A rapid and high efficient microwave promoted multicomponent domino reaction for the synthesis of spirooxindole derivatives

Ramin Ghahremanzadeh; Zahra Rashid; Amir-Hassan Zarnani; Hossein Naeimi

Journal of Industrial and Engineering Chemistry, Vol.20, No.6, 4076-4084, November, 2014

DOI10.1016/j.jiec.2013.12.109 Export Citation

A rapid and high efficient microwave promoted multicomponent domino reaction for the synthesis of spirooxindole derivatives

Ramin Ghahremanzadeh, Zahra Rashid¹, Amir-Hassan Zarnani², and Hossein Naeimi^{1, †}

Nanobiotechnology Research Center, Avicenna Research Institute, ACECR, Tehran, Islamic Republic of Iran
¹Department of Organic Chemistry, Faculty of Chemistry, University of Kashan, Kashan 87317, Islamic Republic of Iran
²Reproductive Immunology Research Center, Avicenna Research Institute, ACECR, Tehran, Islamic Republic of Iran

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A simple, efficient and rapid method has been developed for synthesis of 6,6-dimethyl-4-phenyl-6,7-dihydro-1H-spiro[furo[3,4-b]quinoline-9,3'-indoline]1,2',8(3H,4H,5H)-trione derivatives. These heterocycles were prepared through domino one-pot and multicomponent condensation reactions of isatins, dimedone, and anilinolactones in the presence of alum (15 mol%) as an inexpensive, nontoxic, convenient, and available Lewis acid catalyst under microwave irradiation. The corresponding products have been obtained in excellent isolated yields between 78% and 90%, with high purity, in short reaction times about 10-12 min and easy work up.

Keywords:Multi-component reaction;Alum [KAl(SO4)2·12H2O];Alum [KAl(SO4)2·12H2O];Microwave;Anilinolactone;Spirooxindole

[References]

