One-Pot Telescoped Synthesis of Thiazole Derivatives from β-Keto Esters and Thioureas Promoted by Tribromoisocyanuric Acid

Vitor S. C. de Andrade; Marcio C. S. de Mattos

doi:10.1055/s-0037-1610243

Synthesis, Table of Contents

Synthesis 2018; 50(24): 4867-4874
DOI: 10.1055/s-0037-1610243

paper

One-Pot Telescoped Synthesis of Thiazole Derivatives from β-Keto Esters and Thioureas Promoted by Tribromoisocyanuric Acid

Vitor S. C. de Andrade

,

Marcio C. S. de Mattos*

Departamento de Química Orgânica, Instituto de Química, Universidade Federal do Rio de Janeiro, CP 68545, Rio de Janeiro 219745-970, Brazil Email: mmattos@iq.ufrj.br

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Abstract

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Dedicated to Prof. W. Bruce Kover on the occasion of his 80^th anniversary

Abstract

A simple and efficient one-pot protocol has been developed for the synthesis of thiazole derivatives from readily available starting materials. Tribromoisocyanuric acid was successfully used for α-monohalogenation of β-keto esters in aqueous medium, which in the presence of thiourea and DABCO produced the corresponding 2-aminothiazoles in up to 87% yield. Extension of the reaction to thioacetamide and o-phenylenediamine led to 2-methylthiazole and quinoxalines, respectively. This approach enables telescoping of the two steps into a single process.

Key words

heterocycles - condensation - thiazole - quinoxaline - green chemistry - tribromoisocyanuric acid - pot-ecomomy - thiourea

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References

References

1a Chhabria MT. Patel S. Modi P. Brahmkshatriya PS. Curr. Top. Med. Chem. 2016; 16: 2841
1b Rouf A. Tanyeli C. Eur. J. Med. Chem. 2015; 97: 911
1c Metwally MA. Abdel-Latif E. Amer FA. Kaupp G. J. Sulfur Chem. 2004; 25: 63
1d Dondoni A. Phosphorus Sulfur Silicon Relat. Elem. 1985; 24: 1

2 Sharma RN. Xavier FP. Vasu KK. Chaturvedi SC. Pancholi SS. J. Enzyme Inhib. Med. Chem. 2009; 24: 890
3 Gu XH. Wan XZ. Jiang B. Bioorg. Med. Chem. Lett. 1999; 9: 569

4a Gomes PA. T. M. Barbosa MO. Santiago EF. Cardoso MV. O. Costa NT. C. Hernandes MZ. Moreira DR. M. Da Silva AC. Dos Santos TA. R. Pereira VR. A. Dos Santos FA. B. Pereira GA. N. Ferreira RS. Leite AC. L. Eur. J. Med. Chem. 2016; 121: 387
4b de Oliveira Filho GB. Cardoso MV. O. Espíndola JW. P. Oliveira e Silva DA. Ferreira RS. Coelho PL. Anjos PS. dos Santos ES. Meira CS. Moreira DR. M. Soares MB. P. Leite AC. L. Eur. J. Med. Chem. 2017; 141: 346

5 Łączkowski KZ. Sałat K. Misiura K. Podkowa A. Malikowska N. J. Enzyme Inhib. Med. Chem. 2016; 3: 1576
6 Bell FW. Cantrell AS. Högberg M. Jaskunas SR. Johansson NG. Jordan CL. Kinnick MD. Lind P. Morin JM. Noréen R. J. Med. Chem. 1995; 38: 4929
7 Li JJ. Heterocyclic Chemistry in Drug Discovery. Wiley; Hoboken: 2013
8 De Souza MV. N. J. Sulfur Chem. 2005; 26: 429
9 Hantzsch A. Weber JH. Ber. Dtsch. Chem. Ges. 1887; 20: 3118

10a Robinson R. J. Chem. Soc. 1909; 95: 2167
10b Gabriel S. Ber. Dtsch. Chem. Ges. 1910; 43: 1283

11 Cook AH. Heilbron I. MacDonald SF. Mahadevan AP. J. Chem. Soc. 1949; 1064

12a Nagarajaiah H. Mishra AK. Moorthy JN. Org. Biomol. Chem. 2016; 14: 4129
12b Khan KM. Ambreen N. Karim A. Saied S. Amyn A. Ahmed A. Perveen S. J. Pharm. Res. 2012; 5: 651

13 Meng G. Wang M. Zheng A. Dou J. Guo Z. Green Chem. Lett. Rev. 2014; 7: 46

14a Zhao R. Gove S. Sundeen JE. Chen BC. Tetrahedron Lett. 2001; 42: 2101
14b Zhu YP. Yuan JJ. Zhao Q. Lian M. Gao QH. Liu MC. Yang Y. Wu AX. Tetrahedron 2012; 68: 173

