Biobased Spiroimides from Itaconic Acid and Formamides: Molecular Targets for a Novel Synthetic Application of Renewable Chemicals

Abstract

Spiroimides exhibit a wide range of biological activities, such as anticonvulsant, antiarrhythmic, and antihyperglycemic activities. Herein, a novel synthetic application of renewable chemicals, itaconic acid and formamides, is described. Proper exploitation of the reactivity of itaconic acid and formamide allows for the development of an efficient synthetic approach for the production of several new biobased spiroimides, spiro[dihydroquinolin-2-one-succinimides] and spiro[indolin-2-one-glutarimides], in excellent overall yields (up to 98%).

Key words

spiroimides - itaconic acid - formamides - renewable building blocks - photochemistry

• References

• 1 Zheng Y, Tice CM, Singh SB. Bioorg. Med. Chem. Lett. 2014; 24: 3673
• 2a Hauck FP, Demick JA, Fan J. J. Med. Chem. 1967; 10: 611
• 2b Tarver ML, Nicholson JM, Scott KR. J. Pharm. Sci. 1985; 74: 785
• 2c Borenstein MR, Doukas PH. J. Pharm. Sci. 1987; 76: 300
• 2d Alexander MS, Stables JP, Ciechanowickz-Rutkowska M, Hursthouse MB, Hibbs DE, Edafiogho IO, Farrar VA, Moore JA, Scott KR. Eur. J. Med. Chem. 1996; 31: 787
• 2e Obniska J, Kamiński K, Chlebek I. Acta Pol. Pharm. 2009; 66: 663
• 2f Obniska J, Byrtus H, Kamiński K, Pawłowski M, Szczesio M, Karolak-Wojciechowska J. Bioorg. Med. Chem. 2010; 18: 6134
• 3 Tenthorey PA, Ronfeld RA, Feldman HS, Sandberg RV, McMaster PD, Smith ER. J. Med. Chem. 1981; 24: 47
• 4a Wrobel J, Dietrich A, Woolson SA, Millen J, McCaleb M, Harrison MC, Hohman TC, Sredy J, Sullivan D. J. Med. Chem. 1992; 35: 4613
• 4b Belletire JL, Sarges R. (Pfizer Inc.) US Patent 4307108, 1981
• 5 Carr AA, Meyer DR. (Richardson-Merrell Inc.) US Patent 3985888, 1976
• 6a Park YH, Barker R, Griffin B, Barratt D, Dupriest M, Brazzell K, York B, Mayer P. Xenobiotica 1992; 22: 543
• 6b Negoro T, Murata M, Fujitani B, Ono Y, Kuromiya A, Komiya M, Suzuki K, Matsumoto J. J. Med. Chem. 1998; 41: 4118
• 6c Constantino L, Rastelli G, Vianello P, Cignarella G, Barlocco D. Med. Res. Rev. 1999; 19: 3
• 7 Malamas MS, Hohman TC, Millen J. J. Med. Chem. 1994; 37: 2043
• 8a Manoharan R, Jeganmohan M. Org. Lett. 2017; 19: 5884
• 8b Zhao H, Shao X, Wang T, Zhai S, Qiu S, Tao C, Wang H, Zhai H. Chem. Commun. 2018; 54: 4927
• 8c Miura W, Hirano K, Miura M. Org. Lett. 2015; 17: 4034
• 8d Ramesh B, Tamizmani M, Jeganmohan M. J. Org. Chem. 2019; 84: 4058
• 9a Brun N, Hesemann P, Esposito D. Chem. Sci. 2017; 8: 4724
• 9b Kühlborn J, Groß J, Opatz T. Nat. Prod. Rep. 2020; 37: 380
• 10a Medway AM, Sperry J. Green Chem. 2014; 16: 2084
• 10b Arnaud SP, Andreou E, Köster LV. G. P, Robert T. ACS Sustainable Chem. Eng. 2020; 8: 1583
