Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 48, 2018 - Issue 14
472
Views
76
CrossRef citations to date
0
Altmetric
Synthetic Communications Reviews

Ultrasound-assisted green synthesis of five-membered O- and S-heterocycles

Pages 1715-1738 | Received 04 Feb 2018, Published online: 18 Jun 2018

References

  • (a) Cox, C. D.; Breslin, M. J.; Mariano B. J. Tetrahedron Lett. 2004, 45, 1489. (b) Trilleras, J.; Polo, E.; Quiroga, J.; Cobo, J.; Nogueras, M. Appl. Sci. 2013, 3, 457. (c) Kaur, N. Catal. Rev. 2015, 57, 478.
  • (a) Kaur, N. J. Iran. Chem. Soc. 2015, 12, 9. (b) Kaur, N. Synth. Commun. 2015, 45, 1269. (c) Kaur, N.; A Kishore; D. Synth. Commun. 2014, 44, 1019. (d) Kaur, N. Synth. Commun. 2014, 44, 3483. (e) Kaur, N. Synth. Commun. 2014, 44, 3509. (f) Kaur, N. Synth. Commun. 2014, 44, 3229. (g) Li, J.-T.; Zhang, X.-H.; Lin, Z.-P. Beilstein J. Org. Chem. 2007, 3, 1. (h) Kaur, N. Mini Rev. Org. Chem. 2017, 14, 3. (i) Dwivedi, J.; Kaur, N.; Kishore, D.; Kumari, S.; Sharma, S. Curr. Top. Med. Chem. 2016, 16, 2884. (j) Kaur, N. J. Heterocycl. Chem. 2015, 52, 953.
  • (a) Li, J.-T.; Yang, W.-Z.; Wang, S.-X.; Li, S.-H.; Li, T.-S. Ultrason. Sonochem. 2009, 9, 237. (b) Sadjadi, S.; Sepehrian, H. Ultrason Sonochem. 2011, 18, 480. (c) Srinivasa, H. T.; Nagarajaiah, H.; Palakshamurthy, B. S.; Hariprasad, S.; Begum, N. S. J. Chem. Sci. 2013, 125, 1079. (d) Kumar, B.; Smita, K.; Kumar, B.; Cumbal, L. J. Chem. Sci. 2014, 126, 1831.
  • (a) Zare, L.; Mahmoodi, N. O.; Yahyazadeh, A.; Nikpassand, M. Ultrason. Sonochem. 2012, 19, 740. (b) Demirbas, N.; Karaogl, U. S. A.; Demirbas, A.; Sancak, K. Eur. J. Med. Chem. 2004, 39, 793.
  • (a) Zou, Y.; Wu, H.; Hu, Y.; Liu, H.; Zhao, X.; Ji, H. L.; Shi, D. Q. Ultrason. Sonochem. 2011, 18, 708. (b) Souldozi, A.; Ramazani, A. Tetrahedron Lett. 2007, 48, 1549. (c) Azarifar, D.; Khatami, S. M.; Nejat-Yami, R. J. Chem. Sci. 2014, 126, 95.
  • (a) Kaur, N. 2014 Inorg. Chem. Commun. 49, 86. (b) Kaur, N. Kishore, D. 2014 Synth. Commun. 44, 1173. (c) Kaur, N. 2015 Synth. Commun. 45, 173. (d) Kaur, N. 2014 Synth. Commun. 44, 3201. (e) Kaur, N. 2015 Synth. Commun. 45, 1. (f) Kaur, N. 2015 Synth. Commun. 45, 35. (g) Li, J. T., Han, J. F., Yang, J. H. and Li, T. S. 2003 Ultrason. Sonochem. 10, 199.
  • Mahdavinia, G. H.; Rostamizadeh, S.; Amani, A. M.; Emdadi, Z. 2009 Ultrason. Sonochem. 16, 7.
  • Duarte, A; Cunico, W; Pereira, C. M. P.; Flores, A. F. C. Freitag, R. A. 2010 Ultrason. Sonochem. 17, 281.
  • Li, J. T.; Meng, X. T.; Zhai, X. L. 2009 Ultrason. Sonochem. 16, 590.
  • Sreedhar, B.; Reddy, P. S. 2007 Synth. Commun. 37, 805.
