Efficient Synthesis of Conjugated 1,3,4-Thiadiazole Hybrids through Palladium-Catalyzed Cross-Coupling of 2,5-Bis(4-bromophenyl)-1,3,4-thiadiazole with Boronic Acids

Monika Wróblowska; Agnieszka Kudelko; Mieczysław Łapkowski

doi:10.1055/s-0034-1378826

Synlett, Table of Contents

Synlett 2015; 26(15): 2127-2130
DOI: 10.1055/s-0034-1378826

letter

Efficient Synthesis of Conjugated 1,3,4-Thiadiazole Hybrids through Palladium-Catalyzed Cross-Coupling of 2,5-Bis(4-bromophenyl)-1,3,4-thiadiazole with Boronic Acids

Monika Wróblowska

^aDepartment of Chemical Organic Technology and Petrochemistry, The Silesian University of Technology, Krzywoustego 4, 44100 Gliwice, Poland Email: Agnieszka.Kudelko@polsl.pl

,

Agnieszka Kudelko*

^aDepartment of Chemical Organic Technology and Petrochemistry, The Silesian University of Technology, Krzywoustego 4, 44100 Gliwice, Poland Email: Agnieszka.Kudelko@polsl.pl

,

Mieczysław Łapkowski

^bDepartment of Physical Chemistry and Technology of Polymers, The Silesian University of Technology, Strzody 9, 44100 Gliwice, Poland

^cCentre of Polymer and Carbon Materials of the Polish Academy of Sciences, M. Curie-Sklodowskiej 34, 41-819 Zabrze, Poland

› Author Affiliations

Abstract

All articles of this category

Abstract

New derivatives of 2,5-bis(4-heteroarylphenyl)-1,3,4-thiadiazole were synthesized under Suzuki cross-coupling reactions from 2,5-bis(4-bromophenyl)-1,3,4-thiadiazole and commercially available boronic acids. Reactions were conducted in a two-phase solvent system in the presence of catalytic amounts of tetrakis(triphenylphosphine)palladium(0), cesium carbonate as a base, and tetrabutylammonium bromide playing a role of a phase-transfer catalyst.

Key words

heterocycles - cross-coupling - phase-transfer catalysis - palladium - catalysis

Full Text

References

References and Notes

1a Hu Y, Li C, Wang X, Yang Y, Zhu H. Chem. Rev. 2014; 114: 5572
1b Haider S, Alam MS, Hamid H. Eur. J. Med. Chem. 2015; 92: 156
1c Tambe SM, Tasaganva RG, Inamdar SR, Kariduraganavar MY. J. Appl. Polym. Sci. 2012; 125: 1049

2a Sharma B, Verma A, Prajapati S, Sharma UK. Int. J. Med. Chem. 2013; 1
2b Shrivastava K, Purohit S, Singhal S, Pradesh U, Pradesh M. Asian J. Biomed. Pharm. Sci. 2013; 3: 6

3a Kraft A, Grimsdale AC, Holmes AB. Angew. Chem. Int. Ed. 1998; 37: 402
3b Segura JL. Acta Polym. 1998; 49: 319
3c Mitschke U, Bauerle P. J. Mater. Chem. 2000; 10: 1471

4a Schulz B, Bruma M, Brehmer L. Adv. Mater. 1997; 9: 601
4b Thelakkat M, Schmidt HW. Polym. Adv. Technol. 1998; 9: 429

5a Adachi C, Tsutsui T, Saito S. Appl. Phys. Lett. 1989; 55: 1489
5b Adachi C, Tsutsui T, Saito S. Appl. Phys. Lett. 1990; 56: 799

6 Wang C, Jung GY, Hua Y, Pearson C, Bryce MR, Petty MC, Batsanov AS, Goeta AE, Howard JA. K. Chem. Mater. 2001; 13: 1167

7a Kim DU, Aminaka E, Tsutsui T, Saito S. Jpn. J. Appl. Phys., Part 1 1995; 34: 6255
7b Kim DU, Tsutsui T. Mol. Cryst., Liq. Cryst. Sci. Technol., Sect. A 1996; 280: 325

8 Grykien R, Luszczynska B, Glowacki I, Kurach E, Rybakiewicz R, Kotwica K, Zagorska M, Pron A, Tassini P, Maglione MG, Del Mauro AD. G, Fasolino T, Rega R, Pandolfi G, Minarini C, Aprano S. Opt. Mater. (Amsterdam, Neth.) 2014; 37: 193

9a Wang C, Jung GY, Batsanov AS, Bryce MR, Petty MC. J. Mater. Chem. 2002; 12: 173
9b Waskiewicz K, Gabański R, Żak J, Suwiński J. Electrochem. Solid-State Lett. 2005; 8: E24
9c Fuks-Janczarek I, Reshak AH, Kuźnik N, Kityk IV, Gabański R, Łapkowski M, Motyka R, Suwiński J. Spectrochim. Acta, Part A 2009; 72: 394
9d Łapkowski M, Motyka R, Suwiński J, Data P. Macromol. Chem. Phys. 2012; 231: 29
9e Data P, Łapkowski M, Motyka R, Suwiński J. Electrochem. Acta 2012; 59: 567

10a Schulz B, Orgzall I, Freydank A, Xii C. Adv. Colloid Interface Sci. 2005; 116: 143
10b Chen ZK, Meng H, Lai YH, Huang W. Macromolecules 1999; 32: 4351
10c Tamoto N, Adachi C, Nagai K. Chem. Mater. 1997; 9: 1077
10d Sinigersky V, Wegner G, Schopov I. Eur. Polym. J. 1993; 29: 617