15a Donohoe TJ. Kabeshov MA. Rathi AH. Smith IE. D. Org. Biomol. Chem. 2012; 10: 1093
15b Ma C. Miao Y. Zhao M. Wu P. Zhou J. Li Z. Xie X. Zhang W. Tetrahedron 2018; 74: 3602

16 Castagnolo D. Pagano M. Bernardini M. Botta M. Synlett 2009; 2093
17 Yadav JS. Reddy BV. S. Rao YG. Narsaiah AV. Tetrahedron Lett. 2008; 49: 2381
18 Zhao D. Guo S. Guo X. Zhang G. Yu Y. Tetrahedron 2016; 72: 5285
19 Lei W.-L. Wang T. Feng K.-W. Wu C.-Z. Liu Q. ACS Catal. 2017; 7: 7941

20a Scalacci N. Pelloja C. Raddi M. Castagnolo D. Synlett 2016; 27: 1883
20b Jalani HB. Pandya AN. Pandya DH. Sharma JA. Sudarsanam V. Vasu KK. Tetrahedron Lett. 2013; 54: 5403
20c Golubev V. Zubkov F. Krasavin M. Tetrahedron Lett. 2013; 54: 4844
20d Tang X. Zhu Z. Qi C. Wu W. Jiang H. Org. Lett. 2016; 18: 180

21 Hayashi Y. Chem. Sci. 2016; 7: 866

For our recent work on trihaloisocyanuric acids, see:

22a Sanabria CM. Costa BB. S. Viana GM. de Aguiar LC. S. de Mattos MC. S. Synthesis 2018; 50: 1359
22b Crespo LT. C. Nogueira GP. de Mattos MC. S. Esteves PM. ARKIVOC 2018; (ii): 205
22c Sanabria CM. do Casal MT. de Souza RB. A. de Aguiar LC. S. de Mattos MC. S. Synthesis 2017; 49: 1648
22d Sindra HC. de Mattos MC. S. J. Braz. Chem. Soc. 2016; 27: 1129
22e de Andrade VS. C. de Mattos MC. S. Synthesis 2016; 48: 1381
22f de Almeida LS. Esteves PM. de Mattos MC. S. Tetrahedron Lett. 2015; 56: 6843

23 For a review on the chemistry of tribromoisocyanuric acid, see: de Almeida LS. Esteves PM. de Mattos MC. S. Curr. Green Chem. 2014; 1: 94
24 de Almeida LS. Esteves PM. de Mattos MC. S. Synlett 2006; 1515
25 Mendonça GF. de Almeida LS. de Mattos MC. S. Esteves PM. Ribeiro RS. Curr. Org. Synth. 2015; 12: 603
26 Tozetti SD. F. de Almeida LS. Esteves PM. de Mattos MC. S. J. Braz. Chem. Soc. 2007; 18: 675
27 Mendonça GF. Sindra HC. de Almeida LS. Esteves PM. de Mattos MC. S. Tetrahedron Lett. 2009; 50: 473
28 For a review on the chemistry of quinoxalines, see: Pereira JA. Pessoa AM. Cordeiro MN. D. S. Fernandes R. Prudêncio C. Noronha JP. Vieira M. Eur. J. Med. Chem. 2015; 97: 664
29 Kumar A. Saxena D. Gupta MK. Green Chem. 2013; 15: 2699
30 Dunn PJ. Chem. Soc. Rev. 2012; 41: 1452
31 Romero-Ortega M. Aviles A. Cruz R. Fuentes A. Gómez RM. Plata A. J. Org. Chem. 2000; 65: 7244
32 Narender M. Reddy MS. Kumar VP. Srinivas B. Sridhar R. Nageswar YV. D. Rao KR. Synthesis 2007; 3469
33 Bhattacharya AK. J. Indian Chem. Soc. 1967; 44: 57
34 Gagiu FI. Farmacia 1966; 14: 21
35 Barton A. Breukelman SP. Kaye PT. Meakins GD. Morgan DJ. J. Chem. Soc., Perkin Trans. 1 1982; 159
36 Platonova OV. Volkova SB. Malin SA. Veretennikov EA. Laskin BM. Malin AS. Russ. J. Appl. Chem. 2008; 81: 513
37 Reddy KH. V. Reddy VP. Shankar J. Madhav B. Kumar BS. P. A. Nageswar YV. D. Tetrahedron Lett. 2011; 52: 2679

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