Abstract
An operationally simple and efficient protocol for squaric acid catalyzed synthesis of N-substituted pyrroles via the reaction of 2,5-dimethoxytetrahydrofuran and 2,5-hexandione with aryl amines in green reaction media (water, deep eutectic solvent, and polyethylene glycol) under ultrasound irradiation or thermal conditions in good to excellent yields has been developed.
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Li CJ (2005) Chem Rev 105:3095
Singh S, Lobo H, Shankarling G (2011) Catal Lett 141:178
Mase N, Barbas CF (2010) Org Biomol Chem 8:4043
Wang G, Sun H, Cao X, Chen L (2011) Catal Lett 141:1324
Huang WB, Liu QW, Zheng L-Y, Zhang S-Q (2011) Catal Lett 141:191
Ramesh K, Murthy SN, Nageswar YVD (2012) Synth Commun 42:2471
Gupta RR, Kumar M, Gupta V (1999) Heterocyclic chemistry II: five-membered heterocycles. Springer, Berlin
Sawant P, Maier ME (2010) Tetrahedron 66:9738
Estevez V, Villacampa M, Menendez JC (2012) Chem Soc Rev 39:4402
Bandyopadhyay D, Mukherjee S, Banik BK (2010) Molecules 15:2520
Zhu F-X, Li H-X, Wang W (2011) J Am Chem Soc 133:11632
Abid M, Spaeth A, Török B (2006) Adv Synth Catal 348:2191
Banik BK, Banik I, Renteria M, Dasgupta SK (2005) Tetrahedron Lett 46:2643
Banik BK, Samajdar S, Banik I (2004) J Org Chem 69:213
Chen J, Wu H, Zheng Z, Jin C, Zhang X, Su W (2006) Tetrahedron Lett 47:5383
Minetto G, Raveglia LF, Taddei M (2004) Org Lett 6:389
Polshettiwar V, Baruwati B, Varma RS (2009) Chem Commun 1837
Polshettiwar V, Varma RS (2010) Tetrahedron 66:1091
Song G, Wang B, Wang G, Kang Y, Yang T, Yang L (2005) Synth Commun 35:1051
Bandyopadhyay D, Mukherjee S, Banik BK, Granados JC, Short JD (2012) Eur J Med Chem 50:209
Wang B, Gu Y, Luo C, Yang T, Yang L, Suo J (2004) Tetrahedron Lett 45:3417
Azizi N, Khajeh-Amiri A, Ghafuri H, Bolourtchian M, Saidi MR (2009) Synlett 14:2245
Wilson MA, Filzen G, Welmaker GS (2009) Tetrahedron Lett 50:4807
Yadav JS, Reddy BVS, Eeshwaraiah B, Gupta MK (2004) Tetrahedron Lett 45:5873
Zhang X, Shi J (2011) Tetrahedron 67:898
Rivera S, Bandyopadhyay D, Banik BK (2009) Tetrahedron Lett 50:5445
Azizi N, Saidi MR (2005) Org Lett 7:3649
Azizi N, Torkiyan L, Saidi MR (2006) Org Lett 8:2079
Azizi N, Aryanasab F, Torkiyan L, Ziyaei A, Saidi MR (2006) J Org Chem 71:3634
Storer RI, Aciro C, Jones LH (2011) Chem Soc Rev 40:2330
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The financial support of this work was provided by the Iran National Science Foundation (INSF) and is gratefully appreciated.
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Azizi, N., Davoudpour, A., Eskandari, F. et al. Squaric acid catalyzed simple synthesis of N-substituted pyrroles in green reaction media. Monatsh Chem 144, 405–409 (2013). https://doi.org/10.1007/s00706-012-0841-2
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DOI: https://doi.org/10.1007/s00706-012-0841-2