One-Pot Synthesis of Highly Functionalized Benzimidazolylisophthalates and (2E)-2-Ethylidene-(1H)-pyridinecarboxylates by Ultrasound-Promoted Multicomponent Reactions

Abstract

Reaction of 3-formylchromones, 2-aminobenzimidazole, and acetonedicarboxylates under ultrasound irradiation afforded alkyl 2-(1H-benzimidazol-2-ylamino)-5-(2-hydroxyaroyl)isophthalates as the only reaction product in almost quantitative yields. However, when 2-aminobenzimidazole was replaced by aromatic amines novel alkyl 1-aryl-2-[(E)-2-alkoxy-2-oxoethylidene]-5-(2-hydroxyaroyl)-(1H)-pyridine-3-carboxylates were isolated in good yields. A plausible mechanistic scheme for the formation of the isolated isophthalates and pyridine carboxylates is proposed, and full assignment of all their ¹H and ¹³C NMR chemical shifts has been unambiguously achieved. In addition, the lipid peroxidation inhibition of the novel isophthalate derivatives was evaluated, and it was found that one such derivative presents an interesting antilipid peroxidation activity.

Key words

acetonedicarboxylates - 2-aminobenzimidazole - aroylpyridines - benzophenones - 3-formylchromones

• References

• 1 Luche J.-L. Synthetic Organic Sonochemistry . Plenum Press; New York: 1998
• 2 Advances in Sonochemistry . Vol. 1. Mason TJ. JAI Press; London: 1990
• 3 Cintas P, Luche J.-L. Green Chem. 1999; 1: 115
• 4 Cella R, Stefani HA. Tetrahedron 2009; 65: 2619
• 5 Zhu J, Bienaymé H. Multicomponent Reactions . Wiley-VCH; Weinheim: 2005
• 6 Touré BB, Hall DG. Chem. Rev. 2009; 109: 4439
• 7 Sunderhaus JD, Martin SF. Chem. Eur. J. 2009; 15: 1300
• 8 Isambert N, Lavilla R. Chem. Eur. J. 2008; 14: 8444
• 9a Dömling A. Chem. Rev. 2006; 106: 17
• 9b Bugaut X, Bonne D, Coquerel Y, Rodriguez J, Constantieux T. Curr. Org. Chem. 2013; 17: 1920
• 10 Terzidis MA, Stephanidou-Stephanatou J, Tsoleridis CA. J. Org. Chem. 2010; 75: 1948
• 11 Zarganes-Tzitzikas T, Terzidis MA, Stephanidou-Stephanatou J, Tsoleridis CA, Kostakis GE. J. Org. Chem. 2011; 76: 9008
• 12 Terzidis MA, Zarganes-Tzitzikas T, Tsimenidis C, Stephanidou-Stephanatou J, Tsoleridis CA, Kostakis GE. J. Org. Chem. 2012; 77: 9018
• 13 Khadem S, Marles RJ. Molecules 2012; 17: 191
• 14 Masters K.-S, Bräse S. Chem. Rev. 2012; 112: 3717
• 15 Harborne JB, Williams CA. Nat. Prod. Rep. 2001; 18: 310
• 16 Brigelius-Flohé R. Biol. Med. 2009; 46: 543
• 17 Atkinson J, Epand RF, Epand RM. Free Rad. Biol. Med. 2008; 44: 739
• 18 Lozinskii OA, Shokol TV, Khilya VP. Chem. Heterocycl. Comp. 2011; 47: 1055
• 19 Nicolaou KC, Pfefferkorn JA, Roecker AJ, Cao G.-Q, Barluenga S, Mitchell HJ. J. Am. Chem. Soc. 2000; 122: 9939
• 20 Horton DA, Bourne GT, Smythe ML. Chem. Rev. 2003; 103: 893
• 21 Alamgir M, Black DSt. C, Kumar N. Top. Heterocycl. Chem. 2007; 9: 87 ; and references therein
• 22 Zhan P, Li D, Li J, Chen X, Liu X. Mini-Rev. Org. Chem. 2012; 9: 397
• 23 Bansal Y, Silakari O. Bioorg. Med. Chem. 2012; 20: 6208
• 24 Barot KP, Nikolova S, Ivanov I, Ghate MD. Mini-Rev. Med. Chem. 2013; 13: 1421
• 25 Frei R, Breitbach AS, Blackwell HE. Angew. Chem. Int. Ed. 2012; 51: 5226
• 26a The Merck Index . 13th ed.; O’Neil MJ, Smith A, Heckelman PE, Budavari S. Merck & Co; Whitehouse Station (NJ, USA): 2001: 393
• 26b The Merck Index . 13th ed.; O’Neil MJ, Smith A, Heckelman PE, Budavari S. Merck & Co; Whitehouse Station (NJ, USA): 2001: 831
• 26c The Merck Index . 13th ed.; O’Neil MJ, Smith A, Heckelman PE, Budavari S. Merck & Co; Whitehouse Station (NJ, USA): 2001: 894
• 26d The Merck Index . 13th ed.; O’Neil MJ, Smith A, Heckelman PE, Budavari S. Merck & Co; Whitehouse Station (NJ, USA): 2001: 1164
• 27 Zhao Z. Chinese Patent CN 1457786, 2003 ; Chem. Abstr. 2005; 142, 379358
• 28 Lee LF, Glenn KC, Connolly DT, Corley DG, Flynn DL, Hamme A, Hegde SG, Melton MA, Schilling RJ, Sikorski JA, Wall NN, Zablocki JA. PCT Int. Appl WO 9941237, 1999 ; Chem. Abstr. 1999, 131, 157711
• 29 Bharate SB, Mahajan TR, Gole YR, Nambiar M, Matan TT, Kulkarni-Almeida A, Balachandran S, Junjappa H, Balakrishnan A, Vishwakarma RA. Bioorg. Med. Chem. 2008; 16: 7167
• 30 Galal SA, Abd El-All AS, Abdallah MM, El-Diwani HI. Bioorg. Med. Chem. Lett. 2009; 19: 2420
• 31 Terzidis MA, Tsoleridis CA, Stephanidou-Stephanatou J, Terzis A, Raptopoulou CP, Psycharis V. Tetrahedron 2008; 64: 11611
• 32 Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JA. Jr, Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X, Knox JE, Hratchian HP, Cross JB, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PM. W, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA. Gaussian 03, Revision B. 02 . Gaussian, Inc; Pittsburgh: 2003
• 33 Hadjipavlou-Litina D, Magoulas GE, Bariamis SE, Drainas D, Avgoustakis K, Papaioannou D. Bioorg. Med. Chem. 2010; 18: 8204