Synthesis of 2-Arylbenzothiazole Derivatives Based on Activated Carbon/Oxygen Oxidation Followed by Suzuki–Miyaura Coupling

Abstract

A variety of 2-arylbenzothiazole derivatives were synthesized by the reaction of 2-aminobenzenethiol with substituted benzaldehydes in the presence of activated carbon and molecular oxygen system followed by Suzuki–Miyaura coupling using 2-phenylimidazole–PdCl₂ complex.

Key words

2-arylbenzothiazole - activated carbon - molecular oxygen - Suzuki–Miyaura coupling - 2-phenylimidazole

• References

• 1a Tan BS, Tiong KH, Muruhadas A, Randhawa N, Choo HL, Bradshaw TD, Stevens MF. G, Leong CO. Mol. Cancer Ther. 2011; 10: 1982
• 1b Racane L, Kralj M, Suman L, Stojkovic R, Kulenovic VT, Zamola GK. Bioorg. Med. Chem. 2010; 18: 1038
• 1c Caleta I, Kralj M, Marjanovic M, Bertosa B, Tomic S, Pavlovic G, Pavelic K, Zamola GK. J. Med. Chem. 2009; 52: 1744
• 2a Rajeeva B, Srinivasulu N, Shantakumar S. E-J. Chem. 2009; 6: 775
• 2b Kumbhare RM, Ingle VN. Ind. J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2009; 48: 996
• 2c Murthi Y, Pathak D. J. Pharm. Res. 2008; 7: 153
• 3a Gupta A, Rawat S. J. Chem. Pharm. Res. 2010; 2: 244
• 3b Kaur H, Kumar S, Singh I, Saxena KK, Kumar A. Dig. J. Nanomater. Bios. 2010; 5: 67
• 3c Venkatesh P, Pandeya SN. Int. J. ChemTech. Res. 2009; 1: 1354
• 4a Amnerkar N, Bhusari KP. Eur. J. Med. Chem. 2010; 45: 149
• 4b Sharma P, Pandeya SN, Roy RK, Verma AK, Gupta S. Int. J. ChemTech. Res. 2009; 1: 758
• 4c Siddiqui N, Rana A, Khan S, Haque S, Arshad M, Ahmed S, Ahsan W. Acta Pharm. 2009; 59: 441
• 5a Kok SH. L, Gambari R, Chui CH, Yuen MC. W, Lin E, Wong RS. M, Lau FY, Cheng GY. M, Lam WS, Chan SH, Lam KH, Cheng CH, Lai PB. S, Yu MW. Y, Cheung F, Tang JC. O, Chan AS. C. Bioorg. Med. Chem. 2008; 16: 3626
• 5b Wang M, Gao M, Mock B, Miller K, Sledge G, Hutchins G, Zheng Q. Bioorg. Med. Chem. 2006; 14: 8599
• 5c Hutchinson I, Chua MS, Browne HL, Trapani V, Bradshaw TD, Westwell AD. J. Med. Chem. 2001; 44: 1446
• 6a Sadek B, Tabakha MM. A, Fahelelbom KM. S. Molecules 2011; 16: 9386
• 6b Pal N, Kumar M, Seth G. E-J. Chem. 2011; 8: 1174
• 7a Arora P, Das S, Ranawat MS, Arora N, Gupta MM. J. Chem. Pharm. Res. 2010; 2: 317
• 7b Gawai A, Das S, Nemade M, Wathore S. Asian J. Chem. 2011; 23: 3969
• 8 Yar MH, Ansari ZH. Acta Pol. Pharm. 2009;  66:  387 ; Chem. Abstr. 2010, 153, 530327
• 9 Maharan M, William S, Ramzy F, Sembel A. Molecules 2007; 12: 622
• 10 Sreenivasa M, Jaychand E, Shivakumar B, Jayrajkumar K, Vijaykumar J. Arch. Pharm. Sci. Res. 2009; 1: 150
• 11a Pattan S, Suresh C, Pujar V, Reddy V, Rasal V, Koti B. Ind. J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2005; 44: 2404
• 11b Vazquez GN, Paoli P, Rivera IL, Molina RV, Franco J, Andrade RO, Soto SE, Camici G, Coutino D, Ortiz I, Mayorga K, Diaz H. Bioorg. Med. Chem. 2009; 17: 3332
• 11c Surya KD, Chen LH, Stebbins JL, Machleidt T, Mehan M, Dahl R, Yuan HC, Barile E, Emdadi A, Murphy R, Pellecchia M. Bioorg. Med. Chem. 2009; 17: 2712

For other bioactivity, see:
• 12a Mathis CA, Wang Y, Holt DP, Huang G.-F, Debnath ML, Klunk WE. J. Med. Chem. 2003; 46: 2740
• 12b Henriksen G, Hauser AI, Westwell AD, Yousefi BH, Schwaiger M, Drzezga A, Wester HJ. J. Med. Chem. 2007; 50: 1087
• 12c Cui MC, Li ZJ, Tang RK, Liu BL. Bioorg. Med. Chem. 2010; 14: 1777
• 12d Yadav PS, Devprakash Senthilkumar GP. IJPSR 2011; 3: 1
• 12e Khokra SL, Arora K, Mehta H, Aggarwal A, Yadav M. IJPSR 2011; 2: 1356
• 12f Piscitelli F, Ballatore C, Smith A. Bioorg. Med. Chem. Lett. 2010; 20: 644
• 12g Sheng C, Che X, Wang W, Wang S, Cao Y, Yao J, Miao Z, Zhang W. Eur. J. Med. Chem. 2011; 46: 1706
• 13a Costa SP. G, Batista RM. F, Sousa AM. R. C. Mater. Sci. Forum 2006; 514: 147
• 13b Padalkar VS, Tathe A, Gupta VD, Patil VS, Phatangare K, Sekar N. J. Fluoresc. 2012;  22:  311
• 14a Yu G, Yin S, Liu Y, Shuai Z, Zhu D. J. Am. Chem. Soc. 2003; 125: 14816
• 14b Kuwabara J, Namekawa T, Haga MA, Kanbara T. Dalton Trans. 2012;  41: 44
• 15a Leng W, Zhou Y, Xu Q, Liu J. Macromolecules 2001; 34: 4774
• 15b Batista RM. F, Costa SP. G, Malheiro EL, Belsley M, Raposo MM. M. Tetrahedron 2007; 63: 4258
• 15c Zhao M, Samoc M, Prasad PN. Chem. Mater. 1990; 2: 670
• 15d Costa SP. G, Batista RM, Cardoso P, Belsley M, Raposo MM. M. Eur. J. Org. Chem. 2006; 3938

