Efficient One-Pot Synthesis of 2,4-Disubstituted Thiazoles and Dimeric Thiazoles Directly from Acyl Chlorides and β-Azido Disulfides

Yi Liu; Zhi Li; Yichuan Xie; Peng He; Junfei Qiao; Xinyuan Fan; Yuguo Du

doi:10.1055/s-0036-1590810

Synthesis, Inhaltsverzeichnis

Synthesis 2017; 49(21): 4876-4886
DOI: 10.1055/s-0036-1590810

paper

Efficient One-Pot Synthesis of 2,4-Disubstituted Thiazoles and Dimeric Thiazoles Directly from Acyl Chlorides and β-Azido Disulfides

Yi Liu *

^aSchool of Chemistry and Chemical Engineering, Yantai University, 30 Qingquan Rd, Laishan District, Yantai, 264005, P. R. of China eMail: liuyi@ytu.edu.cn

,

Zhi Li

^aSchool of Chemistry and Chemical Engineering, Yantai University, 30 Qingquan Rd, Laishan District, Yantai, 264005, P. R. of China eMail: liuyi@ytu.edu.cn

,

Yichuan Xie

^aSchool of Chemistry and Chemical Engineering, Yantai University, 30 Qingquan Rd, Laishan District, Yantai, 264005, P. R. of China eMail: liuyi@ytu.edu.cn

,

Peng He

^bState Key Laboratory of Environmental Chemistry and Eco-toxicology, Research Center for Eco-Environmental Sciences, Chinese Academy of Sciences, Beijing 100085, P. R. of China eMail: yuguodu@rcees.ac.cn

,

Junfei Qiao

^bState Key Laboratory of Environmental Chemistry and Eco-toxicology, Research Center for Eco-Environmental Sciences, Chinese Academy of Sciences, Beijing 100085, P. R. of China eMail: yuguodu@rcees.ac.cn

,

Xinyuan Fan

^cInstitute of Advanced Synthesis, Nanjing Tech University, Nanjing, 210009, P. R. of China

,

Yuguo Du*

^bState Key Laboratory of Environmental Chemistry and Eco-toxicology, Research Center for Eco-Environmental Sciences, Chinese Academy of Sciences, Beijing 100085, P. R. of China eMail: yuguodu@rcees.ac.cn

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Abstract

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Abstract

A simple and effective one-pot cascade procedure to provide 2,4-disubstituted thiazoles and symmetrical dimeric thiazoles directly from commercially available acid chlorides and β-azido disulfides in moderate to high yields is described. This cascade transformation consists of disulfide cleavage, thiocarbonylation, phosphine-promoted intramolecular Staudinger/aza-Wittig reaction and dehydrogenation to form the corresponding thiazoles. The application of our methodology is demonstrated by the concise two-step synthesis of anticancer agent SMART and its O-linked dimer in 64% and 46% overall yields, respectively. This directed cascade reaction could be easily handled and scaled up under mild conditions, enabling the construction of focused thiazole derivatives for further pharmacological evaluation.

Key words

one-pot reaction - 2,4-disubstituted thiazole - dimeric thiazole - acid chloride - SMART

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References

1a Jin Z. Nat. Prod. Rep. 2013; 30: 869
1b Davyt D. Serra G. Mar. Drugs 2010; 8: 2755
1c Chen B. Heal W. Five-Membered Rings with Two Heteroatoms, Each with Their Fused Carbocyclic Derivatives. In Comprehensive Heterocyclic Chemistry III. Vol. 4. Katrizky R. Rees CW. Scriven EF. V. Taylor RJ. K. Pergamon; New York: 2008: 635
1d Portmann C. Sieber S. Wirthensohn S. Blom JF. Silva LD. Baudat E. Kaiser M. Brun R. Gademann K. J. Nat. Prod. 2014; 28: 557

2a Lu Y. Li CM. Wang Z. Chen J. Mohler ML. Li W. Dalton JT. Miller DD. J. Med. Chem. 2011; 54: 4678
2b Kamisuki S. Shirakawa T. Kugimiya A. Abu-Elheiga L. Choo HY. P. Yamada K. Shimogawa H. Wakil SJ. Uesugi M. J. Med. Chem. 2011; 54: 4923
2c Tsurumi Y. Ueda H. Hayashi K. Takase S. Nishikawa M. Kiyoto S. Okuhara M. J. Antibiot. 1995; 48: 1066
2d Russell S. Rahmani R. Jones AJ. Newson HL. Neilde K. Cotillo I. Rahmani Khajouei M. Ferrins L. Qureishi S. Nguyen N. Martinez-Martinez MS. Weaver DF. Kaiser M. Riley J. Thomas J. De Rycker M. Read KD. Flematti GR. Ryan E. Tanghe S. Rodriguez A. Charman SA. Kessler A. Avery VM. Baell JB. Piggott MJ. J. Med. Chem. 2016; 59: 9686

