A novel one-pot three component approach to 6-substituted 2,4- diamino-1,3,5-triazines using nano-sized copper/zinc-modified MCM-41 (Cu/Zn-MCM-41) as a new heterogeneous mesoporous catalyst

Mohsen Shekouhy; Ali Moaddeli; Ali Khalafi-Nezhad

Journal of Industrial and Engineering Chemistry, Vol.50, 41-49, June, 2017

DOI10.1016/j.jiec.2017.01.001 Export Citation

A novel one-pot three component approach to 6-substituted 2,4- diamino-1,3,5-triazines using nano-sized copper/zinc-modified MCM-41 (Cu/Zn-MCM-41) as a new heterogeneous mesoporous catalyst

Mohsen Shekouhy, Ali Moaddeli, and Ali Khalafi-Nezhad^†

Department of Chemistry, College of Sciences, Shiraz University, Shiraz 71454, Iran

E-mail:

The nano-sized copper/zinc-modified MCM-41 (Cu/Zn-MCM-41) was successfully prepared and applied as a new heterogeneous mesoporous nano-catalyst in a more benign and novel one-pot three component strategy for the synthesis of 6-substituted 2,4-diamino-1,3,5-triazines from aryl-aldehydes, hydroxyl-amine and 2-cyanoguanidine under microwave irradiation. Using this method, the major problems of previously reported methods (very low diversity of available starting materials and the production of explosive byproducts) have been solved and all desired products were obtained in good to excellent yields in very short times.

Keywords:6-Substituted 2,4-diamino-1,3,5-triazine;Nano-sized copper/zinc-modified MCM-41;Mesoporous catalyst;Multi-component reaction;One-pot synthesis

[References]

