Efficient and Green Microwave-Assisted Multicomponent Biginelli Reaction for the Synthesis of Dihydropyrimidinones Catalyzed by Heteropolyanion-Based Ionic Liquids Under Solvent-Free Conditions

REFERENCES

• (a) Dömling, A. Chem. Rev. 2006, 106, 17–89; (b) González-López, M.; Shaw, J. T. Chem. Rev. 2009, 109, 164–189; (c) Yu, J.; Shi, F.; Gong, L. Acc. Chem. Res. 2011, 44, 1156–1171; (d) Nair, V.; Menon, R. S.; Biju, A. T.; Abhilash, K. G. Chem. Soc. Rev. 2012, 41, 1050–1059; (e) Kolla, S. R.; Lee, Y. R. Tetrahedron 2012, 68, 226–237; (f) Pellissier, H. Chem. Rev. 2013, 113, 442–524.
   PubMed Web of Science ®Google Scholar
• (a) Chen, W.; Wu, Z.; Pei, Q.; Cun, L.; Zhang, X.; Yuan, W. Org. Lett. 2010, 12, 3132–3135; (b) Cerulli, V.; Banfi, L.; Basso, A.; Rocca, V.; Riva, R. Org. Biomol. Chem. 2012, 10, 1255–1274; (c) Estévez, V.; Villacampa, M.; Menéndez, J. C. Chem. Soc. Rev. 2010, 39, 4402–4421; (d) Climent, M. J.; Corma, A.; Iborra, S. Chem. Rev. 2011, 111, 1072–1133; (e) Isambert, N.; Duque, M. M. S.; Plaquevent, J.; Génisson, Y.; Rodriguez, J.; Constantieux, T. Chem. Soc. Rev. 2011, 40, 1347–1357; (f) Volla, C. M. R.; Atodiresei, I.; Rueping, M. Chem. Rev. 2014, 114, 2390–2431.
   PubMed Web of Science ®Google Scholar
• (a) Kappe, C. O. Acc. Chem. Res. 2000, 33, 879–888 (b) Panda, S. S.; Khanna, P.; Khanna, L. Curr. Org. Chem., 2012, 16, 507–520; (c) Suresh; Sandhu, J. S. Arkivoc 2012, 1, 66–133.
   PubMed Web of Science ®Google Scholar
• (a) Kappe, C. O. Eur. J. Med. Chem. 2000, 35, 1043–1052; (b) Kidwai, M.; Saxena, S.; Khan, M. K. R.; Thukral, S. S. Eur. J. Med. Chem. 2005, 40, 816–818; (c) Deshmukh, M. B.; Salunkhe, S. M.; Patil, D. R.; Anbhule, P. V. Eur. J. Med. Chem. 2009, 44, 2651–2654; (d) Singh, K.; Arora, D.; Poremsk, E.; Lowery, J.; Moreland, R. S. Eur. J. Med. Chem. 2009, 44, 1997–2001; (e) Kumar, B. R. P.; Sankar, G.; Baig, R. B. N.; Chandrashekaran, S. Eur. J. Med. Chem. 2009, 44, 4192–4198; (f) da Silva, D. L.; Reis, F. S.; Muniz, D. R.; Ruiz, A. L. T. G.; de Carvalho, J. E.; Sabino, A. A.; Modolo, L. V.; de Fatima, A. Bioorg. Med. Chem. 2012, 20, 2645–2650.
   PubMed Web of Science ®Google Scholar
• (a) Chanetskyy, B.; Dallinger, D.; Kappe, C. O. J. Comb. Chem. 2004, 6, 884–892; (b) Yamamoto, K.; Chen, Y. G.; Buono, F. G. Org. Lett. 2005, 7, 4673–4676; (c) Kim, S. S.; Choi, B. S.; Lee, J. H.; Lee, K. K.; Lee, T. H.; Kim, Y. H.; Hyunik, S. Synlett 2009, 599–602.
   PubMed Web of Science ®Google Scholar
• (a) Biginelli, P. Gazz. Chim. Ital. 1893, 23, 360–413 (b) Atwal, K. S.; Rovnyak, G. C.; O’Reilly, B. C.; Schwartz, J. J. Org. Chem. 1989, 54, 5898–5907; (c) Barluenga, J.; Tomás, M.; Ballesteros, A.; López, L. A. Tetrahedron Lett. 1989, 30, 4573–4576.
