluation and development of novel anti-cancer compounds. Doctoral Thesis. University of Huddersfield; UK: 2019
  • 17 Costanzo M, De Giglio MA, Roviello GN. Curr. Med. Chem. 2020; 27: 4536
  • 18 Berdeja JG, Laubach JP, Richter J, Stricker S, Spencer A, Richardson PG, Chari A. Clin. Lymphoma, Myeloma Leuk. 2021; 21: 752
  • 19 Kaur J, Utreja D, Jain N, Sharma S. Curr. Org. Synth. 2019; 16: 17
  • 20 Han Y, Dong W, Guo Q, Li X, Huang L. Eur. J. Med. Chem. 2020; 203: 112506
  • 21 Wan Y, Li Y, Yan C, Yan M, Tang Z. Eur. J. Med. Chem. 2019; 183: 111691
  • 22 Tamura Y, Morita I, Hinata Y, Kojima E, Ozasa H, Ikemoto H, Asano M, Wada T, Hayasaki-Kajiwara Y, Iwasaki T. Bioorg. Med. Chem. Lett. 2022; 68: 128769
  • 23 Borg HM, Kabel A, Abdel-Kareem M. Bull. Egypt. Soc. Physiol. Sci. 2020; 40: 1
  • 25 Singh S, Sharma N, Chandra R. Org. Chem. Front. 2022; 9: 3624
  • 26 George N, Akhtar MJ, Al Balushi KA, Khan SA. Bioorg. Chem. 2022; 105941
  • 27 Chen Y, Li H, Liu J, Zhong R, Li H, Fang S, Liu S, Lin S. Eur. J. Med. Chem. 2021; 226: 113813
  • 28 Zhang S.-S, Tan Q.-W, Guan L.-P. Mini-Rev. Med. Chem. 2021; 21: 2261
    • 29a Chilton WS, Bigwood J, Jensen RE. J. Psychedelic Drugs 1979; 11: 61
    • 29b Herlenius E, Lagercrantz H. Early Hum. Dev. 2001; 65: 21
    • 30a Negård M, Uhlig S, Kauserud H, Andersen T, Høiland K, Vrålstad T. Toxins 2015; 7: 1431
    • 30b Sharma A, Verma P, Mathur A, Mathur AK. Protoplasma 2018; 255: 425
  • 31 Hechhu R, Vasanthi R, Balla TB, Kaliaperumal J. Res. J. Pharm. Technol. 2022; 15: 1653
  • 32 Chiba T, Yamamoto K, Sato S, Suzuki K. Clin. Exp. Gastroenterol. 2013; 123
  • 33 Irving H, Turek I, Kettle C, Yaakob N. Int. J. Mol. Sci. 2021; 22: 11910
  • 34 Israili ZH. Curr. Med. Chem.: Cent. Nerv. Syst. Agents 2001; 1: 171
  • 35 Li Z, Zhao L, Liang L, Zhao L, Li F, Wang C, Li Z. J. Org. Chem. 2021; 86: 1964
  • 36 Li Y, Peng J, Chen X, Mo B, Li X, Sun P, Chen C. J. Org. Chem. 2018; 83: 5288
  • 37 Guo X, Han J, Liu Y, Qin M, Zhang X, Chen B. J. Org. Chem. 2017; 82: 11505
  • 38 Huang F, Wu P, Wang L, Chen J, Sun C, Yu Z. J. Org. Chem. 2014; 79: 10553
  • 39 Neumann JJ, Rakshit S, Dröge T, Würtz S, Glorius F. Chem. Eur. J. 2011; 17: 7298
  • 40 Zhao L, Qiu C, Zhao L, Yin G, Li F, Wang C, Li Z. Org. Biomol. Chem. 2021; 19: 5377
  • 41 Bellavita R, Casertano M, Grasso N, Gillick-Healy M, Kelly BG, Adamo MF, Menna M, Merlino F, Grieco P. Symmetry 2022; 14: 435
  • 42 Tang S, Gao X, Lei A. Chem. Commun. 2017; 53: 3354
  • 43 Liu W.-Q, Lei T, Song Z.-Q, Yang X.-L, Wu C.-J, Jiang X, Chen B, Tung C.-H, Wu L.-Z. Org. Lett. 2017; 19: 3251
  • 44 Wu C.-J, Meng Q.-Y, Lei T, Zhong J.-J, Liu W.-Q, Zhao L.-M, Li Z.-J, Chen B, Tung C.-H, Wu L.-Z. ACS Catal. 2016; 6: 4635
  • 45 Peterson PE, Wolf JP. III, Niemann C. J. Org. Chem. 1958; 23: 303
  • 46 Zhang H, Liu D, Chen C, Liu C, Lei A. Chem. Eur. J. 2011; 17: 9581
  • 47 Lang R, Wu J, Shi L, Xia C, Li F. Chem. Commun. 2011; 47: 12553
  • 48 Lang R, Shi L, Li D, Xia C, Li F. Org. Lett. 2012; 14: 4130
  • 49 Wu J, Lan J, Guo S, You J. Org. Lett. 2014; 16: 5862
  • 50 Qi Z, Li L, Liang Y.-K, Ma A.-J, Zhang X.-Z, Peng J.-B. Org. Lett. 2021; 23: 4769
  • 51 Lian X.-L, Ren Z.-H, Wang Y.-Y, Guan Z.-H. Org. Lett. 2014; 16: 3360
  • 52 Nishino M, Hirano K, Satoh T, Miura M. J. Org. Chem. 2011; 76: 6447
    • 54a Boess E, Schmitz C, Klussmann M. J. Am. Chem. Soc. 2012; 134: 5317
    • 54b Ratnikov MO, Xu X, Doyle MP. J. Am. Chem. Soc. 2013; 135: 9475
    • 54c Vara Y, Aldaba E, Arrieta A, Pizarro JL, Arriortua MI, Cossío FP. Org. Biomol. Chem. 2008; 6: 1763
  • 55 Natelson S, Gottfried S. Org. Synth. 1943; 23: 37
  • 56 Li X, Liang D, Huang W, Zhou H, Li Z, Wang B, Ma Y, Wang H. Tetrahedron 2016; 72: 8442