Recent Developments in Isoindole Chemistry

Abstract

Isoindoles are highly reactive aromatic heterocycles that have a variety of important applications in areas such as medicine, analytical detection, and solar energy. Due to their highly reactive nature, isoindoles can be used to access their derivatives, which possess a diverse array of biological activities. However, their reactivity also makes isoindoles unstable and thus, difficult to prepare. Consequently, there has been a need for the development of novel methods that address some of the synthetic challenges and limitations, as well as reactions that utilize isoindoles to access potentially useful compounds. This review will give an overview of the novel reactions reported within the past decade (2012 to 2022) that involve 2H- and 1H-isoindoles and fused isoindoles as reactants, key intermediates, or products. This review is divided into two parts, with the first part focusing on the synthesis of isoindoles and the second part focusing on reactions of isoindoles. The scopes and limitations of the methods described therein will be discussed and the significance of their contributions to the literature will be highlighted. Similar reactions will also be compared.

1 Introduction

2 Synthesis of Isoindoles

2.1 Synthesis of 2H-Isoindoles

2.2 Synthesis of 1H-Isoindoles

3 Reactions of Isoindoles

3.1 Reactions of 2H-Isoindoles

3.2 Reactions of 1H-Isoindoles

4 Conclusions

Key words

isoindole - 2H-isoindole - 1H-isoindole - isoindoline - isoindolinone - phthalimide