   Google Scholar
• (a) Yu, Y.; Liu, C.; Luo, G. Bioorg. Med. Chem. Lett. 2007, 17, 3508–3510; (b) Polshettiwar, V.; Varma, R. S. Tetrahedron Lett. 2007, 48, 7343–7346; (c) Shobha, D.; Chari, M. A.; Ahn, K. H. Chin. Chem. Lett. 2009, 20, 1059–1061 (d) Wang, Y.; Yu, J.; Yang, H.; Miao, Z.; M.; Chen, R. Lett. Org. Chem. 2011, 8, 264–267; (e) Gore, S.; Baskaran, S.; Koenig, B. Green Chem. 2011, 13, 1009–1013; (f) Ren, Y.; Cai, C.; Yang, R. RSC Adv. 2013, 3, 7182–7204.
   PubMed Web of Science ®Google Scholar
• (a) Shen, Z.; Xu, X.; Ji, S. J. Org. Chem. 2010, 75, 1162–1167; (b) Tamaddon, F.; Razmi, Z.; Jafari, A. A. Tetrahedron Lett. 2010, 51, 1187–1189.
   PubMed Web of Science ®Google Scholar
• (a) Lannou, M.; Hélion, F.; Namy, J. Synlett 2008, 105–107; (b) Prodius, D.; Macaev, F.; Mereacre, V.; Shova, S.; Lutsenco, Y.; Styngach, E.; Ruiz, P.; Muraviev, D.; Lipkowski, J.; Simonov, Y. A.; Turta, C. Inorg. Chem. Commun. 2009, 12, 642–645; (c) Chitra, S.; Pandiarajan, K. Tetrahedron Lett. 2009, 50, 2222–2224; (d) Litvić, M.; Večenaj, I.; Ladišić, Z. M.; Lovrić, M.; Vinković, V.; Litvić, M. F. Tetrahedron 2010, 66, 3463–3471; (e) Sadek, K. U.; Al-Qalaf, F.; Abdelkhalik, M. M.; Elnagdi, M. H. J. Heterocycl. Chem. 2010, 47, 284–286; (f) Narsaiah, A. V.; Reddy, A. R.; Yadav, J. S. Synth. Commun. 2011, 41, 2794–2799 (g) Lei, M.; Ma, L.; Hu, L. Synth. Commun. 2011, 41, 3071–3077; (h) Pasunooti, K. K.; Chai, H.; Jensen, C. N.; Gorityala, B. K.; Wang, S.; Liu, X. Tetrahedron Lett. 2011, 52, 80–84; (i) Starcevich, J. T.; Laughlin, T. J.; Mohan, R. S. Tetrahedron Lett. 2013, 54, 983–985.
   Google Scholar
• (a) Mandhane, P. G.; Joshi, R. S.; Nagargoje, D. R.; Gill, C. H. Tetrahedron Lett. 2010, 51, 3138–3140; (b) Rao, G. B. D.; Acharya, B. N.; Verma, S. K.; Kaushik, M. P. Tetrahedron Lett. 2011, 52, 809–812; (c) Silva, D. L.; Fernandes, S. A.; Sabino, A. A.; Fátima, Â. Tetrahedron Lett. 2011, 52, 6328–6330; (d) Verma, S.; Jain, S. L. Tetrahedron Lett. 2012, 53, 2595–2600; (e) Xu, F.; Huang, D.; Lin, X.; Wang, Y. Org. Biomol. Chem. 2012, 10, 4467–4470; (f) Nagarapu, L.; Gaikwad, H. K.; Palem, J. D.; Venkatesh, R.; Bantu, R.; Sridhar, B. Synth. Commun. 2013, 43, 93–104.
