Synthesis of Spiro Pyrazolone-Oxindole and Bicyclic Pyrazolone Derivatives via Solvent-Dependent Regioselective Aza-1,4/1,6-Michael and Intramolecular Cycloaddition under Catalyst-Free Conditions

Abstract

A solvent-dependent, highly regioselective [3+2]-cyclo­addition reaction of isoxazole-styrenes and azomethine imines under catalyst-free conditions is reported, furnishing a library of pyrazolone–spirooxindole hybrids. Good regioselectivity for the isomeric structures was achieved by the reaction of isoxazole-styrene and azomethine imine in different solvents and temperatures. The developed method was extended for the synthesis of tri-substituted dinitrogen-fused pyrazolones by using a 1,6-Michael addition reaction. Furthermore, the isoxazole moiety was converted into a carboxylic acid as a model study via ring opening.

Key words

spirooxindole-pyrazolone hybrids - bicyclic pyrazolones - isoxazole-styrenes - switchable 1,3-dipolar cycloaddition - solvent-­dependent reactivity - catalyst-free conditions

Publication History

Received: 22 March 2021

Accepted after revision: 12 April 2021

Accepted Manuscript online:
13 April 2021

Article published online:
20 May 2021

• References

• 1a Babu SA, Padmavathi R, Aslam NA, Rajkumar V. Stud. Nat. Prod. Chem. 2015; 46: 227
• 1b Singh GS, Desta ZY. Chem. Rev. 2012; 112: 6104
• 1c Cheng D, Ishihara Y, Tan B, Barbas III CF. ACS Catal. 2014; 4: 743
• 1d Zhou L.-M, Qu R.-Y, Yang G.-F. Expert Opin. Drug Discovery 2020; 15: 603
• 2a Zhao Z, Dai X, Li C, Wang X, Tian J, Feng Y, Xie J, Ma C, Nie Z, Fan P, Qian M, He X, Wu S, Zhang Y, Zheng X. Eur. J. Med. Chem. 2020; 186: 111893
• 2b Mrongovius R, Neugebauer M, Rucker G. Eur. J. Med. Chem. 1984; 19: 161
• 2c Khan MF, Alam MM, Verma G, Akhtar W, Akhter M, Shaquiquzzaman M. Eur. J. Med. Chem. 2016; 120: 170
• 3a Yet L. In Comprehensive Heterocyclic Chemistry III, Vol. 4. Katrizky AR, Ramsden CA, Scriven EF. V, Taylor RJ. K. Elsevier Science; Oxford: 2008: 1
• 3b Radl S. In Comprehensive Heterocyclic Chemistry III, Vol. 12. Katrizky AR, Ramsden CA, Scriven EF. V, Taylor RJ. K. Elsevier Science; Oxford: 2008: 1-75
• 3c Liu S, Bao X, Wang B. Chem. Commun. 2018; 54: 11515
• 4a Pezdirc L, Jovanovski V, Bevk D, Jakše R, Pirc S, Meden A, Stanovnik B, Svete J. Tetrahedron 2005; 61: 3977
• 4b Boyd DB. J. Med. Chem. 1993; 36: 1443
• 4c Kamata M, Yamashita T, Kina A, Tawada M, Endo S, Mizukami A, Sasaki M, Tani A, Nakano Y, Watanabe Y, Furuyama N, Funami M, Amano N, Fukatsu K. Bioorg. Med. Chem. Lett. 2012; 22: 4769
• 4d Yao S, Gallenkamp D, Wölfel K, Lüke B, Schindler M, Scherkenbeck J. Bioorg. Med. Chem. 2011; 19: 4669
• 4e Clark MP, Laughlin SK, Laufersweiler MJ, Bookland RG, Brugel TA, Golebiowski A, Sabat MP, Townes JA, VanRens JC, Djung JF, Natchus MG, De B, Hsieh LC, Xu SC, Walter RL, Mekel MJ, Heitmeyer SA, Brown KK, Juergens K, Taiwo YO, Janusz MJ. J. Med. Chem. 2004; 47: 2724