Publikationsverlauf

Eingereicht: 16. September 2022

Angenommen nach Revision: 17. Oktober 2022

Artikel online veröffentlicht:
16. November 2022

• References

• 1 White JD, Mann ME. Adv. Heterocycl. Chem. 1969; 10: 113
• 2 Katritzky AR, Ramsden CA, Joule JA, Zhdankin VV. Handbook of Heterocyclic Chemistry 2010
• 3 Bonnett R, North SA. Adv. Heterocycl. Chem. 1981; 29: 341
• 4 Joule JA, Mills K. Heterocyclic Chemistry, 5th Ed. Wiley-VCH; Weinheim: 2010. chapter 22
• 5 Heugebaert TS. A, Roman BI, Stevens CV. Chem. Soc. Rev. 2012; 41: 5626
• 6 Veber DF, Lwowski W. J. Am. Chem. Soc. 1963; 85: 646
• 7 Weintraub RA, He W, Wang X. Tetrahedron Lett. 2020; 61: 152128
• 8 Farghaly TA, Al-Hussain SA, Muhammad ZA, Abdallah MA, Zaki ME. A. Curr. Org. Chem. 2020; 24: 1669
• 9 Voitenko ZV, Sypchenko VV, Levkov IV, Potikha LM, Kovtunenko VA, Shishkin OV, Shishkina SV. J. Chem. Res. 2011; 35: 615
• 10 Ohmura T, Kijima A, Suginome M. Org. Lett. 2011; 13: 1238
• 11 Voitenko ZV, Pokholenko OA, Ilkun OT, Mazières MR, Wolf JG. C. R. Chim. 2006; 9: 1482
• 12 Samoylenko VP, Voitenko ZV, Donnadieu B, Bonnet J.-J. Tetrahedron 2002; 58: 6103
• 13 Kovtunenko VA, Voitenko ZV, Kucherenko TT, Turov AV, Tyltin AK, Babichev FS. Chem. Heterocycl. Compd. 1990; 26: 161
• 14 Kovtunenko VA, Dobrenko TT, Voitenko ZV, Tyltin AK, Babichev FS. Chem. Heterocycl. Compd. 1984; 20: 978
• 15 Bonnett R, North SA, Newton RF, Scopes DI. C. Tetrahedron 1983; 39: 1401
• 16 Ciganek E. J. Org. Chem. 1980; 45: 1497
• 17 Diana P, Martorana A, Barraja P, Montalbano A, Carbone A, Cirrincione G. Tetrahedron 2011; 67: 2072
• 18 Hordiyenko OV, Rudenko IV, Biitseva AV, Turov AV, Arrault A, Brosse N, Fabre O, Jamart-Grégoire B, Zubatyuk RI, Shishkin OV. Tetrahedron 2009; 65: 6218
• 19 Babichev FS, Kovtunenko VA, Tyltin AK. Russ. Chem. Rev. 1981; 50: 1087
• 20 Winn M, Zaugg HE. J. Org. Chem. 1969; 34: 249
• 21 Kreher RP, Hennige H, Jelitto F, Preut J. Z. Naturforsch., B 1989; 44: 1132
• 22 Kochi JK, Singleton EA. Tetrahedron 1968; 24: 4649
• 23 Fletcher H. Tetrahedron 1966; 22: 2481
• 24 Kreher R, Seubert J. Angew. Chem. Int. Ed. Engl. 1966; 5: 967
• 25 Bender CO, Bonnett R. Chem. Commun. 1966; 198
• 26 Emmett JC, Veber DF, Lwowski W. Chem. Commun. 1965; 272
• 27 Kreher R, Seubert J. Angew. Chem. 1964; 76: 682 ; Angew. Chem. Int. Ed. Engl. 1964, 3, 639
• 28 Speck K, Magauer T. Beilstein J. Org. Chem. 2013; 9: 2048
• 29 Manoj KM, Satheesh KN, Narasimha ST, Ravinder M, Thurpurani MK, Sirassu N. J. Mol. Struct. 2022; 1250: 131722
• 30 Sović I, Jambon S, Kraljević Pavelić S, Markova-Car E, Ilić N, Depauw S, David-Cordonnier M.-H, Karminski-Zamola G. Bioorg. Med. Chem. 2018; 26: 1950
• 31 Kumar S, Waldo JP, Jaipuri FA, Marcinowicz A, Van Allen C, Adams J, Kesharwani T, Zhang X, Metz R, Oh AJ, Harris SF, Mautino MR. J. Med. Chem. 2019; 62: 6705
• 32 Capochiani de Iudicibus R, Tomek P, Palmer BD, Tijono SM, Flanagan JU, Ching L.-M. Bioorg. Med. Chem. 2021; 39: 116160
• 33 Nayak-Kapoor A, Hao Z, Sadek R, Dobbins R, Marshall L, Vahanian NN, Jay Ramsey W, Kennedy E, Mautino MR, Link CJ, Lin RS, Royer-Joo S, Liang X, Salphati L, Morrissey KM, Mahrus S, McCall B, Pirzkall A, Munn DH, Janik JE, Khleif SN. J. Immunother. Cancer 2018; 6: 61
• 34 Narsimha S, Battula K, Vasudeva Reddy N. Synth. Commun. 2017; 47: 928
• 35 Guzior N, Bajda M, Skrok M, Kurpiewska K, Lewinski K, Brus B, Pislar A, Kos J, Gobec S, Malawska B. Eur. J. Med. Chem. 2015; 92: 738
• 36 Yu L, Shi J, Cheng X, Wang K, Liu S, Liu W, Sang Z. Lett. Drug Des. Discovery 2020; 17: 1155
• 37 Xu F, Chen H, Xu J, Liang X, He X, Shao B, Sun X, Li B, Deng X, Yuan M. Bioorg. Med. Chem. 2015; 23: 7735
• 38 Gao JC, Wu AG, Contento MN, Maher JM, Cline A. Clin., Cosmet. Invest. Dermatol. 2022; 15: 395
• 39 Lee I.-K, Kim S.-E, Yeom J.-H, Ki D.-W, Lee M.-S, Song J.-G, Kim Y.-S, Seok S.-J, Yun B.-S. J. Antibiot. 2012; 65: 95
• 40 Wang J.-N, Zhang H.-J, Li J.-Q, Ding W.-J, Ma Z.-J. J. Nat. Prod. 2018; 81: 949
• 41 Wang X.-L, Xu K.-P, Long H.-P, Zou H, Cao X.-Z, Zhang K, Hu J.-Z, He S.-J, Zhu G.-Z, He X.-A, Xu P.-S, Tan G.-S. Fitoterapia 2016; 111: 58
• 42 El-Said WA, Qaisi RM, Placide V, Choi J. Spectrochim. Acta, Part A 2022; 267: 120517