   Web of Science ®Google Scholar
• (a) Cheng, Q.; Wang, Q.; Xu, X.; Ruan, M.; Yao, H.; Yang, X. J. Heterocycl. Chem. 2010, 47, 624–628; (b) Shobha, D.; Chari, M. A.; Mano, A.; Selvan, S. T.; Mukkanti, K.; Vinu, A. Tetrahedron 2009, 65, 10608–10611; (c) Verma, S.; Jain, S. L.; Sain, B. Tetrahedron Lett. 2010, 51, 6897–6900; (d) Li, P.; Regati, S.; Butcher, R. J.; Arman, H. D.; Chen, Z.; Xiang, S.; Chen, B.; Zhao, C. Tetrahedron Lett. 2011, 52, 6220–6222; (e) Konkala, K.; Sabbavarapu, N. M.; Katla, R.; Durga, N. Y. V.; Reddy, T. V. K.; Bethala, L.A. P. D.; Rachapudi, B. N. P. Tetrahedron Lett. 2012, 53, 1968–1973; (f) Narahari, S. R.; Reguri, B. R.; Gudaparthi, O.; Mukkanti, K. Tetrahedron Lett. 2012, 53, 1543–1545; (g) Sahu, P. K.; Sahu, P. K.; Agarwal, D. D. RSC Adv. 2013, 3, 9854–9864; (h) Shi, X.; Yang, H.; Tao, M.; Zhang, W. RSC Adv. 2013, 3, 3939–3945.
   Web of Science ®Google Scholar
• (a) Miao, W.; Chan, T. H. Acc. Chem. Res. 2006, 39, 897–908; (b) Chowdhury, S.; Moha, R. S.; Scott, J. L. Tetrahedron 2007, 63, 2363–2389; (c) Greaves, T. L.; Drummond, C. J. Chem. Rev. 2008, 108, 206–237.
   PubMed Web of Science ®Google Scholar
• (a) Plechkova, N. V.; Seddon, K. R. Chem. Soc. Rev. 2008, 37, 123–150; (b) Petkovic, M.; Seddon, K. R.; Rebelo, L. P. N.; Pereira, C. S. Chem. Soc. Rev. 2011, 40, 1383–1403; (c) Isambert, N.; Duque, M. M. S.; Plaquevent, J. C.; Rodriguez, J.; Constantieux, T. Chem. Soc. Rev. 2011, 40, 1347–1357.
   PubMed Web of Science ®Google Scholar
• (a) Peng, J. J.; Deng, Y. Q. Tetrahedron Lett. 2001, 42, 5917–5919; (b) Wasserscheid, P.; Hal, R. V.; Bösmann, A. Green Chem. 2002, 4, 400–404; (c) Shaabani, A.; Rahmati, A. Catal. Lett. 2005, 100, 177–179; (d) Li, M.; Guo, W. S.; Wen, L. R.; Li, Y. F.; Yang, H. Z. J. Mol. Catal. A: Chem. 2006, 258, 133–138; (e) Zheng, R.; Wang, X.; Xu, H.; Du, J. Synth. Commun. 2006, 36, 1503–1513; (f) Fang, D.; Luo, J.; Zhou, X.; Ye, Z.; Liu, Z. J. Mol. Catal. A: Chem. 2007, 274, 208–211; (g) Roy, S. R.; Jadhavar, P. S.; Seth, K.; Sharma, K. K.; Chakraborti, A. K. Synthesis 2011, 2261–2267; (h) Kore, R.; Srivastava, R. J. Mol. Catal. A: Chem. 2011, 345, 117–126; (i) Hajipour, A. R.; Seddighi, M. Synth. Commun. 2012, 42, 227–235; (j) Sharma, N.; Sharma, U. K.; Kumar, R.; Richa; Sinha, A. K. RSC Adv. 2012, 2, 10648–10651; (k) Ramos, L. M.; Tobio, A. Y. P. L.; Santos, M. R.; Oliveira, H. C. B.; Gomes, A. F.; Gozzo, F. C.; Oliveira, A. L.; Neto, B. A. D. J. Org. Chem. 2012, 77, 10184–10193; (l) Zhu, A.; Li, Q.; Li, L.; Wang, J. Catal. Lett. 2013, 143, 463–468 (m) Ramos, L. M.; Guido, B. C.; Nobrega, C. C.; Correa, J. R.; Silva, R. G.; Oliveira, H. C. B.; Gomes, A. F.; Gozzo, F. C.; Neto, B. A. D. Chem. Eur. J. 2013, 19, 4156–4168; (n) Alvim, H. G. O.; Lima, T. B.; Oliveira, H. C. B.; Gozzo, F. C.; Macedo, J. L.; Abdelnur, P. V.; Silva, W. A.; Neto, B. A. D. ACS Catal. 2013, 3, 1420–1430.
