Synthesis of Functionalized Pyrazolo[1,5-a]pyridines: [3+2] Cycloaddition of N-Aminopyridines and α,β-Unsaturated Carbonyl Compounds/Alkenes at Room Temperature

Chitrakar Ravi; Supravat Samanta; Darapaneni Chandra Mohan; N. Naresh Kumar Reddy; Subbarayappa Adimurthy

doi:10.1055/s-0036-1588753

Synthesis, Table of Contents

Synthesis 2017; 49(11): 2513-2522
DOI: 10.1055/s-0036-1588753

paper

Synthesis of Functionalized Pyrazolo[1,5-a]pyridines: [3+2] Cycloaddition of N-Aminopyridines and α,β-Unsaturated Carbonyl Compounds/Alkenes at Room Temperature

Authors

Chitrakar Ravi

Academy of Scientific & Innovative Research, CSIR–Central Salt & Marine Chemicals Research Institute, G. B. Marg, Bhavnagar–364 002, Gujarat, India Email: adimurthy@csmcri.res.in
Supravat Samanta

Academy of Scientific & Innovative Research, CSIR–Central Salt & Marine Chemicals Research Institute, G. B. Marg, Bhavnagar–364 002, Gujarat, India Email: adimurthy@csmcri.res.in
Darapaneni Chandra Mohan

Academy of Scientific & Innovative Research, CSIR–Central Salt & Marine Chemicals Research Institute, G. B. Marg, Bhavnagar–364 002, Gujarat, India Email: adimurthy@csmcri.res.in
N. Naresh Kumar Reddy

Academy of Scientific & Innovative Research, CSIR–Central Salt & Marine Chemicals Research Institute, G. B. Marg, Bhavnagar–364 002, Gujarat, India Email: adimurthy@csmcri.res.in
Subbarayappa Adimurthy*

Academy of Scientific & Innovative Research, CSIR–Central Salt & Marine Chemicals Research Institute, G. B. Marg, Bhavnagar–364 002, Gujarat, India Email: adimurthy@csmcri.res.in

Abstract

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Abstract

The synthesis of functionalized pyrazolo[1,5-a]pyridines through oxidative [3+2] cycloaddition of N-aminopyridines with α,β-unsaturated carbonyl compounds or electron-withdrawing olefins is described. The reactions proceed in N-methylpyrrolidone as the solvent under metal-free conditions at room temperature.

Key words

N-methylpyrrolidone - chalcones - metal-free - drug intermediates - [3+2] cycloaddition

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References

References

1a Guo X.-X, Gu D.-W, Wu Z, Zhang W. Chem. Rev. 2015; 115: 1622-1622
1b Marina JD. P, Diogo LP, Manuel MB. M. Eur. J. Org. Chem. 2015; 33: 7197-7197

2a Joule JA, Mills K. Heterocyclic Chemistry . 4th ed. Blackwell; Oxford: 1990
2b Michael JP. Nat. Prod. Rep. 2005; 22: 627-627

For recent reviews on the chemistry and properties of pyrazoles, see:

2c Janin YL. Chem. Rev. 2012; 112: 3924-3924
2d Fustero S, Sánchez-Roselló M, Barrio P, Simón-Fuentes A. Chem. Rev. 2011; 111: 6984-6984
2e Schmidt A, Dreger A. Curr. Org. Chem. 2011; 15: 1423-1423
2f Yoon J.-Y, Lee S.-g, Shin H. Curr. Org. Chem. 2011; 15: 657-657
2g Fustero S, Simón-Fuentes A, Sanz-Cervera JF. Org. Prep. Proced. Int. 2009; 41: 253-253
2h Seung HC, Ji YK, Jaesung K, Sukbok C. Chem. Soc. Rev. 2011; 40: 4879-4879
2i Nicolaou KC, Rao PB, Hao J, Reddy MV, Rassias G, Huang X, Chen D.-K, Snyder SA. Angew. Chem. Int. Ed. 2003; 42: 1753-1753

3 Hansen BJ, Weis J, Suzdak PD, Eskesen K. Bioorg. Med. Chem. Lett. 1994; 4: 695-695
4 Stevens KL, Jung DK, Alberti MJ, Badiang JG, Peckham GE, Veal JM, Cheung MP, Harris AS, Chamberlain D, Peel MR. Org. Lett. 2005; 7: 4753-4753

5a Löber S, Hübner H, Utz W, Gmeiner P. J. Med. Chem. 2001; 44: 2691-2691
5b Bettinetti L, Schlotter K, Hübner H, Gmeiner P. J. Med. Chem. 2002; 45: 4594-4594
5c Löber S, Aboul-Fadl T, Hübner H, Gmeiner P. Bioorg. Med. Chem. Lett. 2002; 12: 633-633
5d Löber S, Ortner B, Bettinetti L, Hübner H, Gmeiner P. Tetrahedron: Asymmetry 2002; 13: 2296-2296
5e Boeckler F, Russig H, Zhang WN, Löber S, Schetz J, Hübner H, Ferger B, Gmeiner P, Feldon J. Psychopharmacology 2004; 175: 331-331
5f Bettinetti L, Hübner H, Gmeiner P. Arch. Pharm. 2005; 338: 276-276
5g Prante O, Hocke C, Löber S, Hübner H, Gmeiner P, Kuwert T. Nuklearmed. 2006; 45: 235-235
5h Lysenkova LN, Turchin KF, Danilenko VN, Korolev AM, Preobrazhenskaya MN. J. Antibiot. 2010; 63: 17-17

