I2/DTBP Promoted Synthesis of C3-Carbonylated Imidazopyridines from Chromones and 2-Aminopyridines via (3+2) Cycloaddition

Qiang Huang; Lvjia Wu; Jihai Shi; Jiangdong Li; Wei Lu; Fushan Tang; Lei Zhu; Wenwu Zhong; Changkuo Zhao

doi:10.1055/a-2058-0119

Synthesis, Table of Contents

Synthesis 2023; 55(16): 2570-2580
DOI: 10.1055/a-2058-0119

paper

I₂/DTBP Promoted Synthesis of C3-Carbonylated Imidazopyridines from Chromones and 2-Aminopyridines via (3+2) Cycloaddition

Authors

Qiang Huang

^aSchool of Pharmacy, Zunyi Medical University, Zunyi, Guizhou 563000, P. R. of China

^bThe Key Laboratory of Clinical Pharmacy of Zunyi City, Zunyi Medical University, Zunyi, Guizhou 563006, P. R. of China
Lvjia Wu

^aSchool of Pharmacy, Zunyi Medical University, Zunyi, Guizhou 563000, P. R. of China
Jihai Shi

^aSchool of Pharmacy, Zunyi Medical University, Zunyi, Guizhou 563000, P. R. of China
Jiangdong Li

^cSchool of Public Health, Zunyi Medical University, Zunyi, Guizhou 563000, P. R. of China
Wei Lu

^aSchool of Pharmacy, Zunyi Medical University, Zunyi, Guizhou 563000, P. R. of China
Fushan Tang

^aSchool of Pharmacy, Zunyi Medical University, Zunyi, Guizhou 563000, P. R. of China

^bThe Key Laboratory of Clinical Pharmacy of Zunyi City, Zunyi Medical University, Zunyi, Guizhou 563006, P. R. of China
Lei Zhu

^aSchool of Pharmacy, Zunyi Medical University, Zunyi, Guizhou 563000, P. R. of China

^bThe Key Laboratory of Clinical Pharmacy of Zunyi City, Zunyi Medical University, Zunyi, Guizhou 563006, P. R. of China
Wenwu Zhong∗

^dChongqing Medical and Pharmaceutical College, Chongqing 401331, P. R. of China
Changkuo Zhao∗

^aSchool of Pharmacy, Zunyi Medical University, Zunyi, Guizhou 563000, P. R. of China

Abstract

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Abstract

An I₂/DTBP-promoted (3+2) cycloaddition reaction of 2-aminopyridines and chromones is reported. The work provides a simple and efficient approach to access imidazopyridines scaffold in moderate to good yields. I₂/DTBP as an initiator and oxidant was used to realize the tandem (3+2) cycloaddition/oxidative aromatization. Available starting materials, excellent functional-group tolerance, potential drug activity of the products, and application in production on a gram scale are advantageous features of this strategy. Moreover, the obtained products provide a key active fragment for the synthesis of cabozantinib analogues, which has the potential to be developed as an anticancer agent.

Key words

imidazopyridine - cycloaddition - 2-aminopyridine - chromones - DTBP

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References

References

1a Wang J, Wu H, Song G, Yang D, Huang J, Yao X, Qin H, Chen Z, Xu Z, Xu C. BioMed Res. Int. 2020; 4929053
1b Iqbal MA, Husain A, Alam O, Khan SA, Ahmad A, Haider MR, Alam MA. Arch. Pharm. 2020; 353: e2000071
1c Ramesh V, Rao GP. C. Russ. J. Gen. Chem. 2019; 89: 1491
1d Sayeed IB, Vishnuvardhan M, Nagarajan A, Kantevari S, Kamal A. Bioorg. Chem. 2018; 80: 714
1e He LJ, Yang DL, Chen HY, Huang JH, Zhang YJ, Qin HX, Wang JL, Tang DY, Chen ZZ. OncoTargets Ther. 2020; 13: 10111

2a O’Malley T, Miller MJ, Alling T, Early JV, Wescott HA, Kumar A, Moraski GC, Masquelin T, Hipskind PA, Parish T. Antimicrob. Agents Chemother. 2018; 62: e02439
2b Thakur A, Pereira G, Patel C, Chauhan V, Dhaked RK, Sharma A. J. Mol. Struct. 2020; 1206: 127686
2c Mishra NP, Mohapatra S, Sahoo CR, Raiguru BP, Nayak S, Jena S, Padhy RN. J. Mol. Struct. 2021; 1246: 131183

3a Khatun S, Singh A, Bader GN, Sofi FA. J. Biomol. Struct. Dyn. 2021; 39: 1
3b Rucilova V, Swierczek A, Vanda D, Funk P, Lemrova B, Gawalska A, Bucki A, Nowak B, Zadrozna M, Pociecha K, Soural M, Wyska E, Pawlowski M, Chlon-Rzepa G, Zajdel P. Eur. J. Med. Chem. 2021; 209: 112854
3c Vanda D, Zajdel P, Soural M. Eur. J. Med. Chem. 2019; 181: 111569