   Web of Science ®Google Scholar
• (a) Bourlinos, A. B.; Raman, K.; Herrera, R.; Zhang, Q.; Archer, L. A.; Giannelis, E. P. J. Am. Chem. Soc. 2004, 126, 15358–15359 (b) Rickert, P. G.; Antonio, M. R.; Firestone, M. A.; Kubatko, K. A.; Szreder, T.; Wishart, J. F.; Dietz, M. L. J. Phys. Chem. B 2007, 111, 4685–4692; (c) Rickert, P. G.; Antonio, M. R.; Firestone, M. A.; Kubatko, K. A.; Szreder, T.; Wishart, J. F.; Dietz, M. L. Dalton Trans. 2007, 529–531.
   PubMed Web of Science ®Google Scholar
• (a) Leng, Y.; Wang, J.; Zhu, D.; Ren, X.; Ge, H.; Shen, L. Angew. Chem. Int. Ed. 2009, 48, 168–171; (b) Zhang, W.; Leng, Y.; Zhu, D.; Wu, Y.; Wang, J. Catal. Commun. 2009, 11, 151–154; (c) Li, H.; Qiao, Y.; Hua, L.; Hou, Z.; Feng, B.; Pan, Z.; Hu, Yu.; Wang, X.; Zhao, X.; Yu, Y. ChemCatChem 2010, 2, 1165–1170; (d) Zhang, W.; Leng, Y.; Zhao, P.; Wang, J.; Zhu, D.; Huang, J. Green Chem. 2011, 13, 832–834; (e) Fang, D.; Wang, F.; Wang, L.; Wu, Y.; Yang, J.; Qian, C. Curr. Catal. 2012, 1, 197–201.
   PubMed Web of Science ®Google Scholar
• (a) Qiao, Y.; Hou, Z.; Li, H.; Hu, Y.; Feng, B.; Wang, X.; Hua, L.; Huang, Q. Green Chem. 2009, 11, 1955–1960; (b) Leng, Y.; Wang, J.; Zhu, D.; Zhang, M.; Zhao, P.; Long, Z.; Huang, J. Green Chem. 2011, 13, 1636–1639; (c) Leng, Y.; Wang, J.; Zhu, D.; Shen, L.; Zhao, P.; Zhang, M. Chem. Eng. J. 2011, 173, 620–626; (d) Leng, Y.; Zhang, W.; Wang, J.; Jiang, P. Appl. Catal. A: Gen. 2012, 445–446, 306–311.
   Web of Science ®Google Scholar
• Van Eldik, R.; Hubbard, C. D. Chemistry under Extreme or Non-classical Conditions; J. Wiley & Sons: New York, 1996.
   Google Scholar
• (a) Lidström, P.; Tierney, J.; Wathey, B.; Westman, J. Tetrahedron 2001, 57, 9225–9283; (b) Larhed, M.; Moberg, C.; Hallberg, A. Acc. Chem. Res. 2002, 35, 717–727; (c) Roberts, B. A.; Strauss, C. R. Acc. Chem. Res. 2005, 38, 653–661; (d) Dallinger, D.; Kappe, C. O. Chem. Rev. 2007, 107, 2563–2591; (e) Polshettiwar, V.; Varma, R. S. Acc. Chem. Res. 2008, 41, 629–639.
   Web of Science ®Google Scholar
• (a) Deshayes, S.; Liagre, M.; Loupy, A.; Luche, J. L.; Petit, A. Tetrahedron 1999, 55, 10851–10870; (b) Kappe, C. O. Curr. Opin. Chem. Biol. 2002, 6, 314–320; (c) Kappe, C. O. Chem. Soc. Rev. 2008, 37, 1127–1139.
   Web of Science ®Google Scholar
• Chen, Z.; Fu, R.; Chai, W.; Zheng, H.; Sun, L.; Lu, Q.; Yuan, R. Tetrahedron 2014, 70, 2237–2245.
   Web of Science ®Google Scholar
• (a) Folkers, K.; Harwood, H. J.; Johnson, T. B. J. Am. Chem. Soc. 1932, 54, 3751–3758; (b) Kappe, C. O. J. Org. Chem. 1997, 62, 7201–7204; (c) Ling, R.; Yoshida, M.; Mariano, P. S. J. Org. Chem. 1996, 61, 4439–4449.
   Web of Science ®Google Scholar