  • (a) Nuchter, M; Ondruschka, B; Jungnickel, A.; Muller, U. 2000 J. Phys. Org. Chem. 13, 579. (b) Kaur, B Kumar, H. 2013 J. Chem. Sci. 125, 989.
  • (a) Ji, S. J.; Shen, Z. L.; Gu, D. G.; Huang, X Y. 2005 Ultrason. Sonochem. 12, 161. (b) Kaur, N. 2015 Syn. Commun. 45, 909. (c) Kaur, N. 2015 Synth. Commun. 45, 151. (d) Kaur, N. 2015 Synth. Commun. 45, 1379. (e) Kaur, N. 2015 Synth. Commun. 45, 1145. (f) Kaur, N. 2015 Synth. Commun. 45, 300. (g) Kaur, N.; Kishore, D. 2014 Synth. Commun. 44, 1375.
  • (a) Li, J. T.; Yin, Y.; Li, L.; Sun, M. X. 2010 Ultrason. Sonochem. 17, 11. (b) Azarifar, D.; Soleimanei, F. Jaleh, B. 2013 J. Chem. Sci. 125, 819.
  • (a) Pizzuti, L.; Martins, P. L. G.; Ribeiro, B. A.; Quina, F. H.; Pinto, E.; Flores, A. F. C.; Venzke, D. Pereira, C. M. P. 2010 Ultrason. Sonochem. 17, 34. (b) Lv, G.-S.; Junduan, F.; Ding, J.-C.; Cheng, T.-X.; Gao, W.-X.; Chen, J.-X. Wu, H.-Y. 2012 J. Chem. Sci. 124, 1057.
  • Juarez, R.; Concepcion, P.; Corma, A.; Garcia, H. 2010 Chem. Commun. 46, 4181.
  • Cravotto, G.; Cintas, P. 2006 Chem. Soc. Rev. 35, 180.
  • Barros, C. J. P.; de Freitas, J. R.; de Oliveira, R. N.; de Freitas Filho, J. R. 2011 J. Chil. Chem. Soc. 56, 610.
  • (a) Kaur, N. 2015 Syn. Commun. 45, 789. (b) Kaur, N. 2015 Synth. Commun. 45, 432. (c) Kaur, N. 2014 J. Iranian Chem. Soc. 11, 523. (d) Kaur, N. 2015 Synth. Commun. 45, 273. (e) Kaur, N. 2015 Synth. Commun. 45, 1493. (f) Kaur, N. 2015 Synth. Commun. 45, 1599. (g) Kaur, N. 2015 Synth. Commun. 45, 1711. (h) Cintas, P; Palmisano, G Cravoto, G. 2011 Ultrason. Sonochem. 18, 836.
  • Dadhania, A. N.; Patel, V. K. Raval, D. K. 2011 J. Braz. Chem. Soc. 22, 511.
  • Franco, C. F. J.; Jordao, A. K.; Ferreira, V. F.; Pinto, A. C.; de Souza, M. C. B. V.; Resende, J. A. and Cunha, A. C. 2011 J. Braz. Chem. Soc. 22, 187.
  • Jiang, Y; Chen, X; Qu, L; Wang, J; Yuan, J; Chen, S; Li, X.; Qu, C. 2011 Ultrason. Sonochem. 18, 527.
  • Martings, M. A.; Pereira, C. M.; Cunico, W. M. S.; Rosa, F. A.; Peres, R. L.; Machado, P; Zanatta, N.; Bonacorso, H. G. 2006 Ultrason. Sonochem. 13, 364.
  • (a) Kaur, N. 2015 Catal. Rev. 57, 1. (b) Kaur, N. 2015 Synth. Commun. 45, 539. (c) Kaur, N.; Kishore, D. 2014 Synth. Commun. 44, 3047. (d) Kaur, N Kishore, D. 2014 Synth. Commun. 44, 2615. (e) Kaur, N.; Kishore, D. 2014 Synth. Commun. 44, 2739. (f) Ji, S. J.; Wang, S. Y. 2005 Ultrason. Sonochem. 12, 339.
  • (a) Shen, Z. L.; Ji, S. J.; Wang, S. Y.; Zeng, X. F. 2005 Tetrahedron, 61, 10552. (b) Ruiz, E.; Rodriguez, H.; Coro, J.; Salfran, E.; Suarez, M.; Martinez-Alvarez, R. Martin, N. 2011 Ultrason Sonochem. 18, 32.
