Sulfur-Promoted Redox Cyclization of 2,2′-Dinitrodiphenyl Disulfides and Benzylamines

Abstract

This study aims to develop green and sustainable advanced synthetic methods based on redox cyclization. Elemental sulfur is shown to promote the efficient synthesis of 2-substituted benzothiazoles from 2,2′-dinitrodiphenyl disulfides and benzylamines via redox cyclization in the absence of transition-metal catalysts and solvents. The 2-substituted benzothiazoles are obtained in good to excellent yields. This synthetic methodology is highly atom-economical and does not require any external oxidizing and/or reducing agents.

Key words

redox cyclization - benzothiazoles - 2,2′-dinitrodiphenyl disulfides - benzylamines - elemental sulfur - atom-economical

Publication History

Received: 20 February 2021

Accepted after revision: 12 March 2021

Accepted Manuscript online:
12 March 2021

Article published online:
01 April 2021

• References

• 1a Ram VJ, Sethi A, Nath M, Pratap R. The Chemistry of Heterocycles . Elsevier; Amsterdam: 2017. 149
• 1b Mondal J, Sreejith S, Borah P, Zhao Y. ACS Sustainable Chem. Eng. 2014; 2: 934
• 1c Behrsing HP, Furniss MJ, Davis M, Tomaszewski JE, Parchment RE. Toxicol. Sci. 2013; 131: 470
• 2 Biancalana M, Koide S. Biochim. Biophys. Acta Proteins Proteomics 2010; 1804: 1405
• 3 Sakai J, Miura I, Shibata M, Yonekura N, Hiyoshi H, Takagaki M, Nagayama K. J. Pestic. Sci. 2010; 35: 488
• 4a Wang S, Bao G, Lu Z, Wu P, Han Z. J. Mater. Sci. 2000; 35: 5873
• 4b Fratini AV, Cross EM, O’Brien JF, Adams WW. J. Macromol. Sci., Part B: Phys. 1985; 24: 159
• 4c Yabuki K, Kato K. Sen’i Gakkaishi 1996; 52: 143
• 5 Nguyen TB, Ermolenko L, Retailleau P, Al-Mourabit A. Angew. Chem. Int. Ed. 2014; 53: 13808
• 6 Xing Q, Ma Y, Xie H, Xiao F, Zhang F, Deng G.-J. J. Org. Chem. 2019; 84: 1238
• 7 Pham HT, Ho TH, Do DQ, Nguyen KL. H, Nguyen TT, Phan NT. S. Synlett 2020; 31: 1813
• 8 Teramoto M, Imoto M, Takeda M, Mizuno T, Nomoto A, Ogawa A. J. Org. Chem. 2020; 85: 15213
• 9 Nguyen TB, Ermolenko L, Corbin M, Al-Mourabit A. Org. Chem. Front. 2014; 1: 1157

For recent related sulfur-promoted heterocycle synthesis, see:
• 10a Liu S, Deng G.-J, Huang H. Synlett 2021; 32: 142
• 10b Nguyen TB. Adv. Synth. Catal. 2020; 362: 3448
• 10c Nguyen TB. Adv. Synth. Catal. 2017; 359: 1066
• 10d Nguyen TB. Asian J. Org. Chem. 2017; 6: 477
• 10e Nguyen LA, Ngo QA, Retailleau P, Nguyen TB. Green Chem. 2017; 19: 4289
• 10f Nguyen TB, Ermolenko L, Al-Mourabit A. Org. Lett. 2013; 15: 4218
• 11 Nguyen TB, Ermolenko L, Dean WA, Al-Mourabit A. Org. Lett. 2012; 14: 5948
• 12 Che X, Jiang J, Xiao F, Huang H, Deng G.-J. Org. Lett. 2017; 19: 4576
• 13 Zhang J, Zhao X, Liu P, Sun P. J. Org. Chem. 2019; 84: 12596
• 14 Bogert MT, Stull A. Org. Synth. Coll. Vol. 1 1941; 220
• 15 Downer-Riley NK, Jackson YA. Tetrahedron 2008; 64: 7741
• 16 Huang J, Chan J, Chen Y, Borths CJ, Baucom KD, Larsen RD, Faul MM. J. Am. Chem. Soc. 2010; 132: 3674
• 17 Kumar A, Maurya RA, Saxena D. Mol. Diversity 2010; 14: 331
• 18 Inamoto K, Hasegawa C, Hiroya K, Doi T. Org. Lett. 2008; 10: 5147
• 19 Hachiya H, Hirano K, Satoh T, Miura M. Org. Lett. 2009; 11: 1737
• 20 Yoshino K, Kohno T, Uno T, Morita T, Tsukamoto G. J. Med. Chem. 1986; 29: 820
• 21 Choi S.-J, Park HJ, Lee SK, Kim SW, Han G, Choo H.-YP. Bioorg. Med. Chem. 2006; 14: 1229
• 22 Stevens MF. G, McCall CJ, Lelieveld P, Alexander P, Richter A, Davies DE. J. Med. Chem. 1994; 37: 1689
• 23 Hori M, Kataoka T, Shimizu H, Imai Y, Fujimura H. Yakugaku Zasshi 1978; 99: 1019
• 24 Okimoto M, Yoshida T, Hoshi M, Hattori K, Komata M, Tomozawa K, Chiba T. Heterocycles 2008; 75: 35