(a)Katritzky AR, Ress CW, Scriven EFV (Eds.), Comprehensive Heterocyclic Chemistry II, 1.9, Pergamon, Oxford, UK, 1996.
Kirsch G, Hesse S, Comel A, Curr. Org. Synth., 1, 47 (2004)
Druzhinin SV, Balenkova ES, Nenajdenko VG, Tetrahedron, 63, 7753 (2007)
Martins MAP, Frizzo CP, Moreira DN, Zanatta N, Bonacorso HG, Chem. Rev., 108(6), 2015 (2008)
Balaban AT, Oniciu DC, Katritzky AR, Chem. Rev., 104(5), 2777 (2004)
Masatane K, Yutaka TJ, J. Heterocycl. Chem., 18, 709 (1981)
Anastas PT, Warner JC, Green Chemistry: Theory and Practice, Oxford University Press, Oxford, 1998.
Saczewski F, Bulakowska A, Bednarski P, Grunert R, Eur. J. Med. Chem., 41, 219 (2006)
Agarwal A, Srivastava K, Puri SK, Chauhan PMS, Bioorg. Med. Chem. Lett., 15, 531 (2005)
Solankee A, Kapadia K, Ciric A, Sokovic M, Doytchinova I, Eur. J. Med. Chem., 45, 510 (2010)
Patel RV, Kumari P, Rajani DP, Pannecouque C, DeClercq E, Chikhalia KH, Future Med. Chem., 4, 1053 (2012)
Zacharie B, Abbott SD, Bienvenu JF, Cameron AD, Cloutier J, Duceppe J, Ezzitouni A, Fortin D, Houde K, Lauzon C, Moreau N, Perron V, Wilb N, Asselin M, Doucet A, Fafard ME, Gaudreau D, Grouix B, Bournet FS, St- Amant N, Gagnon N, Gagnon L, Penney CL, J. Med. Chem., 53, 1138 (2010)
Beijer FH, Kooijiman H, Spek AL, Sijbesma RP, Meijer EW, Angew. Chem.-Int. Edit., 37, 75 (1998)
Pozharskii AF, Soldatenkov AT, Katritzky AR, Heterocycles in Life and Society, Wiley, Chichester, 1997.
Smolin EM, Rapoport L, s-Triazines and Derivatives, Interscience, New York, 1959, pp. 217.268 (Chapter IV).
Shie J, Fang J, J. Org. Chem., 72, 3141 (2007)
Cheng T, Zhang D, Li H, Liu G, Green Chem., 16, 3401 (2014)
Heitbaum M, Glorius F, Escher I, Angew. Chem.-Int. Edit., 45, 4732 (2006)
Ngo H, Lin W, Top. Catal., 34, 85 (2005)
Thomas JM, Raja R, Acc. Chem. Res., 41, 708 (2008)
Abdollahi-Alibeik M, Rezaeipoor-Anari A, Catal. Sci. Technol., 4, 1151 (2014)
Abdollahi-Alibeik M, Pouriayevali M, Catal. Commun., 22, 13 (2012)
Chakraborty B, Viswanathan B, Catal. Today, 49(1-3), 253 (1999)
Demel J, Cejka J, Stepnicka P, J. Mol. Catal. A-Chem., 274(1-2), 127 (2007)
Juan JC, Zhang JC, Yarmo MA, J. Mol. Catal. A-Chem., 267(1-2), 265 (2007)
Al-Hazmi MH, Apblett AW, Catal. Sci. Technol., 1, 621 (2011)
Jiang CW, Zhong X, Luo ZH, RSC Adv., 4, 15216 (2014)
Dong X, Hui Y, Xie X, Zhang P, Zhou G, Xie Z, RSC Adv., 3, 3222 (2013)
Farzaneh F, Zamanifar E, Williams CD, J. Mol. Catal. A-Chem., 218(2), 203 (2004)
Choi JS, Yoon SS, Jang SH, Ahn WS, Catal. Today, 111(3-4), 280 (2006)
Wang LP, Kong AG, Chen B, Ding HM, Shan YK, He MY, J. Mol. Catal. A-Chem., 230(1-2), 143 (2005)
Vetrivel S, Pandurangan A, J. Mol. Catal. A-Chem., 227(1-2), 269 (2005)
Cortes Corberan V, Jia MJ, El-Haskouri J, Valenzuela RX, Beltran-Porter D, Amoros P, Catal. Today, 91, 127 (2004)
Szegedi A, Popova M, Mavrodinova V, Urban M, Kiricsi I, Minchev C, Microporous Mesoporous Mater., 99, 149 (2007)
Higashimoto S, Hu Y, Tsumura R, Iino K, Matsuoka M, Yamashita H, Shul YG, Che M, Anpo M, J. Catal., 235(2), 272 (2005)
Abdollahi-Alibeika M, Moaddeli A, New J. Chem., 39, 2116 (2015)
Shekouhy M, Khalafi-Nezhad A, Green Chem., 17, 4815 (2015)
Zare A, Parhami A, Moosavi-Zare AR, Hasaninejad A, Khalafi-Nezhad A, Beyzavi MH, Can. J. Chem., 87, 416 (2009)
Cooke G, Cremiers HA, Rotello VM, Tarbit B, Tetrahedron, 57, 2787 (2001)

[Referenced By]

[1] (a)Katritzky AR, Ress CW, Scriven EFV (Eds.), Comprehensive Heterocyclic Chemistry II, 1.9, Pergamon, Oxford, UK, 1996.

[2] Kirsch G, Hesse S, Comel A, Curr. Org. Synth., 1, 47 (2004)

[3] Druzhinin SV, Balenkova ES, Nenajdenko VG, Tetrahedron, 63, 7753 (2007)

[4] Martins MAP, Frizzo CP, Moreira DN, Zanatta N, Bonacorso HG, Chem. Rev., 108(6), 2015 (2008)

[5] Balaban AT, Oniciu DC, Katritzky AR, Chem. Rev., 104(5), 2777 (2004)

[6] Masatane K, Yutaka TJ, J. Heterocycl. Chem., 18, 709 (1981)

[7] Anastas PT, Warner JC, Green Chemistry: Theory and Practice, Oxford University Press, Oxford, 1998.

