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Synthesis 2019; 51(09): 2023-2029
DOI: 10.1055/s-0037-1612101
DOI: 10.1055/s-0037-1612101
paper
One-Pot Three-Component Strategy for Polysubstituted 2-Aminothiazoles via Ring Opening of α-Nitro Epoxides
This project was supported by the Natural Science Foundation of Zhejiang Province [LY16H300001 (G. Zhang), LY18H300001 (W. Chen)], the National Natural Science Foundation of China (81473074 and 81673291) and the Osteoporosis & Breast Cancer Research Center, USA (Y. Yu).Further Information
Publication History
Received: 28 October 2018
Accepted after revision: 28 December 2018
Publication Date:
18 February 2019 (online)
Abstract
Polysubstituted 2-aminothiazoles have been synthesized via a one-pot three-component reaction of α-nitro epoxides, potassium thiocyanate, and primary amines without the need for any additives. This reaction proceeds smoothly in a highly efficient and eco-friendly manner with good to excellent yields. A possible mechanism is also proposed.
Key words
2-aminothiazoles - nitro epoxides - potassium thiocyanate - primary amines - one-pot synthesisSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1612101.
- Supporting Information
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References
- 1a Das J, Chen P, Norris D, Padmanabha R, Lin J, Moquin RV, Shen Z, Cook LS, Doweyko AM, Pitt S, Pang S, Shen DR, Fang Q. J. Med. Chem. 2006; 49: 6819
- 1b Smith B, Chang HH, Medda F, Gokhale V, Dietrich J, Davis A, Meuillet E, Hulme C. Bioorg. Med. Chem. Lett. 2012; 22: 3567
- 1c Kim KS, Kimball SD, Misra RN, Rawlins DB, Hunt JT, Xiao HY. J. Med. Chem. 2002; 45: 3905
- 1d Misra RN, Xiao HY, Kim KS, Lu S, Han WC, Barbosa SA. J. Med. Chem. 2004; 47: 1719
- 2a Satoh A, Nagatomi Y, Hirata Y, Ito S, Suzuki G, Kimura T, Maehara S, Hikichi H, Satow A, Hata M, Ohta H, Kawamoto H. Bioorg. Med. Chem. 2009; 19: 5464
- 2b Siddiqui N, Arshad MF, Khan SA. Acta Pol. Pharm. 2009; 66: 161
- 2c Siddiqui N, Ahsan W. Eur. J. Med. Chem. 2010; 45: 1536
- 2d Siddiqui N, Ahsan W. Med. Chem. Res. 2011; 20: 261
- 3a Iino T, Tsukahara D, Kamata K, Sasaki K, Ohyama S, Hosaka H, Hasegawa T, Chiba M, Nagata Y, Eiki J, Nishimura T. Bioorg. Med. Chem. 2009; 17: 2733
- 3b Iino T, Hashimoto N, Sasaki K, Ohyama S, Yoshimoto R, Hosaka H, Hasegawa T, Chiba M, Nagata Y, Nishimura JE. T. Bioorg. Med. Chem. 2009; 17: 3800
- 3c Li F, Zhu Q, Zhang Y, Feng Y, Leng Y, Zhang A. Bioorg. Med. Chem. 2010; 18: 3875
- 4a Kalkhambkar RG, Kulkarni GM, Shivkumar H, Rao RN. Eur. J. Med. Chem. 2007; 42: 1272
- 4b Singh N, Bhati SK, Kumar A. Eur. J. Med. Chem. 2008; 43: 2597
- 4c Kouatly O, Geronikaki A, Kamoutsis C, Hadjipavlou-Litina D, Eleftheriou P. Eur. J. Med. Chem. 2009; 44: 1198
- 4d Giri RS, Thaker HM, Giordano T, Williams J, Rogers D, Sudersanam V, Vasu KK. Eur. J. Med. Chem. 2009; 44: 2184
- 5a Chimenti F, Bizzarri B, Maccioni E, Secci D, Bolasco A, Fioravanti R, Chimenti P, Granese A, Carradori S, Rivanera D, Lilli D, Zicari A, Distinto S. Bioorg. Med. Chem. Lett. 2007; 17: 4635
- 5b Roy KK, Singh S, Sharma SK, Srivastava R, Chaturvedi V, Saxena AK. Bioorg. Med. Chem. Lett. 2011; 21: 5589
- 6 Yu H, Shao L, Fang J. J. Organomet. Chem. 2007; 692: 991
- 7 Metwally MA, Metwally A, Abdel-Galil E, Amer FA. Monatsh. Chem. 2008; 139: 35
- 8 Cui Y, Qian G, Chen L, Wang Z, Wang M. Dyes Pigm. 2008; 77: 217
- 9 Misra A, Shahid M, Srivastava P. Thin Solid Films 2010; 519: 1235
- 10 Hantzsch A, Weber JH. Ber. Dtsch. Chem. Ges. 1887; 20: 3118
- 11 Tang X, Zhu Z, Qi C, Wu W, Jiang H. Org. Lett. 2016; 18: 180
- 12 Pradip KS, Chandrasekhar A, Sridhar S, Javed I. Tetrahedron 2008; 49: 11074
- 13 Vidal-Albalat A, Rodríguez S, Gonzalez FV. Org. Lett. 2014; 16: 1752
- 14a Nosood YL, Halimehjani AZ, González FV. J. Org. Chem. 2018; 83: 1252
- 14b Weiß KM, Wei S, Tsogoeva SB. Org. Biomol. Chem. 2011; 9: 3457
- 14c Ibrahim MM, Grau D, Hampel F, Tsogoeva SB. Eur. J. Org. Chem. 2014; 7: 1401
- 14d Guo X, Shao J, Liu H, Chen B, Chen W, Yu Y. RSC Adv. 2015; 5: 51559
- 15a Sprang CA, Degering EF. J. Am. Chem. Soc. 1942; 64: 1063
- 15b Anderson JC, Blake AJ, Mills M, Ratcliffe PD. Org. Lett. 2008; 10: 4141
- 15c Zhao D, Guo S, Guo X, Zhang G, Yu Y. Tetrahedron 2016; 72: 5285