• 5a Muehlebach M, Boeger M, Cederbaum F, Cornes D, Friedmann AA, Glock J, Niderman T, Stoller A, Wagner T. Bioorg. Med. Chem. 2009; 17: 4241
• 5b Varvounis G, Fiamegos Y, Pilidis G. Adv. Heterocycl. Chem. 2001; 80: 75
• 6a Funken N, Zhang Y.-Q, Gansӓuer A. Chem. Eur. J. 2017; 23: 19
• 6b Engler TA, Chai W, Lynch KO. Jr. Tetrahedron Lett. 1995; 36: 7003
• 6c Zhan G, Du W, Chen Y.-C. Chem. Soc. Rev. 2017; 46: 1675
• 6d Zhou Z, Wang Z.-X, Zhou Y.-C, Xiao W, Ouyang Q, Du W, Chen Y.-C. Nat. Chem. 2017; 9: 590
• 6e Nagaraju S, Liu S, Liu J, Yang S, Liu R, Chen Z, Paplal B, Fang X. Org. Lett. 2019; 21: 10075
• 6f Meng JP, Wang WW, Chen YL, Bera S, Wu J. Org. Chem. Front. 2020; 7: 267
• 6g Chavan SP, Varadwaj GB, Parida KM, Bhanage BM. ChemCatChem 2016; 8: 2649
• 7a Merino P, Tejero T, Díez-Martínez A, Gültekin Z. Eur. J. Org. Chem. 2011; 6567
• 7b Chen YR, Zhan G, Du W, Chen Y.-C. Adv. Synth. Catal. 2016; 358: 3759
• 7c Tong M, Zhang Y, Qin C, Fu Y, Liu Y, Li H, Wang W. Org. Chem. Front. 2018; 5: 2945
• 7d Qiu G, Kuang Y, Wu J. Adv. Synth. Catal. 2014; 356: 3483
• 7e Nájera C, Sansano JM, Yus M. Org. Biomol. Chem. 2015; 13: 8596
• 8a Narayan R, Potowski M, Jia Z.-J, Antonchick AP, Waldmann H. Acc. Chem. Res. 2014; 47: 1296
• 8b Adrio J, Carretero JC. Chem. Commun. 2014; 50: 12434
• 8c Bdiri B, Zhao B.-J, Zhou Z.-M. Tetrahedron: Asymmetry 2017; 28: 876
• 8d Vishwanath M, Sivamuthuraman K, Kesavan V. Chem. Commun. 2016; 52: 12314
• 9a Hong L, Kai M, Wu C, Sun W, Zhu G, Li G, Yao X, Wang R. Chem. Commun. 2013; 49: 6713
• 9b Yin C, Lin L, Zhang D, Feng J, Liu X, Feng X. J. Org. Chem. 2015; 80: 9691
• 9c Zhang D, Zhang D.-M, Xu G.-Y, Sun J.-T. Chin. Chem. Lett. 2015; 26: 301
• 9d Lu Y.-L, Sun J, Jiang Y.-H, Yan C.-G. RSC Adv. 2016; 6: 50471
• 10a Zhang Y, Wei B.-W, Lin H, Zhang L, Liu J.-X, Luo H.-Q, Fan X.-L. Green Chem. 2015; 17: 3266
• 10b Nagaraju S, Satyanarayana N, Paplal B, Vasu AK, Kanvah S, Sridhar B, Sripadi P, Kashinath D. RSC Adv. 2015; 5: 94474
• 10c Lin B, Zhang W.-H, Wang D.-D, Gong Y, Wei Q.-D, Liu X.-L, Feng T.-T, Zhou Y, Yuan W.-C. Tetrahedron 2017; 73: 5176
• 10d Nagaraju S, Sathish K, Satyanarayana N, Paplal B, Kashinath D. J. Heterocycl. Chem. 2020; 57: 469
• 10e Nagaraju S, Satyanarayana N, Paplal B, Vasu AK, Kanvah S, Sridhar B, Sripadi P, Kashinath D. RSC Adv. 2015; 5: 81768
• 10f Zhang C, Han Y, Ye S. Chem. Commun. 2019; 55: 7966
• 11a Chen S, Wang G.-L, Xu S.-W, Tian M.-Y, Zhang M, Liu X.-L, Yuan W.-C. Org. Biomol. Chem. 2019; 17: 6551
• 11b Liu X.-L, Gong Y, Chen S, Zuo X, Yao Z, Zhou Y. Org. Chem. Front. 2019; 6: 1603
• 12 Kartikey KD. D, Reddy MS, Chowhan LR. Tetrahedron Lett. 2020; 61: 152664
• 13 Nagaraju S, Sathish K, Paplal B, Satyanarayana N, Kashinath D. New J. Chem. 2019; 43: 14045