For selected reviews, see:

3a Nora De Souza MV. J. Sulfur Chem. 2005; 26: 429
3b Xu ZS. Ye T. Heterocycles in Natural Product Synthesis: Thiazoline and Thiazole and their Derivatives; Chap. 13. Wiley-VCH; Weinheim: 2011
3c Wipf P. Chem. Rev. 1995; 95: 2115
3d Wu YJ. Yang BV. Five-Membered Ring Systems: With N and S (Se, Te) Atoms. In Progress in Heterocyclic Chemistry. Vol. 18. Gribble GW. Joule JA. Elsevier; Oxford: 2009: 220
3e Xavier JB. Fernando A. Mercedes A. Curr. Top. Med. Chem. 2014; 14: 1244

4a Hamada Y. Shibata M. Sugiura T. Kato S. Shioiri T. J. Org. Chem. 1987; 52: 1252
4b Williams DR. Lowder PD. Gu YG. Brooks DA. Tetrahedron Lett. 1997; 38: 331
4c Gordon TD. Singh J. Hansen PE. Morgan BA. Tetrahedron Lett. 1993; 34: 1901

5a Domling A. Beck B. Eichelberger U. Sakamuri S. Menon S. Chen QZ. Lu Y. Wessjohann LA. Angew. Chem. Int. Ed. 2006; 45: 7235
5b Pando O. Dorner S. Preusentanz R. Denkert A. Porzel A. Richter W. Wessjohann L. Org. Lett. 2009; 11: 5567
5c Wu G. Zheng R. Nelson J. Zhang L. Adv. Synth. Catal. 2014; 356: 1229

6a Bräse S. Gil C. Knepper K. Zimmermann V. Angew. Chem. Int. Ed. 2005; 44: 5188
6b Eguchi S. ARKIVOC 2005; (ii): 98

7a Liu Y. Liu J. Qi X.-B. Du Y.-G. J. Org. Chem. 2012; 77: 7108
7b Liu Y. Sun X. Zhang X. Liu J. Du Y.-G. Org. Biomol. Chem. 2014; 12: 8453
7c Sun X. Liu Y. Liu J. Gu GF. Du Y.-G. Org. Biomol. Chem. 2015; 13: 4271

8a Chen J. Forsyth CJ. Org. Lett. 2003; 5: 1281
8b Loos P. Ronco C. Riedrich M. Arndt HD. Eur. J. Org. Chem. 2013; 3290

9 Kazemi M. Shiri L. J. Sulfur Chem. 2015; 36: 613

For selected reviews, see:

10a Bérubé G. Curr. Med. Chem. 2006; 13: 131
10b Lian G. Yu B. Chem. Biodivers. 2010; 7: 2660
10c Bérubé G. Expert Opin. Drug Discovery 2016; 11: 281

11a Vesper A.-R. Lacroix J. C-Gaudreault R. Tajmir-Rihai H.-A. Bérubé G. Steroids 2016; 115: 98
11b Stockwin LH. Han B. Yu SX. Hollingshead MG. ElSohly MA. Gul W. Slade D. Galal AM. Newton DL. Int. J. Cancer 2009; 125: 1266

12a Turan-Zitouni G. Altıntop MD. Özdemir A. Kaplancıklı ZA. Çiftçi GA. Temel HE. Eur. J. Med. Chem. 2016; 107: 288
12b Arafa WA. A. Badry MG. J. Chem. Res. 2016; 40: 385
12c Gomha SM. Abdelrazek FM. Abdelrahman AH. Metz P. Heterocycles 2016; 92: 954
12d Truong T. Alvarado J. Tran LD. Daugulis O. Org. Lett. 2010; 12: 1200
12e Ginidi AR. S. Shaaban MR. Farag AM. Elwahy AH. M. J. Heterocycl. Chem. 2015; 52: 1421

13 Han SY. Kim YA. Tetrahedron 2004; 60: 2447
14 Sivaraman B. Aidhen IS. Eur. J. Org. Chem. 2010; 4991

15a Dawsey AC. Li V. Hamilton KC. Wang J. Williams TJ. Dalton Trans. 2012; 7994
15b Lamb RA. Badart MP. Swaney BE. Gai S. Baird SK. Hawkins BC. Aust. J. Chem. 2015; 68: 1829
15c Femandez X. Dunach E. Tetrahedron: Asymmetry 2001; 12: 1279

16 Lu Y. Li CM. Wang Z. Chen J. Mohler ML. Li W. Dalton JT. Miller DD. J. Med. Chem. 2011; 54: 4678

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