11a Dimitrowa K, Hauschild J, Zaschke H, Schubert H. J. Prakt. Chem. (Leipzig) 1980; 322: 933
11b Lin K.-T, Kuo H.-M, Sheu H.-S, Lai CK. Tetrahedron 2013; 69: 9045
11c Morikawa H, Tomishima M, Kayakiri N, Araki T, Barrett D, Akamatsu S, Matsumoto S, Uchida S, Nakai T, Takeda S, Maki K. Bioorg. Med. Chem. Lett. 2014; 24: 1172

12a Thomsen I, Pedersen U, Rasmussen PB, Yde B, Andersen TP, Lawesson S.-O. Chem. Lett. 1983; 12: 809
12b Deng H, Bernier SG, Doyle E, Lorusso J, Morgan BA, Westlin WF, Evindar G. ACS Med. Chem. Lett. 2013; 4: 942
12c Deokar H, Chaskar J, Chaskar A. J. Heterocycl. Chem. 2014; 51: 719

13a Linganna N, Lokanatha Rai KM. Synth. Commun. 1998; 28: 461
13b Swapna M, Premakumari C, Reddy SN, Padmaja A, Padmavathi V, Kondaiah P, Krishna NS. Chem. Pharm. Bull. 2013; 61: 722
13c Muralikrishna A, Mallikarjuna Reddy G, Lavanya G, Padmavathi V, Padmaja A. J. Heterocycl. Chem. 2014; 51: 179

14a Yella R, Khatun N, Rout SK, Patel BK. Org. Biomol. Chem. 2011; 9: 3235
14b Kashtoh H, Hussain S, Khan A, Saad SM, Khan JA. J, Khan KM, Perveen S, Choudhary MI. Bioorg. Med. Chem. 2014; 22: 5454

15a Remers WA, Gibs GJ, Weiss MJ. J. Heterocycl. Chem. 1969; 6: 835
15b Yu P, Hu J, Wan R, Li X, Zheng S, Xu Y. J. Chem. Res. 2014; 38: 347
15c Abdel-Aziem A. J. Heterocycl. Chem. 2015; 52: 251

16 Kudelko A, Wróblowska M. Tetrahedron Lett. 2014; 55: 3252

17a Kudelko A, Jasiak K. Synthesis 2013; 45: 1950
17b Kudelko A, Jasiak K, Ejsmont K. Monatsh. Chem. 2015; 146: 303

18a Suzuki A. Metal-Catalyzed Cross-Coupling Reactions. Diederich F, Stang PJ. Wiley-VCH; Weinheim: 1998. Chap. 2
18b Suzuki A. J. Organomet. Chem. 2002; 653: 83

19 Kudelko A, Wróblowska M, Jarosz T, Łaba K, Łapkowski M. ARKIVOC 2015; (v): 287
20 Siegrist AE, Maeder E, Dunnenberger M, Liechti P. GB 899842, 1962 ; Chem. Abstr. 1962, 57, 13767
21 Representative Procedure for Suzuki Coupling 2,5-Bis(4-bromophenyl)-1,3,4-thiadiazole (3, 0.40 g, 1.00 mmol), the appropriate boronic acid (2.50 mmol), tetrakis(triphenylphosphine)palladium(0) (0.06 g, 0.05 mmol), TBAB (0.03 g, 0.10 mmol), and Cs₂CO₃ (3.26 g, 10.00 mmol) were treated with a combination of toluene (10 mL), H₂O (6 mL), and EtOH (3 mL). The mixture was heated to 80 °C (oil bath) for 2–6 h (TLC monitoring). After cooling, CHCl₃ (200 mL) was added and the mixture filtered through silica gel (20 mL). The filtrate was separated, the organic layer was dried over MgSO₄ and then concentrated on a rotary evaporator. The residue was treated with a mixture of benzene–EtOAc (3:1). The solid precipitate was filtered off, washed with benzene–EtOAc (3:1) and air-dried to give the pure 2,5-disubstituted 1,3,4-thiadiazole. 3,5-Bis(4-biphenylyl)-1,3,4-thiadiazole (5a) White-pearl solid (0.34 g, 92% yield); mp 296–298 °C (lit.¹⁶ 294–296 °C). ¹H NMR (400 MHz, CDCl₃): δ = 7.41 (t, J = 7.6 Hz, 1 H), 7.49 (t, J = 7.6 Hz, 2 H), 7.66 (d, J = 7.6 Hz, 2 H), 7.74 (d, J = 8.4 Hz, 2 H), 8.11 (d, J = 8.4 Hz, 2 H). ¹³C NMR (400 MHz, CDCl₃): δ = 124.4, 127.1, 127.8, 128.1, 128.4, 129.0, 139.9, 143.9, 167.8. UV/Vis: λ_max (CHCl₃) 335.0 nm (ε · 10^–3 60.3 cm^–1 M^–1). IR (ATR): ν = 3060, 3037, 2162, 1946, 1821, 1675, 1604, 1561, 1488, 1451, 1432, 1420, 1401, 1316, 1253, 1185, 1170, 1100, 1040, 1027, 1005, 997, 988, 910, 838, 760,718, 684 cm^–1. Anal. Calcd for C₂₆H₁₈N₂S: C, 79.97; H, 4.65; N, 7.17. Found: C, 79.99; H, 4.63; N, 7.21. HRMS: m/z calcd for [C₂₆H₁₈N₂S + H⁺]: 391.1269; found: 391.1267.

Supplementary Material

Supporting Information