• 43 Abdel-Lateef MA, Almahri A. Spectrochim. Acta, Part A 2021; 258: 119806
• 44 Duhamel P, Ounissi M, Le Saux T, Bienayme H, Chiron C, Jullien V. J. Chromatogr. B 2017; 1070: 31
• 45 Beketov VI, Voronina RD, Zorov NB. Moscow Univ. Chem. Bull. 2012; 67: 149
• 46 Notou M, Zotou A, Tzanavaras PD, Themelis DG. J. Chromatogr. A 2014; 1356: 272
• 47 Yu C, Wu Q, Wang J, Wei Y, Hao E, Jiao L. J. Org. Chem. 2016; 81: 3761
• 48 Wang J, Wu Q, Xu Y, Yu C, Wei Y, Mu X, Hao E, Jiao L. RSC Adv. 2016; 6: 52180
• 49 Rizvi W, Berisha N, Farley C, Bhupathiraju NV. S. D. K, Andreou C, Khwaja E, Fuentes GV, Kircher MF, Gao R, Drain CM. Chem. Eur. J. 2019; 25: 14517
• 50 Revuelta-Maza MA, Hally C, Nonell S, de la Torre G, Torres T. ChemPlusChem 2019; 84: 673
• 51 Revuelta-Maza MA, Nonell S, de la Torre G, Torres T. Org. Biomol. Chem. 2019; 17: 7448
• 52 Fazio E, Jaramillo-García J, Medel M, Urbani M, Grätzel M, Nazeerudin MK, de la Torre G, Torres T. ChemistryOpen 2017; 6: 121
• 53 Fazio E, Jaramillo-García J, de la Torre G, Torres T. Org. Lett. 2014; 16: 4706
• 54 Takao Y, Masuoka T, Yamamoto K, Mizutani T, Matsumoto F, Moriwaki K, Hida K, Iwai T, Ito T, Mizuno T, Ohno T. Tetrahedron Lett. 2014; 55: 4564
• 55 Sypchenko VV, Potikha LM, Kovtunenko VA, Baumer VN, Shishkin OV. Chem. Heterocycl. Compd. 2012; 48: 1033
• 56 Zhang Y, Lee CL, Liu H, Li X. Org. Lett. 2012; 14: 5146
• 57 Hargitai C, Koványi-Lax G, Nagy T, Ábrányi-Balogh P, Dancsó A, Halász J, Tóth G, Simig G, Volk B. Monatsh. Chem. 2019; 150: 1121
• 58 Asako S, Kobashi T, Takai K. J. Am. Chem. Soc. 2018; 140: 15425
• 59 Zhen L, Dai L, Yu S.-Q, Lin C, Sun H, Xu Q.-L. Eur. J. Org. Chem. 2017; 2017: 560
• 60 Lin C, Zhen L, Cheng Y, Du H.-J, Zhao H, Wen X, Kong L.-Y, Xu Q.-L, Sun H. Org. Lett. 2015; 17: 2684
• 61 Ding G, Wu X, Jiang L, Zhang Z, Xie X. Org. Lett. 2017; 19: 6048
• 62 Starosotnikov A, Bastrakov M, Kachala V, Belyakov P, Fedyanin I, Shevelev S. Synlett 2012; 23: 2400
• 63 Fang Y, Larock RC, Shi F. Asian J. Org. Chem. 2014; 3: 55
• 64 Lopchuk JM, Gribble GW. Tetrahedron Lett. 2014; 55: 2809
• 65 Ito S, Akaki M, Shinozaki Y, Iwabe Y, Furuya M, Tobata M, Roppongi M, Sato T, Itoh N, Oba T. Tetrahedron Lett. 2017; 58: 1338
• 66 Qi B, Li L, Wang Q, Zhang W, Fang L, Zhu J. Org. Lett. 2019; 21: 6860
• 67 Li Y, Zhou J, Fang F, Xu B, Liu H, Zhou Y. J. Org. Chem. 2018; 83: 11736
• 68 Zhu J, Li R, Su Y, Gu P. J. Org. Chem. 2019; 84: 5813
• 69 Wu R, Gao S, Chen X, Yang G, Pan L, Hu G, Jia P, Zhong W, Yu C. Eur. J. Org. Chem. 2014; 2014: 3379
• 70 Liu S, Hu X, Li X, Cheng J. Synlett 2013; 24: 847
• 71 Zhao B, Yu M, Liu H, Chen Y, Yuan Y, Xie X. Adv. Synth. Catal. 2014; 356: 3295
• 72 Asako S, Kobayashi T, Ishihara S, Takai K. Asian J. Org. Chem. 2021; 10: 753
• 73 Grosheva D, Cramer N. Angew. Chem. Int. Ed. 2018; 57: 13644
• 74 Wang J, Li L, Chai M, Ding S, Li J, Shang Y, Zhao H, Li D, Zhu Q. ACS Catal. 2021; 11: 12367
• 75 Tang S, Yang S.-W, Sun H, Zhou Y, Li J, Zhu Q. Org. Lett. 2018; 20: 1832
• 76 Wang Q, Li Y, Qi Z, Xie F, Lan Y, Li X. ACS Catal. 2016; 6: 1971
• 77 Yi Y, Lee H, Jun C.-H. Chem. Commun. 2016; 52: 10171
• 78 Lv N, Chen Z, Liu Y, Liu Z, Zhang Y. Org. Lett. 2017; 19: 2588
• 79 Manikandan R, Tamizmani M, Jeganmohan M. Org. Lett. 2017; 19: 6678
• 80 Ye P, Shao Y, Xie L, Shen K, Cheng T, Chen J. Chem. Asian J. 2018; 13: 3681
• 81 Yao T, Liang X, Guo Z, Yang D. Tetrahedron 2019; 75: 3088
• 82 Kuroda M, Kobayashi K. Helv. Chim. Acta 2015; 98: 279
• 83 Kobayashi K, Matsumoto K, Shirai Y, Ishikawa H, Inouchi H, Tanmatsu M. Helv. Chim. Acta 2014; 97: 915
• 84 Yegorova TV, Shishkina SV, Zubatyuk RI, Tsapko MD, Shishkin OV, Voitenko ZV. Tetrahedron 2019; 75: 2018
• 85 Baglai I, Maraval V, Voitenko ZV, Duhayon C, Volovenko YM, Chauvin R. Turk. J. Chem. 2014; 38: 121
• 86 Ohmura T, Kijima A, Komori Y, Suginome M. Org. Lett. 2013; 15: 3510
• 87 Yao T, Xia T, Yan W, Xu H, Zhang F, Xiao Y, Zhang J, Liu L. Org. Lett. 2020; 22: 4511
• 88 Baglai I, Maraval V, Voitenko ZV, Duhayon C, Volovenko YM, Chauvin R. Tetrahedron 2012; 68: 6908
• 89 Levkov IV, Cassel S, Voitenko ZV, Palamarchuk GV, Shishkin OV, Shishkina SV, Lattes A, Rico-Lattes I. Heterocycles 2012; 85: 1671