  • Cella, R.; Stefani, H. A. 2009 Tetrahedron, 65, 2619.
  • (a) Kaur, N. J. Heterocycl. Chem. 2015, 52, 953. (b) Kaur, N. Curr. Org. Synth. 2017, 14, 531. (c) Kaur, N. Curr. Org. Synth. 2017, 14, 972. (d) Kaur, N. Mini Rev. Org. Chem. 2017, 14, 3. (e) Kaur, N. Synth. React. Inorg. Met. Org. Nano-Met. Chem. 2016, 46, 983. (f) Kaur, N. Inorg. Nano-Met. Chem. 2017, 47, 163. (g) Capello, C.; Fischer, U.; Hungerbuhler, K. Green Chem. 2007, 9, 927. (h) Pizzuti, L.; Franco, M. S. F.; Flores, A. F. C.; Quina, F. H.; Pereira, C. M. P. Recent Advances in the Ultrasound-Assisted Synthesis of Azoles. In Green Chemistry – Environmentally Benign Approaches, Kidwai M. Ed., InTech, 2012, pp 81–102. http://www.intechopen.com/books/green-chemistry-environmentally-benign-approaches/recent-advances-inthe-ultrasound-assisted-synthesis-of-azoles.
  • Mason, T. J. 2007 Ultrason. Sonochem. 14, 476.
  • (a) Xu, H.; Liao, W. M.; Li, H. F. 2007 Ultrason. Sonochem. 14, 779. (b) Kaur, N. 2015 Syn. Commun. 45, 403. (c) Kaur, N.; Kishore, D. 2014 Synth. Commun. 44, 3082. (d) Kaur, N.; Kishore, D. 2014 Synth. Commun. 44, 2577. (e) Kaur, N.; Dwivedi, J.; Kishore, D. 2014 Synth. Commun. 44, 1671.
  • Guzen, K. P.; Guarezemini, A. S.; Orfao, A. T. G.; Cella, R.; Pereira, C. M. P. Stefani, P. H. A. 2007 Tetrahedron Lett. 48, 1845.
  • Saleh, T. S.; El-Rahman, N. M. A.; Elkateb, A. A.; Shaker, N. O.; Mahmoud, N. A. Gabal, S. A. 2012 Ultrason. Sonochem. 19, 491.
  • Zhang, Z.-H.; Li, J.-J. Li, T.-S. 2012 Ultrason. Sonochem. 19, 264.
  • Nagargoje, D.; Mandhane, P.; Shingote, S.; Badadhe, P.; Gill, C. 2012 Ultrason. Sonochem. 19, 94.
  • Dabiri, M.; Noroozi Tisseh, Z.; Bahramnejad, M.; Bazgir, A. 2011 Ultrason. Sonochem. 18, 1153.
  • Prasad, J. V.; Reddy, J. S.; Kumar, N. R.; Solomon, K. A.; Gopikrishna, G. 2011 J. Chem. Sci. 123, 673.
  • Zhang, Z. H.; Li, J.; Li, T. S. 2008 Ultrason. Sonochem. 15, 673.
  • (a) Bazgir, A.; Ahadi, S.; Ghahremanzadeh, R.; Khavasi, H. R. Mirzaei, P. 2010 Ultrason. Sonochem. 17, 447. (b) Satyanarayana, V. S. V. Sivakumar, A. 2011 Ultrason. Sonochem. 18, 917.
  • (a) Rouhani, M.; Ramazani, A.; Joo, S. W. Hanifehpour, Y. 2012 Bull. Korean Chem. Soc. 33, 4127. (b) Rouhani, M.; Ramazani, A. Joo, S. W. 2014 Ultrasonics Sonochem. 21, 262.
  • Stoermer, R. 1900 Justus Liebigs Ann. Chem. 312, 237.
  • Gao, W.; Zheng, M.; Li, Y. 2011 J. Org. Chem. 7, 1533.
  • Li, Y.; Yan, Y.; Gao, W. 2012 Heterocycles 85, 421.
  • Wunsch, K. H.; Boulton, A. J. 1969 Adv. Heterocycl. Chem. 8, 303.
  • Heller, G. 1908 J. Prakt. Chem. 77, 145.
  • Faltsiand, F.; Kloiber, F. 1929 Monatsh. Chem. 53/54, 620.