6 Zoni-Berisso M, Lercari F, Carazza T, Domenicucci S. Clin. Epidemiol. 2014; 6: 213-213
7 Aboul-Fadl T, Löber S, Gmeiner P. Synthesis 2000; 1727-1727

8a Yokoe I, Matsumoto S, Shirataki Y, Komatsu M. Heterocycles 1985; 23: 1395-1395
8b Harada N, Nakanishi K. J. Chem. Soc. D 1970; 310-310
8c Tamura Y, Tsujimoto N, Sumida Y, Ikeda M. Tetrahedron 1972; 28: 21-21
8d Potts KT, Youzwak HP, Zurawel SJ. Jr. J. Org. Chem. 1980; 45: 90-90
8e Tominaga Y, Ichihara Y, Mori T, Kamio C, Hosomi A. J. Heterocycl. Chem. 1990; 27: 263-263

9a Wu HC, Hwang LC, Wu MJ. Org. Biomol. Chem. 2011; 9: 670-670
9b Ling L, Chen J, Song J, Zhang Y, Li X, Song L, Shi F, Li Y, Wu C. Org. Biomol. Chem. 2013; 11: 3894-3894
9c Chen Z, Gao L, Ye S, Ding Q, Wu J. Chem. Commun. 2012; 48: 3975-3975
9d Ding S, Yan Y, Jiao N. Chem. Commun. 2013; 49: 4250-4250

10a Mousseau JJ, Bull JA, Ladd CL, Fortier A, Roman DS, Charette AB. J. Org. Chem. 2011; 76: 8243-8243
10b Mousseau JJ, Fortier A, Charette AB. Org. Lett. 2010; 12: 516-516

11 Wu H.-C, Yang C.-W, Hwang L.-C, Wu M.-J. Org. Biomol. Chem. 2012; 10: 6640-6640

12a Huang P, Yang Q, Chen Z, Ding Q, Xu J, Peng Y. J. Org. Chem. 2012; 77: 8092-8092
12b Chen Z, Wu J. Org. Lett. 2012; 14: 5385-5385

13a Zhao J, Wu C, Li P, Ai W, Chen H, Wang C, Larock RC, Shi F. J. Org. Chem. 2011; 76: 6837-6837
13b Zhao J, Li P, Wu C, Chen H, Ai W, Sun R, Ren H, Larock RC, Shi F. Org. Biomol. Chem. 2012; 10: 1922-1922
13c Ravi C, Mohan DC, Reddy NN. K, Adimurthy S. RSC Adv. 2015; 5: 42961-42961
13d Tao W, Ailong S, Haiyan F, Shuwu Y, Meng G, Jun T, Lei A. Tetrahedron 2015; 71: 4473-4473

14 Chen Z, Wu J. Org. Lett. 2010; 12: 4856-4856
15 Ou Y, Jiao N. Chem. Commun. 2013; 49: 3473-3473
16 Zheng QZ, Feng P, Liang YF, Jiao N. Org. Lett. 2013; 15: 4202-4202

17a Xie F, Qi Z, Li X. Angew. Chem. Int. Ed. 2013; 52: 11862-11862
17b Boekelheide V, Lehn WL. J. Org. Chem. 1961; 26: 428-428

18 Stevens KL, Jung DK, Alberti MJ, Badiang JG, Peckham GE, Veal JM, Cheung M, Harris PA, Chamberlain SD, Peel MR. Org. Lett. 2005; 7: 4653-4653

19a Fustero S, Román R, Asensio A, Maestro MA, Aceña JL, Simón-Fuentes A. Eur. J. Org. Chem. 2013; 7164-7164
19b Kendall JD, Marshall AJ, Giddens AC, Tsang KY, Boyd M, Frédérick R, Lill CL, Lee W.-J, Kolekar S, Chao M, Malik A, Yu S, Chaussade C, Buchanan CM, Rewcastle GW, Baguley BC, Flanagan JU, Denny WA, Shepherd PR. Med. Chem. Commun. 2014; 5: 41-41

20a Yan R, Luo J, Wang C, Ma CW, Huang G, Liang Y.-M. J. Org. Chem. 2010; 75: 5395-5395
20b Bethel PA, Campbell AD, Goldberg FW, Kemmitt PD, Lamont GM, Suleman A. Tetrahedron 2012; 68: 5434-5434
20c Deng X, Liang JT, Peterson M, Rynberg R, Cheung E, Mani NS. J. Org. Chem. 2010; 75: 1940-1940
20d Takahashi Y, Hibi S, Hoshino Y, Kikuchi K, Shin K, Murata-Tai K, Fujisawa M, Ino M, Shibata H, Yonaga M. J. Med. Chem. 2012; 55: 5255-5255
20e Liu C, Lu Q, Huang Z, Zhang J, Liao F, Peng P, Lei A. Org. Lett. 2015; 17: 6034-6034
20f Jawaid A, Nepal D, Park K, Jespersen M, Qualley A, Mirau P, Drummy LF, Vaia RA. Chem. Mater. 2016; 28: 337-337

21a Mohan DC, Ravi C, Rao SN, Adimurthy S. Org. Biomol. Chem. 2015; 13: 3556-3556
21b Chunavala KC, Joshi G, Suresh E, Adimurthy S. Synthesis 2011; 635-635

22 Patnaik S, Dietz HC, Zheng W, Austin C, Marugan JJ. J. Org. Chem. 2009; 74: 8870-8870

23a Gmeiner P, Schunemann J. Arch. Pharm. 1988; 321: 517-517
23b Ibaraki YS, Hyogo AA, Nishinomiya HK, Ashiya TM. US Patent 5338743, 1994

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