• 11a Robert T, Fribels S. Green Chem. 2016; 18: 2922
• 11b Carrasquero FL, Ilarduya AM, Cárdenas M, Carrillo M, Arnal ML, Laredo E, Torres C, Méndez B, Müller A. Polymer 2003; 44: 4969
• 11c Ali MA, Tateyama S, Oka Y, Kaneko D, Okajima MK, Kaneko T. Macromolecules 2013; 46: 3719
• 12a Steiger MG, Blumhoff ML, Mattanovich D, Sauer M. Front. Microbiol. 2013; 4: 23
• 12b Huang X, Chen M, Lu X, Li Y, Li X, Li J.-J. Microb. Cell Fact. 2014; 13: 108
• 13 López-Sepulcre A, Balucani N, Ceccarelli C, Codella C, Dulieu F, Theulé P. ACS Earth Space Chem. 2019; 3: 2122
• 14 Saladino R, Crestini C, Pino S, Costanzo G, Di Mauro E. Phys. Life Rev. 2012; 9: 84
• 15 Adande GR, Woolf NJ, Ziurys LM. Astrobiology 2013; 13: 43
• 16 Morvan DB, Lis DC, Wink JE, Despois D. Astron. Astrophys. 2000; 353: 1103
• 17 Solomon PM. Phys. Today 1973; 26 (03) 32
• 18a Klankermayer J, Wesselbaum S, Beyndoun K, Leitner W. Angew. Chem. Int. Ed. 2016; 55: 7296
• 18b Artz J, Müller TE, Thernet K. Chem. Rev. 2018; 118: 434
• 19a Brann A. J. Am. Chem. Soc. 1918; 40: 793
• 19b Lisnyanskii IM, Kiper NY, Shapira BI. Pharm. Chem. J. 1968; 2: 279
• 19c Schaub T, Paciello R, Pazicky M, Fachinetti G, Preti D. (BASF SE) US Patent 2013/0102807A1, 2013
• 20a Minisci F, Gardini GP. Tetrahedron Lett. 1970; 15
• 20b Correia VG, Abreu JC, Barata CA. E, Andrade LH. Org. Lett. 2017; 19: 1060
• 21a Gowda RR, Chen EY.-X. Org. Chem. Front. 2014; 1: 230
• 21b Lizos DE, Murphy JA. Org. Biomol. Chem. 2003; 1: 117
• 22 Pignatello JJ, Oliveros E, MacKay A. Crit. Rev. Environ. Sci. Technol. 2006; 36: 1
• 23 Sanabria MN, Hornink MM, Correia VG, Andrade LH. Org. Process Res. Dev. 2020;
• 24a Newman SG, Jensen KF. Green Chem. 2013; 15: 1456
• 24b Vaccaro L, Lanari D, Marrocchi A, Strappaveccia G. Green Chem. 2014; 16: 3680
• 24c Mándity IM, Ötvös SO, Fülöp F. Chemistry Open 2015; 4: 212
• 24d Plutschack MB, Pieber B, Gilmore K, Seeberger PH. Chem. Rev. 2017; 117: 11796
• 24e Knowles JP, Elliott LD, Booker-Milburn KI. Beilstein J. Org. Chem. 2012; 8: 2025
• 24f Sambiagio C, Noël T. Trends Chem. 2020; 2: 92
• 25 Nam S, Renganathan V, Tratnyek PG. Chemosphere 2001; 45: 59
• 26 Averesch NJ. H, Winter G, Krömer JO. Microb. Cell Fact. 2016; 15: 1
• 27 Quinlivan EP, Roje S, Basset G, Shachar-Hill Y, Gregory JF. III, Hanson AD. J. Biol. Chem. 2003; 278: 20731
• 28 Wiffen J, Wilson I. (Almac Sciences Limited) WO Patent 2008035086A2, 2008
• 29 Farley AJ. M, Sandford C, Dixon DJ. J. Am. Chem. Soc. 2015; 137: 15992
• 30 Fabry DC, Stodulski M, Hoerner S, Gulder T. Chem. Eur. J. 2012; 18: 10834
• 31 Biswas P, Paul S, Guin J. Angew. Chem. Int. Ed. 2016; 55: 7756
• 32 Efange SM. N, Kamath AP, Khare AB, Kung M.-P, Mach RH, Parsons SM. J. Med. Chem. 1997; 40: 3905