Abstract
A series of biologically active polysubstituted dihydropyrrol-2-ones are prepared via a one-pot four-component reaction of structurally diverse dialkyl acetylenedicarboxylate, formaldehyde, and amines (aromatic and aliphatic) using a catalytic amount of tartaric acid as a naturally green, mild di-functional Brønsted acid catalyst at ambient temperature. The use of tartaric acid as an inexpensive catalyst makes this procedure eco-friendlier and also one-pot, easily separated from the reaction mixture, good to high yields, short reaction times, simple operational procedures, and highly efficient that are the added advantages of the present methodology.
Similar content being viewed by others
References
Aboonajmi J, Maghsoodlou MT, Hazeri N, Lashkari M, Kangani M (2015) Tartaric acid: a natural, green and highly efficient catalyst for the one-pot synthesis of functionalized piperidines. Res Chem Intermed 41(11):8057–8065
Alp C, Ekinci D, Gultekin MS, Senturk M, Sahin E, Kufrevioglu O (2010) A novel and one-pot synthesis of new 1-tosyl pyrrol-2-one derivatives and analysis of carbonic anhydrase inhibitory potencies. Bioorg Med Chem 18(12):4468–4474
Azab HA, Ahmed IT, Mahmoud MR (1997) Potentiometric determination of the apparent dissociation constants of some dicarboxylic acids in various hydroorganic media. J Chem Eng Data 42(3):593–596
Borthwick AD, Crame AJ, Ertl PF, Exall AM, Haley TM, Hart GJ, Mason AM, Pennell AMK, Singh OMP, Weingarten GG, Woolven J (2002) Design and synthesis of pyrrolidine-5,5-trans-lactams (5-oxohexahydropyrrolo[3,2-b]pyrroles) as novel mechanism-based inhibitors of human cytomegalovirus protease. 2. Potency and chirality. J Med Chem 45(1):1–18
Chen Y, Zeng DX, Xie N, Dang YZ (2005) Study on photochromism of diarylethenes with a 2, 5-dihydropyrrole bridging unit: a convenient preparation of 3, 4-diarylpyrroles from 3,4-diaryl-2,5-dihydropyrroles. J Org Chem 70(13):5001–5005
Clark AC, Prenzler PD, Scollary GR (2007) Impact of the condition of storage of tartaric acid solutions on the production and stability of glyoxylic acid. Food Chem 102(3):905–916
Esmaeilpour M, Sardarian AZ (2013) 4-Dodecylbenzenesulfonic acid (DBSA): an efficient, eco-friendly and chemoselective catalyst for the synthesis of 1, 1-diacetates under solvent-free conditions at room temperature. Iran J Sci Technol 37(3):277–284
Gangwar N, Kumar Kasana V (2011) Tartaric acid-catalyzed synthesis of α-aminophosphonates under solvent-free conditions. Syn Commun 41(18):2800–2804
Hasaninejad A, Yousefy T, Firoozi S (2015) Aluminium dodecyl sulfate trihydrate [Al(DS)3].3H2O: an efficient Lewis acid-surfactant-combined catalyst for synthesis of 1,8-dioxo-octahydroxanthens and 1,8-dioxo-decahydroacridines. Iran J Sci Technol 39(2):129–140
Hashemi H, Sardarian AR (2013) 4-Dodecylbenzenesulfonic acid (DBSA) as an efficient and recyclable catalyst for synthesis of 14-aryl- and 14-alkyl-14-H-dibenzo [a, j]xanthenes under solvent-free conditions. Iran J Sci Technol 37(1):75–82
Khan AT, Ghosh A, Musawwer Khan M (2012) One-pot four-component domino reaction for the synthesis of substituted dihydro-2-oxypyrrole catalyzed by molecular iodine. Tetrahedron Lett 53(21):2622–2626
Lampe YL, Chou RG, Hanna RG, DiMeo SV, Erhardt PW, Hagedorn AA, Ingebretsen WR, Cantor E (1993) (Imidazolylphenyl) pyrrol-2-one inhibitors of cardiac cAMP phosphodiesterase. J Med Chem 36(8):1041–1047
Lv L, Zheng S, Cai X, Chen Z, Zhu Q, Liu S (2013) Development of four-component synthesis of tetra- and pentasubstituted polyfunctional dihydropyrroles: free permutation and combination of aromatic and aliphatic amines. J ACS Comb Sci 15(4):183–192
