Mahshid RAHIMIFARD, Ghodsi MOHAMMADI ZIARANI

Application of guanidine and its salts in multicomponent reactions

This review gives an overview of the application of guanidine and its salts in multicomponent reactions. It can act as a catalyst or solvent for multicomponent reactions or as a reagent for synthesis of substituted diazines, triazines, and macroheterocycles by multicomponent reactions.

Anahtar Kelimeler:

Guanidine, guanidinium salt, multicomponent reaction, pyrimidine, pyrimidinone, triazine

Application of guanidine and its salts in multicomponent reactions

Keywords:

Guanidine, guanidinium salt, multicomponent reaction, pyrimidine, pyrimidinone, triazine,

PDF

___

Wyss, P. C.; Gerber, P.; Hartman, P. G.; Hubschwerlen, C.; Locher, H.; Marty, H. P.; Stahl, M. J. Med. Chem. 2003, 46, 2304–2312.
Joffe, A. M.; Farley, J. D.; Linden, D.; Goldsand, G. Am. J. Med. 1989, 87, 332–338.
Petersen, E.; Schmidt, D. R. Exp. Rev. Anti. Infect. Ther. 2003, 1, 175–182.
Nadal, E.; Olavarria, E. Int. J. Clin. Pract. 2004, 58, 511–516.
Schmidtchen, F. P.; Berger, M. Chem. Rev. 1997, 97, 1609–1646.
Ube, H.; Uraguchi, D.; Terada, M. J. Organomet. Chem. 2007, 692, 545–549.
Weber, L. Drug Discov. Today 2002, 7, 143–147.
Domling, A. Curr. Opin. Chem. Biol. 2002, 6, 306–313.
Otzen, T.; Wempe, E. G.; Kunz, B.; Bartels, R.; Lehwark-Yvetot, G.; H¨ ansel, W.; Schaper, K. J.; Seydel, J. K. J. Med. Chem. 2004, 47, 240–253.
Peters, J. U.; Hunziker, D.; Fischer, H.; Kansy, M.; Weber, S.; Kritter, S.; M¨ uller, A.; Wallier, A.; Ricklin, F.; Boehringer, M.; et al. Bioorg. Med. Chem. Lett. 2004, 14, 3575–3578.
Wyatt, E. E.; Galloway, W. R. J. D.; Thomas, G. L.; Welch, M.; Loiseleur, O.; Plowright, A. T.; Spring, D. R. Chem. Commun. 2008, 4962–4964.
Heravi, M. M.; Zakeri, M.; Mohammadi, N. Chinese Chem. Lett. 2011, 22, 797–800.
Heydari, A.; Arefi, A.; Khaksar, S.; Shiroodi, R. K. J. Mol. Catal. A: Chem. 2007, 271, 142–144.
Zhuang, Q.; Han, H. X.; Wang, S.; Tu, S.; Rong, L. Synth. Commun. 2009, 39, 516–522.
Jawale, D. V.; Pratap, U. R.; Netankar, P. D.; Mane, R. A. Chem. Biol. Interface 2012, 2, 420–425.
Tao, S.; Xia, S.; Rong, L.; Cao, C.; Tu, S. Res. Chem. Intermed. 2012, 38, 2065–2073.
Rong, L.; Ji, H.; Xia, S.; Yin, S.; Shi, Y.; Tu, S. J. Heterocycl. Chem. 2012, 49, 696–699.
Vanden, E.; Jean, J.; Hecq, N.; Kataeva, O.; Kappe, C. O. Tetrahedron 2001, 57, 1785–1791.
Wyatt, E. E.; Fergus, S.; Galloway, W. R. J. D.; Bender, A.; Fox, D. J.; Plowright, A. T.; Jessiman, A. S.; Welch, M.; Spring, D. R. Chem. Commun. 2006, 3296–3298.
Gangjee, A.; Adair, O.; Queener, S. F. J. Med. Chem. 1999, 42, 2447–2455.
Gangjee, A.; Vasudevan, A.; Queener, S. F.; Kisliuk, R. L. J. Med. Chem. 1996, 39, 1438–1446.
