An Acid-Mediated Multicomponent Domino Reaction for the Synthesis of N-Substituted Isoindolinones

This article is dedicated to Prof. H. Ila, JNCASR, Bengaluru on the occasion of her 80^th birthday. CSIR-IICT Communication no. IICT/Pubs./2024/205.

Abstract

A one-pot multicomponent reaction of 2-carboxybenzaldehyde, nitriles/anilines and a nucleophile (N,N-disubstituted anilines) for the synthesis of a range of functionalized N-substituted isoindolinone derivatives is described. This metal-free intramolecular cyclization reaction furnishes the desired products in good to excellent yields. The process is environmentally friendly and offers a sustainable method for synthesizing a diverse library of N-substituted isoindolinone derivatives under acidic conditions. This cascade reaction triggers the formation of a C–C and two C–N bonds involving carbonyl and carboxyl groups in the presence of nitriles/anilines. Additionally, in the absence of a nitrogen source, 3-substituted isobenzofuran-1(3H)-ones are synthesized.

Key words

isoindolinones - isobenzofuranones - domino reaction - multicomponent reaction - atom economy - step economy

Publication History

Received: 13 June 2024

Accepted after revision: 06 August 2024

Accepted Manuscript online:
06 August 2024

Article published online:
19 September 2024

• References

• 1 Gao W, Chen M, Ding Q, Peng Y. Chem. Asian J. 2019; 14: 1306
• 2 Upadhyay SP, Thapa P, Sharma R, Sharma M. Fitoterapia 2020; 146: 104722
• 3 Sorbera LA, Leeson PA, Silvestre J, Castaner J. Drugs Future 2001; 26: 651
• 4 Huskisson EC, Scott J. Rheumatology 1979; 18: 49
• 5 Csende F, Porkolab A, Matiz K, Szabo Z, Csorvassy I, Frank L. Sci. Pharm. 1999; 67: 149
• 6 Savela R, Méndez-Gálvez C. Chem. Eur. J. 2021; 27: 5344
• 7 Deniau E, Enders D. Tetrahedron Lett. 2000; 41: 2347
• 8 Anamimoghadam O, Mumtaz S, Nietsch A, Saya G, Motti CA, Wang J, Junk PC, Qureshi AM, Oelgemöller M. Beilstein J. Org. Chem. 2017; 13: 2833
• 9 Youn SW, Ko TY, Kim YH, Kim YA. Org. Lett. 2018; 20: 7869
• 10 Kumar P, Gupta M, Bahadur V, Parmar VS, Singh BK. Eur. J. Org. Chem. 2018; 1552
• 11 Jing K, Cui P.-C, Wang G.-W. Chem. Commun. 2019; 55: 12551
• 12 Fu L.-Y, Ying J, Qi X, Peng J.-B, Wu X.-F. J. Org. Chem. 2019; 84: 1421
• 13 Bal Reddy C, Ram S, Kumar A, Bharti R, Das P. Chem. Eur. J. 2019; 25: 4067
• 14 Bai X.-F, Mu Q.-C, Xu Z, Yang K.-F, Li L, Zheng Z.-J, Xia C.-G, Xu L.-W. ACS Catal. 2019; 9: 1431
• 15 Zhang Y, Zhu H, Huang Y, Hu Q, He Y, Wen Y, Zhu G. Org. Lett. 2019; 21: 1273
• 16 Wang L, Liu X, Liu J, Shen J, Chen Q, He M. Chem. Asian J. 2018; 13: 765
• 17 Ling F, Li Z, Zheng C, Liu X, Ma C. J. Am. Chem. Soc. 2014; 136: 10914
• 18 Wertjes WC, Wolfe LC, Waller PJ, Kalyani D. Org. Lett. 2013; 15: 5986
• 19 Krishna Y, Tanaka F. Org. Lett. 2021; 23: 1874
• 20 Popovics-Tóth N, Rávai B, Tajti Á, Varga B, Bagi P, Perdih F, Szabó PT, Hackler L, Puskás LG, Bálint E. Org. Biomol. Chem. 2021; 19: 8754
• 21 Yuan S, Wang S, Zhao M, Zhang D, Chen J, Li J.-X, Zhang J, Song Y, Wang J, Yu B. Chin. Chem. Lett. 2020; 31: 349
• 22 Wang L, Chen K, Zhang M, Ye M, Qiao X. Crit. Rev. Biotechnol. 2022; 42: 125
• 23 Hamed RB, Gomez-Castellanos JR, Henry L, Ducho C, McDonough MA, Schofield C. J. Nat. Prod. Rep. 2013; 30: 21
• 24 Yu M, Gao Y, Zhang L, Zhang Y, Zhang Y, Yi H, Huang Z, Lei A. Green Chem. 2022; 24: 1445
• 25 Zou Z, Cai G, Chen W, Zou C, Li Y, Wu H, Chen L, Hu J, Li Y, Huang Y. J. Org. Chem. 2021; 86: 15777
• 26 Li X.-H, Gong J.-F, Song M.-P. Org. Biomol. Chem. 2021; 19: 5876
• 27 Lamblin M, Couture A, Deniau E, Grandclaudon P. Tetrahedron: Asymmetry 2008; 19: 111
• 28 Karu SK, Malapaka C. Eur. J. Org. Chem. 2023; 26: e202300481
• 29 Amaladass P, Clement JA, Mohanakrishnan AK. Eur. J. Org. Chem. 2008; 3798
• 30 Voltrova S, Srogl J. Synth. Commun. 2015; 45: 2473
• 31 Meek ST, Nesterov EE, Swager TM. Org. Lett. 2008; 10: 2991