Ultrasound-Promoted and Base-Mediated Regioselective Bromination of Imidazo[1,2-a]pyridines with Pyridinium Tribromide

Hongmei Jiang; Dingyi Guo; Yixin Zhang; Qin-Peng Shen; Shiyun Tang; Junheng You; Yi Huo; Huixian Wang; Qing-Wen Gui

doi:10.1055/s-0040-1707856

Synthesis, Table of Contents

Synthesis 2020; 52(18): 2713-2720
DOI: 10.1055/s-0040-1707856

paper

Ultrasound-Promoted and Base-Mediated Regioselective Bromination of Imidazo[1,2-a]pyridines with Pyridinium Tribromide

Hongmei Jiang

^aCollege of Science, Hunan Agricultural University, Changsha 410128, P. R. of China Email: gqw1216@hunau.edu.cn Email: gqw1216@163.com

,

Dingyi Guo

^aCollege of Science, Hunan Agricultural University, Changsha 410128, P. R. of China Email: gqw1216@hunau.edu.cn Email: gqw1216@163.com

,

Yixin Zhang

^aCollege of Science, Hunan Agricultural University, Changsha 410128, P. R. of China Email: gqw1216@hunau.edu.cn Email: gqw1216@163.com

,

Qin-Peng Shen

^bChina Yunnan Key Laboratory of Tobacco Chemistry, Research and Development Center, China Tobacco Yunnan Industrial Company, Kunming 650231, P. R. of China

,

Shiyun Tang

^bChina Yunnan Key Laboratory of Tobacco Chemistry, Research and Development Center, China Tobacco Yunnan Industrial Company, Kunming 650231, P. R. of China

,

Junheng You

^bChina Yunnan Key Laboratory of Tobacco Chemistry, Research and Development Center, China Tobacco Yunnan Industrial Company, Kunming 650231, P. R. of China

,

Yi Huo

^cCollege of Nursing, Hunan University of Traditional Chinese Medicine, Changsha 410208, P. R. of China

,

Huixian Wang

^aCollege of Science, Hunan Agricultural University, Changsha 410128, P. R. of China Email: gqw1216@hunau.edu.cn Email: gqw1216@163.com

,

Qing-Wen Gui ∗

^aCollege of Science, Hunan Agricultural University, Changsha 410128, P. R. of China Email: gqw1216@hunau.edu.cn Email: gqw1216@163.com

› Author Affiliations

Abstract

All articles of this category

Abstract

By using pyridinium tribromide as the bromo source, an efficient and practical protocol for the synthesis of C3-brominated imidazo[1,2-a]pyridines through ultrasound-promoted and Na₂CO₃-mediated regioselective bromination of imidazo[1,2-a]pyridines has been developed. This method effectively avoids the use of metal catalysts and harsh reaction conditions, and shows attractive characteristics such as operational simplicity, broad substrate scope with good to excellent yields, ease of scale-up and high energy efficiency.

Key words

bromination - pyridinium tribromide - metal-free synthesis - regioselectivity - imidazopyridines - ultrasonic irradiation - base mediated

Full Text

References

References

1a Bagdi AK, Santra S, Monir K, Hajra A. Chem. Commun. 2015; 51: 1555
1b Rupert KC, Henry JR, Dodd JH, Wadsworth SA, Cavender DE, Olini GC, Fahmy B, Siekieka J. Bioorg. Med. Chem. Lett. 2003; 13: 347
1c Rival Y, Grassy G, Michel G. Chem. Pharm. Bull. 1992; 40: 1170
1d Katsura Y, Nishino S, Inoue Y, Tomoi M, Takasugi H. Chem. Pharm. Bull. 1992; 40: 371
1e Hanson SM, Morlock EV, Satyshur KA, Czajkowski C. J. Med. Chem. 2008; 51: 7243
1f Wiegand MH. Drugs 2008; 68: 2411

2a Kim O, Jeong Y, Lee H, Hong S.-S, Hong S. J. Med. Chem. 2011; 54: 2455
2b Sanger DJ. Behav. Pharmacol. 1995; 6: 116
2c Boggs S, Elitzin VI, Gudmundsson K, Martin MT, Sharp MJ. Org. Process Res. Dev. 2009; 13: 781

3a Feng M.-L, Li S.-Q, He H.-Z, Xi L.-Y, Chen S.-Y, Yu X.-Q. Green Chem. 2019; 21: 1619
3b Jiang H, Dong X, Jin X, Zhu D, Yin R, Yu R, Wan S, Zhang L, Jiang T. Chem. Asian J. 2018; 13: 2009
3c Dharmana T, Swapna M. Pharma Chem. 2017; 9 (11) 35
3d Jadhav SA, Shioorkar MG, Chavan OS, Sarkate AP, Shinde DB. Synth. Commun. 2017; 47: 285
3e Zhou X, Yan H, Ma C, He Y, Li Y, Cao J, Yan R, Huang G. J. Org. Chem. 2016; 81: 25
3f Samanta S, Jana S, Mondal S, Monir K, Chandra SK, Hajra A. Org. Biomol. Chem. 2016; 14: 5073

4a Kumar R, Ravi C, Rawat D, Adimurthy S. Eur. J. Org. Chem. 2018; 1665
4b Marhadour S, Bazin M.-A, Marchand P. Tetrahedron Lett. 2012; 53: 297
4c Cao H, Zhan H, Lin Y, Lin X, Du Z, Jiang H. Org. Lett. 2012; 14: 1688
4d Cao H, Lin Y, Zhan H, Du Z, Liu X, Liang Q.-M, Zhang H. RSC Adv. 2012; 2: 5972