Hamby, J. M.; Connolly, C. J. C.; Schroeder, M. C.; Winters, R. T.; Showalter, H. D. H.; Panek, R. L.; Terry, C.; Olsewski, B.; Ryan, M. J.; Dahring, T. J. Med. Chem. 1997, 40, 2296–2303. Nasr, M. N.; Gineinah, M. M. Arch. Pharm. 2002, 335, 289–295. Mont, N.; Teixid´ o, J.; Borrell, J. I.; Kappe, C. O. Tetrahedron Lett. 2003, 44, 5385–5387.
Mont, N.; Teixid´ o, J.; Kappe, C. O.; Borrell, J. I. Mol. Divers. 2003, 7, 153–159.
Victory, P.; Borrell, J. I. Trends Heterocycl. Chem. 1993, 3, 235–247. Victory, P. J.; Teixid´ o, J.; Borrell, J. I. Heterocycles 1992, 34, 1905–1916. Borrell, J. I.; Teixid´ o, J.; Matallana, J. L.; Mart´ınez-Teipel, B.; Colominas, C.; Costa, M.; Balcells, M.; Schuler, E.; Castillo, M. J. J. Med. Chem. 2001, 44, 2366–2369. Borrell, J. I.; Teixid´ o, J.; Mart´ınez-Teipel, B.; Serra, B.; Matallana, J. L.; Costa, M.; Batllori, X. Collect. Czech. Chem. Commun. 1996, 61, 901–909.
Berzosa, X.; Bellatriu, X.; Teixido, J.; Borrell, J. I. J. Org. Chem. 2009, 75, 487–490.
Galve, I.; Puig de la Bellacasa, R.; S´ anchez-Garc´ıa, D.; Batllori, X.; Teixid´ o, J.; Borrell, J. Mol. Divers. 2012, 16, 639–649.
Jin, G.; Wu, C. C. N.; Carson, D. A.; Cottam, H. B. Nucleos. Nucleot. Nucl. 2006, 25, 1391–1397.
Rong, L.; Han, H.; Wang, H.; Jiang, H.; Tu, S.; Shi, D. J. Heterocycl. Chem. 2009, 46, 152–157.
Augustin, M.; Groth, C. H. J. Prakt. Chem. 1979, 321, 215–225.
Tominaga, Y.; Hirose, M.; Hagimori, M.; Shigemitsu, Y.; Mizuyama, N.; Wang, B. C. Heterocycles 2009, 78, 899–903.
Matasi, J. J.; Caldwell, J. P.; Hao, J.; Neustadt, B.; Arik, L.; Foster, C. J.; Lachowicz, J.; Tulshian, D. B. Bioorg. Med. Chem. Lett. 2005, 15, 1333–1336.
Meshram, G.; Wagh, P.; Deshpande, S.; Amratlal, V. Lett. Org. Chem. 2013, 10, 445–450.
Yadav, L. D. S.; Rai, A. Carbohydr. Res. 2009, 344, 2329–2335.
Yadav, L. D. S.; Rai, A. Synthesis 2009, 2009, 2802–2808.
Trivedi, A.; Dodiya, D.; Surani, J.; Jarsania, S.; Mathukiya, H.; Ravat, N.; Shah, V. Arch. Pharm. 2008, 341, 435–439.
Bararjanian, M.; Balalaie, S.; Rominger, F.; Barouti, S. Helv. Chim. Acta. 2010, 93, 777–784.
Liu, L.; Yin, S.; Xia, S.; Cai, P.; Rong, L. Chinese J. Org. Chem. 2012, 32, 612–615.
Bhatewara, A.; Jetti, S. R.; Kadre, T.; Paliwal, P.; Jain, S. Arch. Appl. Sci. Res. 2012, 4, 1274–1278.
Bhatewara, A.; Jetti, S. R.; Kadre, T.; Paliwal, P.; Jain, S. Int. J. Med. Chem. 2013, 2013, 1–5.
Deshmukh, M. B.; Salunkhe, S. M.; Patil, D. R.; Anbhule, P. V. Eur. J. Med. Chem. 2009, 44, 2651–2654.
Val, C.; Crespo, A.; Yaziji, V.; Coelho, A.; Azuaje, J.; El Maatougui, A.; Carbajales, C.; Sotelo, E. ACS Comb. Sci. 2013, 15, 370–378.
Ali, K. A. Heterocycles 2012, 85, 1975–1986.
Rong, L.; Han, H.; Gao, L.; Dai, Y.; Cao, M.; Tu, S. Synth. Commun. 2010, 40, 504–509.
Hekmatshoar, R.; Kenary, G. N.; Sadjadi, S.; Beheshtiha, Y. S. Synth. Commun. 2010, 40, 2007–2013.
Ahmadi, S.; Sadjadi, S.; Hosseinpour, M. Monatsh. Chem. 2011, 142, 1163–1168.
