Synthesis 2022; 54(03): 732-740
DOI: 10.1055/s-0040-1719849
paper

Bromoarylation of Methyl 2-Chloroacrylate under Meerwein Conditions for the Synthesis of Substituted 3-Hydroxythiophenes

Yurii V. Ostapiuk
a   Ivan Franko National University of Lviv, Department of Organic Chemistry, Kyryla i Mefodiya Str. 6, 79005 Lviv, Ukraine
,
Maksym Shehedyn
a   Ivan Franko National University of Lviv, Department of Organic Chemistry, Kyryla i Mefodiya Str. 6, 79005 Lviv, Ukraine
,
Oksana V. Barabash
a   Ivan Franko National University of Lviv, Department of Organic Chemistry, Kyryla i Mefodiya Str. 6, 79005 Lviv, Ukraine
,
Bohdan Demydchuk
b   V.P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry NAS of Ukraine, Murmanska Str. 1, 02094 Kyiv-94, Ukraine
,
Sviatoslav Batsyts
c   Clausthal University of Technology, Institute of Organic Chemistry, Leibnizstrasse 6, 38678 Clausthal-Zellerfeld, Germany
,
Colin Herzberger
c   Clausthal University of Technology, Institute of Organic Chemistry, Leibnizstrasse 6, 38678 Clausthal-Zellerfeld, Germany
,
c   Clausthal University of Technology, Institute of Organic Chemistry, Leibnizstrasse 6, 38678 Clausthal-Zellerfeld, Germany
› Author Affiliations


Abstract

Methyl 3-aryl-2-bromo-2-chloropropanoates can be prepared by Meerwein reaction from methyl 2-chloroacrylate and various arenediazonium salts under copper(II) bromide catalysis. The resulting readily available compounds were used as starting materials in reactions with substituted methanethiols for the construction of substituted 3-hydroxythiophenes which have not yet been accessible by other routes. Structural variety of the obtained 2-substituted 5-aryl-3-hydroxythiophenes has been achieved due to a wide range of available starting materials, including both anilines and thiols.