5a Chang Q, Liu Z, Liu P, Sun P. J. Org. Chem. 2017; 82: 5391
5b Liu P, Shen Z, Yuan Y, Sun P. Org. Biomol. Chem. 2016; 14: 6523
5c Pérez VM, Fregoso-López D, Miranda LD. Tetrahedron Lett. 2017; 58: 1326
5d Mondal S, Samanta S, Santra S, Bagdi AK, Hajra A. Adv. Synth. Catal. 2016; 358: 3633
5e Lu S, Zhu X, Li K, Guo Y.-J, Wang M.-D, Zhao X.-M, Hao X.-Q, Song M.-P. J. Org. Chem. 2016; 81: 8370

6a Frett B, McConnell N, Kharbanda A, Naresh G, Rounseville B, Warner C, Chang J, Debolske N, Li H.-y. Tetrahedron 2018; 74: 4592
6b Guo T, Fu X.-H, Zhang M, Li Y.-L, Ma Y.-C. Org. Biomol. Chem. 2019; 17: 3150
6c Shaik SP, Sultana F, Ravikumar A, Sunkari S, Alarifi A, Kamal A. Org. Biomol. Chem. 2017; 15: 7696
6d Wang C, Lei S, Cao H, Qiu S, Liu J, Deng H, Yan C. J. Org. Chem. 2015; 80: 12725

7a Guo Y.-J, Lu S, Tian L.-L, Huang E.-L, Hao X.-Q, Zhu X, Shao T, Song M.-P. J. Org. Chem. 2018; 83: 338
7b Xiao G, Min H, Zheng Z, Deng G, Liang Y. Chin. Chem. Lett. 2018; 29: 1363
7c Ravi C, Mohan DC, Adimurthy S. Org. Biomol. Chem. 2016; 14: 2282
7d Dong D.-Q, Hao S.-H, Yang D.-S, Li L.-X, Wang Z.-L. Eur. J. Org. Chem. 2017; 6576
7e Zhang J.-R, Zhan L.-Z, Wei L, Ning Y.-Y, Zhong X.-L, Lai J.-X, Xu L, Tang R.-Y. Adv. Synth. Catal. 2018; 360: 533
7f Gao Y.-C, Huang Z.-B, Xu L, Li Z.-D, Lai Z.-S, Tang R.-Y. Org. Biomol. Chem. 2019; 17: 2279
7g Zhang J.-R, Liao Y.-Y, Deng J.-C, Feng K.-Y, Zhang M, Ning Y.-Y, Lin Z.-W, Tang R.-Y. Chem. Commun. 2017; 53: 7784

8a Gunaganti N, Kharbanda A, Lakkaniga NR, Zhang L, Cooper R, Li H.-y, Frett B. Chem. Commun. 2018; 54: 12954
8b Mondal S, Samanta S, Jana S, Hajra A. J. Org. Chem. 2017; 82: 4504
8c Chen H, Yi H, Tang Z, Bian C, Zhang H, Lei A. Adv. Synth. Catal. 2018; 360: 3220
8d Zhu W, Ding Y, Bian Z, Xie P, Xu B, Tang Q, Wu W, Zhou A. Adv. Synth. Catal. 2017; 359: 2215
8e Xu X, Chen D, Wang Z.-L. Chin. J. Org. Chem. 2019; 39: 3338
8f Zahra T, Mohammad M.-K, Bagher L, Mohammad M. Eur. J. Org. Chem. 2020; 269

9a Semwal R, Ravi C, Kumar R, Meena R, Adimurthy S. J. Org. Chem. 2019; 84: 792
9b Zhou Z, Yuan Y, Cao Y, Qiao J, Yao A, Zhao J, Zuo W, Chen W, Lei A. Chin. J. Chem. 2019; 37: 611
9c Jian W.-Q, Wang H.-B, Du K.-S, Zhong W.-Q, Huang J.-M. ChemElectroChem 2019; 6: 2733
9d Indukuri DR, Potuganti GR, Alla M. Synlett 2019; 30: 1573
9e Li J, Tang J, Wu Y, He Q, Yu Y. RSC Adv. 2018; 8: 5058
9f Katrun P, Kuhakarn C. Tetrahedron Lett. 2019; 60: 989
9g Yuan Y, Yao A, Zheng Y, Gao M, Zhou Z, Qiao J, Hu J, Ye B, Zhao J, Wen H, Lei A. iScience 2019; 12: 293
9h Lee JH, Jung HI, Kim DY. Synth. Commun. 2020; 50: 197

10a Bliman D, Pettersson M, Bood M, Grøtli M. Tetrahedron Lett. 2014; 55: 2929
10b Saikia I, Borah AJ, Phukan P. Chem. Rev. 2016; 116: 6837

11a Wu C, Lu L.-H, Peng A.-Z, Jia G.-K, Peng C, Cao Z, Tang Z, He W.-M, Xu X. Green Chem. 2018; 20: 3683
11b Brahmachari G, Mandal M, Karmakar I, Nurjamal K, Mandal B. ACS Sustainable Chem. Eng. 2019; 7: 6369
11c Pharande SG, Escobosa AR. C, Gámez-Montaño R. Green Chem. 2017; 19: 1259
11d Banerjee B. Ultrason. Sonochem. 2017; 35: 1

12a Jiang H, Tang X, Xu Z, Wang H, Han K, Yang X, Zhou Y, Feng Y.-L, Gui Q.-W. Org. Biomol. Chem. 2019; 17: 2715
12b Jiang H, Tang X, Liu S, Wang L, Shen H, Yang J, Wang H, Gui Q.-W. Org. Biomol. Chem. 2019; 17: 10223
12c Gui Q.-W, He X, Wang W, Zhou H, Dong Y, Wang N, Tang J.-X, Cao Z, He W.-M. Green Chem. 2020; 22: 118

Supplementary Material

Supporting Information