Deshmukh, M. B.; Anbhule, P. V.; Jadhav, S. D.; Jagtap, S. S.; Patil, D. R.; Salunkhe, S. M.; Sankpal, S. A. Indian J. Chem. B 2008, 47, 792.
Sheibani, H.; Saljoogi, A. S.; Bazgir, A. Arkivoc 2008, 2, 115–123.
Sheibani, H.; Seifi, M.; Bazgir, A. Synth. Commun. 2009, 39, 1055–1064.
Raghuvanshi, D. S.; Singh, K. N. J. Heterocycl. Chem. 2011, 48, 582–585.
Tominaga, Y.; Shigemitsu, Y.; Sasaki, K. J. Heterocycl. Chem. 2002, 39, 571–591.
Tominaga, Y.; Matsuda, Y. J. Heterocycl. Chem. 1985, 22, 937–949. Ramezanpour, S.; Hashtroudi, M. S.; Bijanzadeh, H. R.; Balalaie, S. Tetrahedron Lett. 2008, 49, 3980–3982. Amutha, P.; Nagarajan, S. Helv. Chim. Acta. 2010, 93, 430–434.
Maddila, S.; Jonnalagadda, S. B.; Chunduri, V.; Lavanya, P. Heterocycl. Lett. 2012, 2, 37–42.
Ostras, K. S.; Gorobets, N. Y.; Desenko, S. M.; Musatov, V. I. Mol. Divers. 2006, 10, 483–489. Mohammadnejad, M.; Hashtroudi, M. S.; Balalaie, S. Heterocycl. Commun. 2009, 15, 459–466. Mirza-Aghayan, M.; Baie Lashaki, T.; Rahimifard, M.; Boukherroub, R.; Tarlani, A. A. J. Iran. Chem. Soc. 2011, 8, 280–286. Akbas, E.; Levent, A.; Guemues, S.; Suemer, M. R.; Akyazi, I. Bull. Korean Chem. Soc. 2010, 31, 3632–3638.
Prakash, O.; Pannu, K.; Naithani, R.; Kaur, H. Synth. Commun. 2006, 36, 3479–3485.
Trivedi, A. R.; Bhuva, V. R.; Dholariya, B. H.; Dodiya, D. K.; Kataria, V. B.; Shah, V. H. Bioorg. Med. Chem. Lett. 2010, 20, 6100–6102.
Lokwani, D.; Shah, R.; Mokale, S.; Shastry, P.; Shinde, D. J. Comput. Aided Mol. Des. 2012, 26, 267–277.
Azizian, J.; Mirza, B.; Mojtahedi, M. M.; Abaee, M. S.; Sargordan, M. J. Fluorine Chem. 2008, 129, 1083–1089. Azizian, J.; Mohammadi, M. K.; Firuzi, O.; Mirza, B.; Miri, R. Chem. Biol. Drug Des. 2010, 75, 375–380.
Chavda, D. R.; Modiya, P. R.; Marvaniya, H. M.; Sen, D. J. Int. J. Drug Dev. Res. 2010, 2, 348–355.
Ujjinamatada, R. K.; Hosmane, R. S. Tetrahedron Lett. 2005, 46, 6005–6009.
Gund, P.; Berkelhammer, G.; Wayne, R. S. Tetrahedron Lett. 1972, 13, 3983–3986.
Zomordbakhsh, S.; Anaraki-Ardakani, H.; Zeeb, M.; Sadeghi, M.; Mazraeh-Seffid, M. J. Chem. Res. 2012, 36, 138–140.
Jalani, H. B.; Pandya, A. N.; Pandya, D. H.; Sharma, J. A.; Sudarsanam, V.; Vasu, K. K. Tetrahedron Lett. 2013, 54, 5403–5406.
Jalani, H. B.; Sudarsanam, V.; Vasu, K. K. Synthesis 2012, 44, 3378–3386.
Yavari, I.; Aminkhani, A.; Arab-Salmanabadi, S. Monatsh. Chem. 2012, 143, 1195–1198.
Kolos, N. N.; Chechina, N. V.; Zamigailo, L. L.; Vashchenko, E. V. Chem. Heterocycl. Comp. 2013, 49, 872–881. Akhmetova, V. R.; Khairullina, R. R.; Bushmarinov, I. S.; Tyumkina, T. V.; Yanybin, V. M. Arkivoc 2011, 2011, 149–162.
Hieu, C.; Anh, L.; Levov, A. N.; Nikitina, E. V.; Soldatenkov, A. T. Chem. Heterocycl. Comp. 2009, 45, 1406–1407. Baghbanian, S. M.; Khaksar, S.; Vahdat, S. M.; Farhang, M.; Tajbakhsh, M. Chinese Chem. Lett. 2010, 21, 563–567.
Dandia, A.; Jain, A. K.; Sharma, S. Tetrahedron Lett. 2012, 53, 5859–5863.