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

Yurii V. Ostapiuk; Maksym Shehedyn; Oksana V. Barabash; Bohdan Demydchuk; Sviatoslav Batsyts; Colin Herzberger; Andreas Schmidt

doi:10.1055/s-0040-1719849

Synthesis, Table of Contents

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

Authors

Yurii V. Ostapiuk∗

^aIvan Franko National University of Lviv, Department of Organic Chemistry, Kyryla i Mefodiya Str. 6, 79005 Lviv, Ukraine
Maksym Shehedyn

^aIvan Franko National University of Lviv, Department of Organic Chemistry, Kyryla i Mefodiya Str. 6, 79005 Lviv, Ukraine
Oksana V. Barabash

^aIvan Franko National University of Lviv, Department of Organic Chemistry, Kyryla i Mefodiya Str. 6, 79005 Lviv, Ukraine
Bohdan Demydchuk

^bV.P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry NAS of Ukraine, Murmanska Str. 1, 02094 Kyiv-94, Ukraine
Sviatoslav Batsyts

^cClausthal University of Technology, Institute of Organic Chemistry, Leibnizstrasse 6, 38678 Clausthal-Zellerfeld, Germany
Colin Herzberger

^cClausthal University of Technology, Institute of Organic Chemistry, Leibnizstrasse 6, 38678 Clausthal-Zellerfeld, Germany
Andreas Schmidt ∗

^cClausthal University of Technology, Institute of Organic Chemistry, Leibnizstrasse 6, 38678 Clausthal-Zellerfeld, Germany

Abstract

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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.

Key words

Meerwein arylation - arenediazonium salts - 3-hydroxythiophenes - Fiesselmann reaction

Full Text

References

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

34a Mo F, Qiu D, Zhang L, Wang J. Chem. Rev. 2021; 121: 5741
34b Kindt S, Heinrich MR. Synthesis 2016; 48: 1597
34c Baumann M, Baxendale IR. Beilstein J. Org. Chem. 2013; 9: 2265
34d Meerwein H, Büchner E, van Emster K. J. Prakt. Chem. 1939; 152: 237

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

Supplementary Material

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