4a Lovering F, Aevazelis C, Chang J, Dehnhardt C, Fitz L, Han S, Janz K, Lee J, Kaila N, McDonald J, Moore W, Moretto A, Papaioannou N, Richard D, Ryan MS, Wan ZK, Thorarensen A. ChemMedChem 2016; 11: 217
4b Su JC, Chang CH, Wu SH, Shiau CW. J. Enzyme Inhib. Med. Chem. 2018; 33: 1248
4c Dabiri Y, Gama-Brambila RA, Taskova K, Herold K, Reuter S, Adjaye J, Utikal J, Mrowka R, Wang J, Andrade-Navarro MA, Cheng X. iScience 2019; 12: 168
4d Buonfiglio R, Prati F, Bischetti M, Cavarischia C, Furlotti G, Ombrato R. Molecules 2020; 25: 2163
4e Damghani T, Moosavi F, Khoshneviszadeh M, Mortazavi M, Pirhadi S, Kayani Z, Saso L, Edraki N, Firuzi O. Sci. Rep. 2021; 11: 3644
4f Gu X, Wang Y, Wang M, Wang J, Li N. J. Biomol. Struct. Dyn. 2021; 39: 63

5a Wang Y, Li S, Wang X, Yao Y, Feng L, Ma C. RSC Adv. 2022; 12: 5919
5b Acharya SS, Bhaumick P, Kumar R, Choudhury LH. ACS Omega 2022; 7: 18660
5c Zhang Y, Chen R, Wang Z, Wang L, Ma Y. J. Org. Chem. 2021; 86: 6239
5d Huang L, Yin W, Wang J, Gan C, Huang Y, Huang C, He Y. RSC Adv. 2019; 9: 2381
5e Pandey K, Rangan K, Kumar A. J. Org. Chem. 2018; 83: 8026
5f Iazzetti A, Cacchi S, Ciogli A, Demitri N, Fabrizi G, Ghirga F, Goggiamani A, Lamba D. Synthesis 2018; 50: 3513
5g Hariss L, Hadir KB, El-Masri M, Roisnel T, Gree R, Hachem A. Beilstein J. Org. Chem. 2017; 13: 2115
5h Wan J.-P, Hu D, Liu Y, Li L, Wen C. Tetrahedron Lett. 2016; 57: 2880
5i Cheng C, Ge L, Lu X, Huang J, Huang H, Chen J, Cao W, Wu X. Tetrahedron 2016; 72: 6866
5j Kamal A, Reddy CN, Satyaveni M, Chandrasekhar D, Nanubolu JB, Singarapu KK, Maurya RA. Chem. Commun. 2015; 51: 10475
5k Qian G, Liu B, Tan Q, Zhang S, Xu B. Eur. J. Org. Chem. 2014; 4837
5l Monir K, Kuma Bagdi A, Mishra S, Majee A, Hajra A. Adv. Synth. Catal. 2014; 356: 1105
5m Wang Z, Sun G, Chen W, Zeng X, Wu H, Chen S, Chen Q. Chin. J. Org. Chem. 2021; 41: 3482

6 Stanislas M, Stephan S. WO 2010084425 A1, 2010
7 Reen GK, Kumar A, Sharma P. Beilstein J. Org. Chem. 2019; 15: 1612

8a Wang S, Zhang S, Liu M, Zang J, Jiang G, Ji F. Org. Chem. Front. 2020; 7: 697
8b Tashrifi Z, Mohammadi-Khanaposhtani M, Larijani B, Mahdavi M. Eur. J. Org. Chem. 2020; 269
8c Semwal R, Ravi C, Kumar R, Meena R, Adimurthy S. J. Org. Chem. 2019; 84: 792
8d Jin CA, Xu Q, Feng G, Jin Y, Zhang L. Chin. J. Org. Chem. 2018; 38: 775

9a Reddy KR, Gupta AP, Das P. Asian J. Org. Chem. 2016; 5: 900
9b Sultana F, Shaik SP, Kamal A, Alarifi A, Srivastava AK, Kamal A. Asian J. Org. Chem. 2017; 6: 890

10 Zhan H, Zhao L, Liao J, Li N, Chen Q, Qiu S, Cao H. Adv. Synth. Catal. 2015; 357: 46

11a Dong KK, Huang Q. Tetrahedron Lett. 2019; 60: 1871
11b Kaikai D, Qiang H, Dong Y, Jianxin J, Qiang F. Huaxi Yaoxue Zazhi 2020; 35: 016

12a Xu ZB, Gao YM, Wang SS, Zhang QL, Zhang LZ, Shen L. J. Org. Chem. 2022; 87: 3461
12b Zhang M, Gong Y, Zhou W, Zhou Y, Liu XL. Org. Chem. Front. 2021; 8: 3968

13a Zhang T, Yao W, Wan J.-P, Liu Y. Adv. Synth. Catal. 2021; 363: 4811
13b Guo DG, Wang HJ, Zhou Y, Liu XL. Org. Biomol. Chem. 2022; 20: 4681

14 Li W, Gembreska NR, Vogel AK, Ziegelmeyer EC, Cheng E, Wu F, Roberts LP, Vesoulis MM. Synlett 2020; 32: 539
15 Chen K, Gao B, Shang Y, Du J, Gu Q, Wang J. Org. Biomol. Chem. 2017; 15: 8770

16a Karmacharya U, Guragain D, Chaudhary P, Jee J.-G, Kim J.-A, Jeong B.-S. Int. J. Mol. Sci. 2021; 22: 9685
16b Zhang J, Dai J, Lan X, Zhao Y, Yang F, Zhang H, Tang S, Liang G, Wang X, Tang Q. Eur. J. Med. Chem. 2022; 233: 114215

17 Spadafora M, Postupalenko VY, Shvadchak VV, Klymchenko AS, Mely Y, Burger A, Benhida R. Tetrahedron 2009; 65: 7809
18 Pleier AK, Glas H, Grosche M, Sirsch P, Thiel WR. Synthesis 2001; 55
19 Wan JP, Hu D. q, Liu Y, Li LY, Wen CP. Tetrahedron Lett. 2016; 57: 2880

Supplementary Material

Supporting Information (PDF)