  • Scholl, R. 1913 Monatsh. Chem. 34, 1011.
  • Davis, R. B.; Pizzini, L. C. 1960 J. Org. Chem. 25, 1884.
  • Safaei-Ghomi, J.; Fadaeian, M.; Hatami, A. 2007 Turk. J. Chem. 31, 89.
  • Abdel-Rahman, N. M.; Saleh, T. S.; Mady, M. F. 2009 Ultrason. Sonochem. 16, 70.
  • Silva, F. A. N.; Galluzzi, M. P.; Albuquerque, B.; Pizzuti, L.; Gressler, V.; Rivelli, D. P.; Barros, S. B. M.; Pereira, C. M. P. 2009 Lett. Drug. Des. Dis. 6, 323.
  • Li, J.-T.; Zhai, X.-L.; Chen, G.-F. 2010 Ultrason. Sonochem. 17, 356.
  • Tiwari, V.; Parvez, A.; Meshram, J. 2011 Ultrason. Sonochem. 18, 911.
  • Kaur, N. 2018 Synth. Commun. 48, 1235.
  • Pfoertner, K.-H.; Bernauer, K.; Kaufmann, F. and Lorch, E. 1985 Helv. Chim. Acta. 68, 584.
  • Pfoertner, K.-H.; Montavon, F.; Bernauer, K. 1985 Helv. Chim. Acta. 68, 600.
  • Hassner, A.; Amarasekara, A. S.; Andisik, D. 1988 J. Org. Chem. 53, 27.
  • Maga, J. A. J. 1978 J. Agric. Food Chem. 26, 1049.
  • Saa, M. C. M.; Kascheres, A. 1996 J. Org. Chem. 61, 3749.
  • Pinho Melo, T. M. V. D.; Lopes, C. S. J.; Rocha Gonsalves, A. M. A. 2000 Tetrahedron. Lett. 41, 7217.
  • Mirkhani, V.; Moghadam, M.; Tangestaninejad, S.; Mohammadpoor-Baltork, I.; Mahdavi, M. 2009 Monatshefte. Für. Chemie. 140, 1489.
  • Mason, T. J.; Luche, J.-L.; Eldick, R. V.; Hubbard, C. D. Chemistry under Extreme or Non-Classical Conditions; Wiley: New York, 1997; p 317.
  • Suslick, K. S. Ultrasound, its Chemical, Physical and Biological Effect; VCH: Weinheim, 1988; p. 165.
  • Moghadam, M.; Mirkhani, V.; Tangestaninejad, S.; Mohammadpoor-Baltork, I.; Kargar, H. 2009 J. Iran. Chem. Soc. 6, 251.
  • Desimoni, G.; Faita, G.; Jorgensen, K. A. 2006 Chem. Rev. 106, 3561.
  • Bower, J. F.; Martin, C. J.; Rawson, D. J.; Slawin, A. M. Z.; Williams, J. M. J. 1996 J. Chem. Soc. Perkin Trans. 1, 333.
  • Beccalli, E. M.; Broggini, G. 2003 Tetrahedron. Lett. 44, 1919.
  • Abbiati, G.; Beccalli, E. M.; Broggini, G.; Zoni, C. 2003 J. Org. Chem. 68, 7625.
  • Beccalli, E. M.; Broggini, G.; Paladino, G.; Penoni, A.; Zoni, C. 2004 J. Org. Chem. 69, 5627.
  • Beccalli, E. M.; Broggini, G.; Martinelli, M.; Paladino, G. 2005 Tetrahedron. 61, 1077.
  • Abbiati, G.; Beccalli, E. M.; Broggini, G.; Martinelli, M.; Paladino, G. 2006 Synlett. 1, 73.
  • Beccalli, E. M.; Borsini, E.; Broggini, G.; Palmisano, G.; Sottocornola, S. 2008 J. Org. Chem. 73, 4746.
  • Elguero, J.; Goya, P.; Jagerovic, N.; Silva, A. M. S. 2002 Italian Soc. Chem. 6, 167.
  • Bretanha, L. C.; Teixeira, V. E.; Ritter, M.; Siqueira, G. M.; Cunico, W.; Pereira, C. M. P.; Freitag, R. A. 2011 Ultrason. Sonochem. 18, 704.