For other properties in material field, see:
• 16a Dikundwar AG, Dutta GK, Row TN. G, Patil S. Cryst. Growth. Des. 2011; 11: 1615
• 16b Ahmed E, Subramaniyan S, Kim FS, Xin H, Jenekhe SA. Macromolecules 2011; 44: 7207
• 16c Wang H, Chen G, Xu X, Chen H, Ji S. Dyes Pigm. 2010; 86: 238
• 16d Raposo MM. M, Castro MC. R, Fonseca AM. C, Schellenberg P, Belsley M. Tetrahedron 2011; 67: 5189
• 16e Sayama K, Tsukagoshi S, Hara K, Ohga Y, Shinpou A, Abe Y, Suga S, Arakawa H. J. Phys. Chem. B 2002; 106: 1363
• 16f Hrobarikova V, Hrobarik P, Gajdos P, Fitilis I, Fakis M, Persephonis P, Zahradnik P. J. Org. Chem. 2010; 75: 305
• 16g Dalton MJ, Kannan R, Haley JE, He GS, McLean DG, Cooper TM, Prasad PN, Tan LS. Macromolecules 2011; 44: 7194
• 16h Wang G, Pu KY, Zhang X, Li K, Wang L, Cai L, Ding D, Lai YH, Liu B. Chem. Mater. 2011; 23: 4428
• 16i Morales AR, Belfield KD, Hales JM, Stryland EW. V, Hagan DJ. Chem. Mater. 2006; 18: 4972
• 16j Belfield KD, Bondar MV, Frazer A, Morales AR, Kachkovsky OD, Mikhailov I, Masunov AE. M, Przhonska OV. J. Phys. Chem. B 2010; 114: 9313
• 16k Nguyen DM, Wang X, Ahn HY, Rodriguez L, Mikhailo V, Bondar MV, Belfield KD. Appl. Mater. Interfaces 2010; 11: 2978
• 16l Qi J, Han MS, Tung CH. Bioorg. Med. Chem. Lett. 2012; 22: 1747
• 16m Batista RM. F, Costa SP. G, Raposo MM. M. Tetrahedron Lett. 2004; 45: 2825
• 16n Barbarella G, Favaretto L, Sotgiu G, Antolini L, Gigli G, Cingolani R, Bongini A. Chem. Mater. 2001; 13: 4112
• 16o Barbarella G. Chem.–Eur. J. 2002; 8: 5073
• 16p Nah MK, Rho SG, Kim HK, Kang JG. J. Phys. Chem. A 2007; 111: 11437
• 16q Lo KK. W, Li CK, Lau JS. Y. Organometallics 2005; 24: 4594
• 16r Zhang XH, Wong OY, Gao ZQ, Lee CS, Kwong HL, Lee ST, Wu SK. Mater. Sci. Eng. B 2001; 85: 182
• 16s Park MJ, Kwak J, Lee J, Jung IH, Kong H, Lee C, Hwang DH, Shim HK. Macromolecules 2010; 43: 1379
• 17 Hayashi M. Chem. Rec. 2008; 8: 252 ; and references cited therein
• 18 Kawamura K, Haneda S, Gan ZB, Eda K, Hayashi M. Organometallics 2008; 27: 3748
• 19 CCDC 660480 contains supplementary crystallographic data for this paper. These data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; fax: [phone]; E-mail: [e-mail]
• 20 Bahrami K, Khodaei MM, Naali F. J. Org. Chem. 2008; 73: 6835
• 21 Sharghi H, Asemani O. Synth. Commun. 2009; 39: 860
• 22 Boeini HZ, Najafabadi KH. Eur. J. Org. Chem. 2009; 4926

For other methods for the synthesis of benzothiazoles, see:
• 23a Brembilla A, Roizard D, Lochon P. Synth. Commun. 1990; 20: 3379
• 23b Moghaddam FM, Bardajee GR, Ismaili H, Taimoory SM. D. Synth. Commun. 2006; 36: 2543
• 23c Saha D, Adak L, Ranu BC. Tetrahedron Lett. 2010; 51: 5624
• 23d Ranjit S, Liu X. Chem.–Eur. J. 2011; 17: 1105
• 24 Bahrami K, Khodaei MM, Naali F. Synlett 2009; 569
• 25 Jin HL, Cheng TX, Chen JX. Appl. Organomet. Chem. 2011; 25: 238
• 26 Chen L, Yang C, Li S, Qin J. Spectrochim. Acta, Part A 2007; 68: 317
• 27 Costa SP. G, Batista RM. F, Cardoso P, Belsley M, Raposo MM. M. Eur. J. Org. Chem. 2006; 3938