Marchitan N, Cojocaru C, Mereuta A, Duca G, Cretescu I, Gonta M (2010) Modeling and optimization of tartaric acid reactive extraction from aqueous solutions: a comparison between response surface methodology and artificial neural network. Sep Purif Technol 75(3):273–285
Mohamadpour F, Maghsoodlou MT, Heydari R, Lashkari M (2016a) Saccharin: a green, economical and efficient catalyst for the one-pot, multi-component synthesis of 3,4-dihydropyrimidin-2-(1H)-one derivatives and 1H-pyrazolo [1,2-b] phthalazine-5,10-dione derivatives and substituted dihydro-2-oxypyrrole. Iran J Chem Soc. doi:10.1007/s13738-016-0871-5
Mohamadpour F, Maghsoodlou MT, Heydari R, Lashkari M (2016b) Oxalic acid dihydrate catalyzed synthesis of 3,4-dihydropyrimidin-2-(1H)-one derivatives under thermal and solvent-free conditions. Iran J Catal 6(2):127–131
Rezayati S, Sajjadifar S, Hajinasiri R (2015) Chemoselective preparation of acylals using 1-methyl-3-(2-(sulfooxy)ethyl)-1H-imidazol-3-ium chloride as an efficient and reusable catalyst. Iran J Sci Technol 39(2):179–185
Saberi A (2015) Efficient synthesis of benzimidazoles using zeolite, alumina and silica gel under microwave irradiation. Iran J Sci Technol 39(1):7–10
Sajadikhah SS, Hazeri N, Maghsoodlou MT (2013a) A one-pot multi-component synthesis of N-aryl-3-aminodihydropyrrl-2-one-4-carboxylate catalyzed by oxalic acid dehydrate. J Chem Res 37(1):40–42
Sajadikhah SS, Hazeri N, Maghsoodlou MT, Habibi-Khorassani SM, Beigbabaei A, Willis AC (2013b) Al(H2 PO4)3 as an efficient and reusable catalyst for the multi-component synthesis of highly functionalized piperidines and dihydro-2-oxypyrroles. J Iran Chem Soc 10(5):863–871
Sajadikhah SS, Maghsoodlou MT, Hazeri N (2014) A simple and efficient approach to one-pot synthesis of mono- and bis-N-aryl-3-aminodihidropyrrol-2-one-4-carboxylate catalyzed by InCl3. Chin Chem Lett 25(1):58–60
Sajadikhah SS, Maghsoodlou MT, Hazeri N, Mohamadian-Souri S (2015) ZrCl4 as an efficient catalyst for one-pot four-component synthesis of polysubstituted dihydropyrrol-2-ones. Res Chem Intermed. doi:10.1007/s11164-015-2178-z
Sharghi H, Khoshnood A, Khalifeh R (2012) Three-component synthesis of propargylamine derivatives via 1,4-dihydroxyanthraquinone-copper(II) complexes as an efficient catalyst under solvent-free conditions. Iran J Sci Technol 36(1):25–35
Shiraki R, Sumino A, Tadano K, Ogawa S (1995) Total synthesis of PI-091. Tetrahedron Lett 36(31):5551–5554
Singh SB, Goetz MA, Jones ET, Billes GF, Giacobbe RA, Herranz L, Stevens-Miles S, Williams DL (1995) A novel antagonist of endothelin receptor. J Org Chem 60(21):7040–7042
Snider BB, Neubert BJ (2004) A novel biomimetic route to the 3-acyl-5-hydroxy-3-pyrrolin-2-one and 3-acyl-3, 4-epoxy-5-hydroxypyrrolidin-2-one systems. J Org Chem 69(25):8952–8955
Zhang K, Wang M, Wang D, Gao C (2009) The energy-saving production of tartaric acid using ion exchange resin-filling bipolar membrane electrodialysis. J Membr Sci 341(1–2):246–251
Zhu Q, Jiang H, Li J, Liu S, Xia C, Zhang M (2009) Concise and versatile multicomponent synthesis of multisubstituted polyfunctional dihydropyrroles. J Comb Chem 11(4):685–696
Acknowledgments
We gratefully acknowledge financial support from the research council of the university of Sistan and Baluchestan.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Mohamadpour, F., Maghsoodlou, M.T., Heydari, R. et al. Tartaric Acid: A Naturally Green and Efficient Di-Functional Brønsted Acid Catalyst for the One-Pot Four-Component Synthesis of Polysubstituted Dihydropyrrol-2-Ones at Ambient Temperature. Iran J Sci Technol Trans Sci 41, 843–849 (2017). https://doi.org/10.1007/s40995-016-0049-0
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s40995-016-0049-0