[8] Saczewski F, Bulakowska A, Bednarski P, Grunert R, Eur. J. Med. Chem., 41, 219 (2006)

[9] Agarwal A, Srivastava K, Puri SK, Chauhan PMS, Bioorg. Med. Chem. Lett., 15, 531 (2005)

[10] Solankee A, Kapadia K, Ciric A, Sokovic M, Doytchinova I, Eur. J. Med. Chem., 45, 510 (2010)

[11] Patel RV, Kumari P, Rajani DP, Pannecouque C, DeClercq E, Chikhalia KH, Future Med. Chem., 4, 1053 (2012)

[12] Zacharie B, Abbott SD, Bienvenu JF, Cameron AD, Cloutier J, Duceppe J, Ezzitouni A, Fortin D, Houde K, Lauzon C, Moreau N, Perron V, Wilb N, Asselin M, Doucet A, Fafard ME, Gaudreau D, Grouix B, Bournet FS, St- Amant N, Gagnon N, Gagnon L, Penney CL, J. Med. Chem., 53, 1138 (2010)

[13] Beijer FH, Kooijiman H, Spek AL, Sijbesma RP, Meijer EW, Angew. Chem.-Int. Edit., 37, 75 (1998)

[14] Pozharskii AF, Soldatenkov AT, Katritzky AR, Heterocycles in Life and Society, Wiley, Chichester, 1997.

[15] Smolin EM, Rapoport L, s-Triazines and Derivatives, Interscience, New York, 1959, pp. 217.268 (Chapter IV).

[16] Shie J, Fang J, J. Org. Chem., 72, 3141 (2007)

[17] Cheng T, Zhang D, Li H, Liu G, Green Chem., 16, 3401 (2014)

[18] Heitbaum M, Glorius F, Escher I, Angew. Chem.-Int. Edit., 45, 4732 (2006)

[19] Ngo H, Lin W, Top. Catal., 34, 85 (2005)

[20] Thomas JM, Raja R, Acc. Chem. Res., 41, 708 (2008)

[21] Abdollahi-Alibeik M, Rezaeipoor-Anari A, Catal. Sci. Technol., 4, 1151 (2014)

[22] Abdollahi-Alibeik M, Pouriayevali M, Catal. Commun., 22, 13 (2012)

[23] Chakraborty B, Viswanathan B, Catal. Today, 49(1-3), 253 (1999)

[24] Demel J, Cejka J, Stepnicka P, J. Mol. Catal. A-Chem., 274(1-2), 127 (2007)

[25] Juan JC, Zhang JC, Yarmo MA, J. Mol. Catal. A-Chem., 267(1-2), 265 (2007)

[26] Al-Hazmi MH, Apblett AW, Catal. Sci. Technol., 1, 621 (2011)

[27] Jiang CW, Zhong X, Luo ZH, RSC Adv., 4, 15216 (2014)

[28] Dong X, Hui Y, Xie X, Zhang P, Zhou G, Xie Z, RSC Adv., 3, 3222 (2013)

[29] Farzaneh F, Zamanifar E, Williams CD, J. Mol. Catal. A-Chem., 218(2), 203 (2004)

[30] Choi JS, Yoon SS, Jang SH, Ahn WS, Catal. Today, 111(3-4), 280 (2006)

[31] Wang LP, Kong AG, Chen B, Ding HM, Shan YK, He MY, J. Mol. Catal. A-Chem., 230(1-2), 143 (2005)

[32] Vetrivel S, Pandurangan A, J. Mol. Catal. A-Chem., 227(1-2), 269 (2005)

[33] Cortes Corberan V, Jia MJ, El-Haskouri J, Valenzuela RX, Beltran-Porter D, Amoros P, Catal. Today, 91, 127 (2004)

[34] Szegedi A, Popova M, Mavrodinova V, Urban M, Kiricsi I, Minchev C, Microporous Mesoporous Mater., 99, 149 (2007)

[35] Higashimoto S, Hu Y, Tsumura R, Iino K, Matsuoka M, Yamashita H, Shul YG, Che M, Anpo M, J. Catal., 235(2), 272 (2005)

[36] Abdollahi-Alibeika M, Moaddeli A, New J. Chem., 39, 2116 (2015)

[37] Shekouhy M, Khalafi-Nezhad A, Green Chem., 17, 4815 (2015)

[38] Zare A, Parhami A, Moosavi-Zare AR, Hasaninejad A, Khalafi-Nezhad A, Beyzavi MH, Can. J. Chem., 87, 416 (2009)

[39] Cooke G, Cremiers HA, Rotello VM, Tarbit B, Tetrahedron, 57, 2787 (2001)