  • Bello Forero, J. S.; De Carvalho, E. M.; Jones Jr. J.; Da Silva, F. M. 2011 Heterocyclic Lett. 1, 61.
  • Pett, N. P.; Sunder, S.; Barbuch, R. J. 1986 J. Heterocycl. Chem. 23, 129.
  • dos Santos, B. D. de C. F.; Forero, J S. B; Carvalho, E. M.; Junior, J. and da Silva, F. M. 2012 Heterocycl. Lett. 2, 31.
  • Chou, T. S.; Tsai, C. Y. 1991 J. Chem. Soc. Chem. Commun. 1287.
  • Chou, T. S.; Chang, R. C. 1992 J. Chem. Soc. Chem. Commun. 549.
  • Chou, T. S.; Tsai, C. Y. 1992 Heterocycles. 34, 663.
  • Lee, S. J.; Chou, T. S.; Peng, M. L. and Ho, W. H. 1988 Bull. Inst. Chem. Acad. Sin. 35, 1.
  • Chou, T.-S.; Tsai, C.-Y. 1993 J. Chin. Chem. Soc. 40, 581.
  • Noei, J.; Khosropour, A. R. 2009 Ultrason. Sonochem. 16, 711.
  • Eicher, T.; Hauptmann, S. The Chemistry of Heterocycles; 2nd ed.; Wiley-VCH: Saarbruckene Leipzig, 2003; p 154.
  • Gupta, R.; Gupta, N.; Jain, A. 2010 Indian J. Chem. 49B, 351.
  • Venzke, D.; Flores, A. F. C.; Quina, F. H.; Pizzuti, L.; Pereira, C. M. P. 2011 Ultrason. Sonochem. 18, 370.
  • Mamaghani, M.; Loghmanifar, A.; Taati, M. R. 2011 Ultrason. Sonochem. 18, 45.
  • Neuenfeldt, P. D.; Duval, A. R.; Drawanz, B.; Rosales, P. F.; Gomes, C. R. B.; Pereira, C. M. P.; Cunico, W. 2011 Ultrason. Sonochem. 18, 65.
  • Dandia, A.; Singh, R.; Bhaskaran, S.; Samant, S. D. 2011 Green Chem. 13, 1852.
  • Yuan, Y.-Q.; Guo, S.-R. 2011 Synth. Commun. 41, 2169.
  • Metwally, M. A.; Abdel-latif, E.; Amer, F. A.; Kaupp, G. 2004 Dyes. Pigm., 60, 249.
  • Metwally, M. A.; Abdel-Latif, E.; Amer, F. A. 2001 J. Text. Assoc. 63, 155.
  • Gomha, S. M.; Khalil, K. D. 2012 Molecules. 17, 9335.
  • (a) Darehkordi, A.; Ghazi, S. 2013 J. Chem. 1. (b) Sadjadi, S.; Sepehrian, H. 2011 Ultrason Sonochem. 18, 480.
  • Shinde, A. D.; Shingate, B. B.; Shingare, M. S. 2010 Phosphorus. Sulfur. Silicon. Relat. Elem. 185, 1594.
  • (a) Feng, H.; Ying, X.; Peng, Y.; Van der Eycken, E. V.; Liu, C.; Zhao, S.; Song, G. 2013 Monatsh. Chem. 144, 681. (b) Peng, Y.; Song, G. 2001 Green. Chem. 3, 302.
  • Padmaja, A.; Rajasekhar, C.; Muralikrishna, A.; Padmavathi, V. 2012 J. Chem. Pharm. Res. 4, 294.
  • Chohan, Z. H.; Pervez, H.; Rauf, A.; Andrea, S.; Supuran, C. T. 2002 J. Enzym. Inhib. Med. Chem. 17, 117.
  • Bonizzoni, M.; Fabbrizzi, L.; Taglietti, A. 2006 Eur. J. Org. Chem. 3567.
  • Rostamizadeh, S.; Aryan, R.; Ghaieni, H. R. 2008 Heteroatom. Chem. 19, 320.
  • Shinde, A. D.; Sonar, S. S.; Shingate, B. B.; Shingare, M. S. 2010 Phosphorus. Sulfur. Silicon. Relat. Elem. 185, 1594.
  • Shelke, S.; Mhaske, G.; Gadakh, S.; Gill, C. 2010 Bioorg. Med. Chem. Lett. 20, 7200.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.