Yang Y, Gao M, Wu L, Deng C, Zhang D, Gao Y, Zhu Y, Wu Y, Tetrahedron, 67, 5142 (2011)
Zhang L, Sun J, Yan C, Tetrahedron Lett., 53, 6965 (2012)
Fu L, Shi Q, Shi Y, Jiang B, Tu S, ACS Comb. Sci., 15, 135 (2013)
Herrera M, Knepper I, Souza N, Villinger A, Sosnovskikh V, Iaroshenko V, ACS Comb. Sci., 14, 434 (2012)
Xiao Z, Lei M, Hu L, Tetrahedron Lett., 52, 7099 (2011)
Jiang B, Xue L, Wang X, Tu M, Liu Y, Tu S, Tetrahedron Lett., 53, 1261 (2012)
Chaudhary S, Harding W, Tetrahedron, 67, 569 (2011)
Mohan S, Kumar B, Dinda S, Naik D, Seenivasan SP, Kumar V, Rana D, Brahmkshatriy P, Bioorg. Med. Chem. Lett., 22, 7539 (2012)
dela Hoz A, Diaz-Ortiz A, Moreno A, Chem. Soc. Rev., 34, 164 (2005)
Dolzhenko A, Kalinina S, Kalinin D, Rsc Adv., 3, 15853 (2013)
Baeza A, Najera C, Retamosa MG, Sansano JM, Synthesis, 2787 (2005)
Antonchick AP, Gerding-Reimers C, Catarinella M, Schurmann M, Preut H, Ziegler S, Rauh D, Waldmann H, Nat. Chem., 2, 735 (2010)
Popp FD, J. Heterocycl. Chem., 21, 1367 (1984)
Pajouhesh H, Parsons R, Popp FD, J. Pharm. Sci., 72, 318 (1983)
Garrido F, Ibanez J, Gonalons E, Giraldez A, Eur. J. Med. Chem., 10, 143 (1975)
Yong SR, Ung AT, Pyne SG, Skelton BW, White AH, Tetrahedron, 63, 5579 (2007)
Abdel-Rahman AH, Keshk EM, Hanna MA, El-Bady SM, J. Med. Chem., 12, 2483 (2004)
Okita T, Isobe M, Tetrahedron, 50, 11143 (1994)
Rosenmond P, Hosseini-Merescht M, Bub C, Liebigs Ann. Chem., 2, 151 (1994)
Usui T, Kondoh M, Cui CB, Mayumi T, Osada H, Biochem. J., 333, 543 (1998)
Cui CB, Kakeya H, Osada H, J. Antibiot., 49, 832 (1996)
Alizadeh A, Rezvanian A, Zhu LG, J. Org. Chem., 77, 4385 (2012)
Rao BM, Reddy GN, Reddy TV, Devi BLAP, Prasad RBN, Yadav JS, Reddy BVS, Tetrahedron Lett., 54, 2466 (2013)
Chai SJ, Lai YF, Xu JC, Zheng H, Zhu Q, Zhang PF, Adv. Synth. Catal., 353, 371 (2011)
Rad-Moghadam K, Youseftabar-Miri L, Synlett, 13, 1969 (2010)
Tisseh ZN, Ahmadi F, Dabiri M, Khavasi HR, Bazgir A, Tetrahedron Lett., 53, 3603 (2012)
Wang L, Jiao N, Qiu J, Yu J, Liu J, Guo F, Liu Y, Tetrahedron, 66, 339 (2010)
Paul S, Das A, Tetrahedron Lett., 54, 1149 (2013)
El-Assaly SA, Pharm. Chem., 3, 81 (2011)
Ahadi S, Ghahremanzadeh R, Mirzaei P, Bazgir A, Tetrahedron, 65, 9316 (2009)
Ghahremanzadeh R, Fereshtehnejad F, Yassaee Z, Amanpour T, Bazgir A, J. Histochem. Cytochem., 47, 967 (2010)
Ghahremanzadeh R, Shakibaei GI, Ahadi S, Bazgir A, J. Comb. Chem., 12, 194 (2010)
Ghahremanzadeh R, Rashid Z, Zarnani AH, Naeimi H, Appl. Catal. A: Gen., 467, 270 (2013)
Cheng C, Jiang B, Tu SJ, Li G, Green Chem., 13, 210 (2011)
Wang SL, Cheng C, Wu FY, Jiang B, Shi F, Tu S, Rajale T, Li G, Tetrahedron, 67, 4485 (2011)
Wang S, Cheng C, Gong F, Wu F, Jiang B, Zhou J, Tu S, Chin. J. Chem., 29, 2101 (2011)
Hitotsuyanagi Y, Kobayashi M, Fukuyo M, Takeya K, Itokawa H, Tetrahedron Lett., 38, 8295 (1997)
Chen H, Shi D, J. Comb. Chem., 12, 571 (2010)
Verma GK, Raghuvanshi K, Kumar R, Singh SM, Tetrahedron Lett., 53, 399 (2012)
Shi CL, Shi DQ, Kim SH, Huang ZB, Ji SJ, Ji M, Tetrahedron, 64, 2425 (2008)
Rad-Moghadam K, Youseftabar-Miri L, Synlett, 13, 1969 (2010)
Nandi GS, Samai S, Singh MS, Synlett, 7, 1133 (2010)

[Referenced By]

[1] Yang Y, Gao M, Wu L, Deng C, Zhang D, Gao Y, Zhu Y, Wu Y, Tetrahedron, 67, 5142 (2011)

[2] Zhang L, Sun J, Yan C, Tetrahedron Lett., 53, 6965 (2012)

[3] Fu L, Shi Q, Shi Y, Jiang B, Tu S, ACS Comb. Sci., 15, 135 (2013)

[4] Herrera M, Knepper I, Souza N, Villinger A, Sosnovskikh V, Iaroshenko V, ACS Comb. Sci., 14, 434 (2012)

[5] Xiao Z, Lei M, Hu L, Tetrahedron Lett., 52, 7099 (2011)

[6] Jiang B, Xue L, Wang X, Tu M, Liu Y, Tu S, Tetrahedron Lett., 53, 1261 (2012)

[7] Chaudhary S, Harding W, Tetrahedron, 67, 569 (2011)

[8] Mohan S, Kumar B, Dinda S, Naik D, Seenivasan SP, Kumar V, Rana D, Brahmkshatriy P, Bioorg. Med. Chem. Lett., 22, 7539 (2012)

[9] dela Hoz A, Diaz-Ortiz A, Moreno A, Chem. Soc. Rev., 34, 164 (2005)

[10] Dolzhenko A, Kalinina S, Kalinin D, Rsc Adv., 3, 15853 (2013)