Supporting Information



Publication History

Received: 10 August 2021

Accepted after revision: 30 September 2021

Article published online:
05 November 2021

© 2021. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 
  • References

    • 1a Joule JA. Prog. Heterocycl. Chem. 2020; 31: 177
    • 1b Schatz J. In Science of Synthesis, Vol. 9. Maas G. Thieme; Stuttgart: 2001: 287
    • 1c Rudorf W.-D. In Houben–Weyl, Vol. E6a. Kreher RP. Thieme; Stuttgart: 1994: 186
    • 2a Shah R, Verma PK. Chem. Cent. J. 2018; 12: 137
    • 2b Mishra R, Kumar N, Mishra I, Sachan N. Mini-Rev. Med. Chem. 2020; 20: 1944
    • 2c Dighe NS, Balsane AS, Laware RB, Dengale SS, Sane GS, Musmade DS. Am. J. PharmTech Res. 2014; 4: 91
  • 3 Barbarella G, Zangoli M, Di Maria F. Adv. Heterocycl. Chem. 2017; 123: 105
    • 4a Wilson DP, Wan Z.-K, Xu W.-X, Kirincich SJ, Follows BC, Joseph-McCarthy D, Foreman K, Moretto A, Wu J, Zhu M, Binnun E, Zhang Y.-L, Tam M, Erbe DV, Tobin J, Xu X, Leung L, Shilling A, Tam SY, Mansour TS, Lee J. J. Med. Chem. 2007; 50: 4681
    • 4b Wan Z.-K, Lee J, Hotchandani R, Moretto A, Binnun E, Wilson DP, Kirincich SJ, Follows BC, Ipek M, Xu W, Joseph-McCarthy D, Zhang Y.-L, Tam M, Erbe DV, Tobin JF, Li W, Tam SY, Mansour TS, Wu J. ChemMedChem 2008; 3: 1525
  • 5 Volynets G, Lukashov S, Borysenko I, Gryshchenko A, Starosyla S, Bdzhola V, Ruban T, Iatsyshyna A, Lukash L, Bilokin Y, Yarmoluk S. Monatsh. Chem. 2019; 150: 1801
  • 6 Gargano EM, Perspicace E, Hanke N, Carotti A, Marchais-Oberwinkler S, Hartmann RW. Eur. J. Med. Chem. 2014; 87: 203
  • 7 Hansen FK, Khankischpur M, Tolaymat I, Mesaros R, Dannhardt G, Geffken D. Bioorg. Med. Chem. Lett. 2012; 22: 5031
  • 8 Hu D, Yang C, Lok C.-N, Xing F, Lee P.-Y, Fung YM. E, Jiang H, Che C.-M. Angew. Chem. Int. Ed. 2019; 58: 10914
    • 9a Rackham MD, Brannigan JA, Rangachari K, Meister S, Wilkinson AJ, Holder AA, Leatherbarrow RJ, Tate EW. J. Med. Chem. 2014; 57: 2773
    • 9b Wright MH, Clough B, Rackham MD, Rangachari K, Brannigan JA, Grainger M, Moss DK, Bottrill AR, Heal WP, Broncel M, Serwa RA, Brady D, Mann DJ, Leatherbarrow RJ, Tewari R, Wilkinson AJ, Holder AA, Tate EW. Nat. Chem. 2014; 6: 112
  • 10 Cleghorn LA. T, Ray PC, Odingo J, Kumar A, Wescott H, Korkegian A, Masquelin T, Lopez Moure A, Wilson C, Davis S, Huggett M, Turner P, Smith A, Epemolu O, Zuccotto F, Riley J, Scullion P, Shishikura Y, Ferguson L, Rullas J, Guijarro L, Read KD, Green SR, Hipskind P, Parish T, Wyatt PG. J. Med. Chem. 2018; 61: 6592
  • 11 Hegde G, Murausky AA, Murauski AA, Kukhta IN, Adhikari AV, Komitov L. RSC Adv. 2015; 5: 79800
  • 12 Gerwien A, Reinhardt T, Mayer P, Dube H. Org. Lett. 2018; 20: 232
  • 13 Sassi M, Salamone MM, Ruffo R, Patriarca GE, Mari CM, Pagani GA, Posset U, Beverina L. Adv. Funct. Mater. 2016; 26: 5240
  • 14 Hao Y, Chen Y. Dyes Pigm. 2016; 129: 186
    • 15a Hossan AS. M. Text. Res. J. 2020; 90: 376
    • 15b Abomelha H. Pigm. Resin Technol. 2019; 48: 337
  • 16 Kostyuchenko AS, Yurpalov VL, Kurowska A, Domagala W, Pron A, Fisyuk AS. Beilstein J. Org. Chem. 2014; 10: 1596
  • 17 Irgashev RA, Steparuk AS, Rusinov GL. Org. Biomol. Chem. 2018; 16: 4821
    • 18a Demina NS, Kazin NA, Rasputin NA, Irgashev RA, Rusinov GL. Beilstein J. Org. Chem. 2019; 15: 2678
    • 18b Demina NS, Rasputin NA, Irgashev RA, Tameev AR, Nekrasova NV, Rusinov GL, Nunzi J.-M, Charushin VN. ACS Omega 2020; 5: 9377
  • 19 Friedländer P. Ber. Dtsch. Chem. Ges. 1906; 39: 1060