[11] Baeza A, Najera C, Retamosa MG, Sansano JM, Synthesis, 2787 (2005)

[12] Antonchick AP, Gerding-Reimers C, Catarinella M, Schurmann M, Preut H, Ziegler S, Rauh D, Waldmann H, Nat. Chem., 2, 735 (2010)

[13] Popp FD, J. Heterocycl. Chem., 21, 1367 (1984)

[14] Pajouhesh H, Parsons R, Popp FD, J. Pharm. Sci., 72, 318 (1983)

[15] Garrido F, Ibanez J, Gonalons E, Giraldez A, Eur. J. Med. Chem., 10, 143 (1975)

[16] Yong SR, Ung AT, Pyne SG, Skelton BW, White AH, Tetrahedron, 63, 5579 (2007)

[17] Abdel-Rahman AH, Keshk EM, Hanna MA, El-Bady SM, J. Med. Chem., 12, 2483 (2004)

[18] Okita T, Isobe M, Tetrahedron, 50, 11143 (1994)

[19] Rosenmond P, Hosseini-Merescht M, Bub C, Liebigs Ann. Chem., 2, 151 (1994)

[20] Usui T, Kondoh M, Cui CB, Mayumi T, Osada H, Biochem. J., 333, 543 (1998)

[21] Cui CB, Kakeya H, Osada H, J. Antibiot., 49, 832 (1996)

[22] Alizadeh A, Rezvanian A, Zhu LG, J. Org. Chem., 77, 4385 (2012)

[23] Rao BM, Reddy GN, Reddy TV, Devi BLAP, Prasad RBN, Yadav JS, Reddy BVS, Tetrahedron Lett., 54, 2466 (2013)

[24] Chai SJ, Lai YF, Xu JC, Zheng H, Zhu Q, Zhang PF, Adv. Synth. Catal., 353, 371 (2011)

[25] Rad-Moghadam K, Youseftabar-Miri L, Synlett, 13, 1969 (2010)

[26] Tisseh ZN, Ahmadi F, Dabiri M, Khavasi HR, Bazgir A, Tetrahedron Lett., 53, 3603 (2012)

[27] Wang L, Jiao N, Qiu J, Yu J, Liu J, Guo F, Liu Y, Tetrahedron, 66, 339 (2010)

[28] Paul S, Das A, Tetrahedron Lett., 54, 1149 (2013)

[29] El-Assaly SA, Pharm. Chem., 3, 81 (2011)

[30] Ahadi S, Ghahremanzadeh R, Mirzaei P, Bazgir A, Tetrahedron, 65, 9316 (2009)

[31] Ghahremanzadeh R, Fereshtehnejad F, Yassaee Z, Amanpour T, Bazgir A, J. Histochem. Cytochem., 47, 967 (2010)

[32] Ghahremanzadeh R, Shakibaei GI, Ahadi S, Bazgir A, J. Comb. Chem., 12, 194 (2010)

[33] Ghahremanzadeh R, Rashid Z, Zarnani AH, Naeimi H, Appl. Catal. A: Gen., 467, 270 (2013)

[34] Cheng C, Jiang B, Tu SJ, Li G, Green Chem., 13, 210 (2011)

[35] Wang SL, Cheng C, Wu FY, Jiang B, Shi F, Tu S, Rajale T, Li G, Tetrahedron, 67, 4485 (2011)

[36] Wang S, Cheng C, Gong F, Wu F, Jiang B, Zhou J, Tu S, Chin. J. Chem., 29, 2101 (2011)

[37] Hitotsuyanagi Y, Kobayashi M, Fukuyo M, Takeya K, Itokawa H, Tetrahedron Lett., 38, 8295 (1997)

[38] Chen H, Shi D, J. Comb. Chem., 12, 571 (2010)

[39] Verma GK, Raghuvanshi K, Kumar R, Singh SM, Tetrahedron Lett., 53, 399 (2012)

[40] Shi CL, Shi DQ, Kim SH, Huang ZB, Ji SJ, Ji M, Tetrahedron, 64, 2425 (2008)

[41] Rad-Moghadam K, Youseftabar-Miri L, Synlett, 13, 1969 (2010)

[42] Nandi GS, Samai S, Singh MS, Synlett, 7, 1133 (2010)