  • 20 Friedlaender P, Kielbasinski St. Ber. Dtsch. Chem. Ges. 1912; 45: 3389
  • 21 Gabrieli S, Cirilli R, Benincori T, Pierini M, Rizzo S, Rossi S. Eur. J. Org. Chem. 2017; 861
  • 22 Hergué N, Frère P, Roncalli J. Org. Biomol. Chem. 2011; 9: 588
    • 23a Hunter GA, McNab H, Withell K. Synthesis 2010; 1707
    • 23b Fiesselmann H, Thoma F. Chem. Ber. 1956; 89: 1907
    • 23c Corral C, Lissavetzky J, Manzanares I. J. Heterocycl. Chem. 1990; 27: 315
    • 23d Hunter GA, McNab H. J. Chem. Soc., Perkin Trans. 1 1995; 1209
    • 23e Hedegaard B, Mortensen JZ, Lawesson SO. Tetrahedron 1971; 27: 3853
    • 24a Sato Y, Onozaki Y, Sugimoto T, Kurihara H, Kamijo K, Kadowaki C, Tsujino T, Watanabe A, Otsuki S, Mitsuya M, Iida M, Haze K, Machida T, Nakatsuru Y, Komatani H, Kotani H, Iwasawa Y. Bioorg. Med. Chem. Lett. 2009; 19: 4673
    • 24b Larsson E. J. Prakt. Chem. 1983; 325: 328
    • 25a Fabbro C, Armani S, Carloni L.-E, De Leo F, Wouters J, Bonifazi D. Eur. J. Org. Chem. 2014; 5487
    • 25b Rangnekar DW, Mavlankar SV. J. Heterocycl. Chem. 1991; 28: 1449
  • 26 Acharya A, Gautam V, Ila H. J. Org. Chem. 2017; 82: 7920
  • 27 Wu J, Xu K, Hirao H, Yoshikai N. Chem. Eur. J. 2017; 23: 1521
    • 28a Mummel S, Lederle F, Hübner EG, Namyslo JC, Nieger M, Schmidt A. Angew. Chem. Int. Ed. 2021; 60: 18882
    • 28b Schmidt A, Snovydovych B, Hemmen S. Eur. J. Org. Chem. 2008; 4313
    • 28c Schmidt A, Mordhorst T. Synthesis 2005; 781
    • 28d Schmidt A, Mordhorst T, Habeck T. Org. Lett. 2002; 4: 1375
    • 28e Schmidt A, Kindermann MK. J. Org. Chem. 1998; 63: 4636
    • 28f Schmidt A, Kindermann MK. J. Org. Chem. 1997; 62: 3910
    • 29a Pruschinski L, Lücke A.-L, Freese T, Kahnert S.-R, Mummel S, Schmidt A. Synthesis 2020; 52: 882
    • 29b Lücke A.-L, Wiechmann S, Freese T, Guan Z, Schmidt A. Z. Naturforsch., B 2016; 71: 643
    • 29c Lücke A.-L, Wiechmann S, Freese T, Schmidt A. Synlett 2017; 28: 1990
    • 29d Rahimi A, Namyslo JC, Drafz M, Halm J, Hübner EG, Nieger M, Rautzenberg N, Schmidt A. J. Org. Chem. 2011; 76: 7316
  • 30 Batsyts S, Shehedyn M, Goreshnik EA, Obushak MD, Schmidt A, Ostapiuk YV. Eur. J. Org. Chem. 2019; 7842
    • 31a Ostapiuk YV, Obushak MD, Matiychuk VS, Naskrent M, Gzella AK. Tetrahedron Lett. 2012; 53: 543
    • 31b Matiychuk VS, Martyak RL, Obushak ND, Ostapiuk YV, Pidlypniyi NI. Chem. Heterocycl. Compd. 2004; 40: 1218
    • 31c Bazel Y, Tupys A, Ostapiuk Y, Tymoshuk O, Imrich J, Šandrejová J. RSC Adv. 2018; 8: 15940
  • 32 Forti L, Ghelfi F, Pagnoni UM. Tetrahedron Lett. 1995; 36: 3023
  • 33 Pastushak N. J. Org. Chem. USSR 1965; 1: 1907 ; Zh. Org. Khim. 1965, 1, 1875
  • 35 Sundberg RJ, Hong J, Smith SQ, Sabat M, Tabakovic I. Tetrahedron 1998; 54: 6259
  • 36 Hansch C, Leo A, Taft RW. Chem. Rev. 1991; 91: 165
  • 37 Hunter GA, McNab H. New J. Chem. 2010; 34: 2558
  • 38 Ishizaki M, Kitajima T. Jpn. Kokai Tokkyo Koho JP 06025222A, 1994
  • 39 Orofiamma B, Silvestre L, Souhami E. PCT Int. Appl WO 2009138195A2, 2009
  • 40 Nobeshima H, Kitajima T. Jpn. Kokai Tokkyo Koho JP 08176141A, 1996
  • 41 Ishizaki M, Osada S, Kato S. Jpn. Kokai Tokkyo Koho JP 02172986A, 1990
  • 42 Guo M, Zhang H, Zhang Z, Su Z. Zhiwu Ziyuan Yu Huanjing 1996; 5: 53
  • 43 Ishizaki M, Kitajima T, Osada S, Kato T. Jpn. Kokai Tokkyo Koho JP 05078348A, 1993
  • 44 Barker JM, Huddleston PR, Wood ML. J. Chem. Res., Synop. 1992; 291
  • 45 Bertram HJ, Luerssen K, Santel J, Schmidt RR, Plant A, Krueger BW, Harder A, Mencke N. Ger. Offen DE 4111652A1, 1992