Sulfamic acid: A green and efficient catalyst for synthesis of mono-, bis-, and spiro- perimidines
الموضوعات : Iranian Journal of Catalysis
Mohamad Ali Bodaghifard
1
(Department of Chemistry, Faculty of Science, Arak University, 38156-88138, Arak, Iran.)
Najmieh Ahadi
2
(Department of Chemistry, Faculty of Science, Arak University, 38156-88138, Arak, Iran.)
الکلمات المفتاحية: Green synthesis, Catalyst, Sulfamic acid, Perimidine, Spiroperimidine,
ملخص المقالة :
Mild and applicable synthesis of mono-, bis-, and spiro- perimidines is demonstrated in high yields via the condensation of 1,8-diaminonaphthalene and aldehydes or ketones in the presence of sulfamic acid as a green and highly efficient catalyst. This environmentally benign and clean synthetic pathway offers several advantages, such as high yields, short reaction times and easy work-up procedure.
[1] (a) K. Undheim, T. Benneche, A.R. Katritzky, C.W. Rees, E.F.V. Scriven (Eds.), Comprehensive Heterocyclic Chemistry, vol. 6, Pergamon, Oxford, 1984, p. 93. (b) I.A.S. Smellie, A. Fromm, S.A. Moggach, R.M. Paton, Carbohydr. Res. 346 (2011) 43–49.
[2] A.F. Pozharskii, V.V. Dalnikovskaya, Perimidines, Russ. Chem. Rev. 50 (1981) 816–835.
[3] X. Bu, L.W. Deady, G.J. Finlay, B.C. Baguley, W.A. Denny, J. Med. Chem. 44 (2001) 2004–2014.
[4] J.M. Herbert, P.D. Woodgate, W.A. Denny, J. Med. Chem. 30 (1987) 2081–2086.
[5] K. Arya, A. Dandia, Lett. Org. Chem. 4 (2007) 378–383.
[6] M. Dzieduszycka, S. Martelli, M. Arciemiuk, M.M. Bontemps-Gracz, A. Kupiec, E. Borowski, Bioorg. Med. Chem. 10 (2002) 1025–1035.
[7] (a) W.D. Ramsden, L.F. Valente, L.S. Bernard, US Patent 6348592 (2002). (b) I. Koca, S.H. Ungoren, I.E. Kıbrız, Dyes Pigments 95 (2012) 421-426
[8] R.F. Malherbe, US Patent (1983) 4389321.
[9] (a) R. Davis, N. Tamaoki, Org. Lett. 7 (2005) 1461-1464. (b) R. Davis, N. Tamaoki, Chem. Eur. J. 13 (2007) 626-631.
[10] (a) P. Bazinet, T.-G. Ong, J.S. O’Brien, N. Lavoie, E. Bell, G.P.A. Yap, I. Korobkov, D.S. Richeson, Organometallics 26 (2007) 2885–2895. (b) B. Alici, I. Ozdemir, K. Karaaslan, E. Çetinkaya, B.J. Cetinkaya, J. Mol. Catal. A: Chem. 231 (2005) 261–264.
[11] J. Zhang, S. Zhang, Synth. Commun. 37 (2007) 2615-2624.
[12] A. Mobinikhaledi, P.J. Steel, Synth. React. Inorg. Met. Org. Chem. 39 (2009) 133–135.
[13] A. Mobinikhaledi, N. Foroughifar, N. Basaki, Turk. J. Chem. 33 (2009) 555-560.
[14] J. Zhang, S.L. Zhang, J.M. Zhang, Chin. Chem. Lett. 18 (2007) 1057–1060.
[15] H. Alinezhad, M. Zare, J. Chil. Chem. Soc. 58 (2013) 1840-1841.
[16] S.L. Zhang, J.M. Zhang, Chin. J. Chem. 26 (2008) 185-189.
[17] Z. Yasaei, P. Mirzaei, A. Bazgir, C. R. Chim. 13 (2010) 1308–1312.
[18] G.K.S. Prakash, F. Paknia, A. Narayan, T. Mathew, G.A. Olah, J. Fluorine Chem. 152 (2013) 99–105.
[19] P.R. Singh, D.U. Singh, Sh.D. Samant, Synlett (2004) 1909–1912.
[20] J.S. Yadav, P.P. Rao, D. Sreenu, R.S. Rao, V. Kumar, K. Nagaiah, A.R. Prasad, Tetrahedron Lett. 46 (2005) 7249–7253.
[21] D.J. Upadhyaya, A. Barge, R. Stefania, G. Cravotto, Tetrahedron Lett. 48 (2007) 8318–8322.
[22] A. Heydari, S. Khaksar, M. Pourayoubi, A.R. Mahjoub, Tetrahedron Lett. 48 (2007) 4059–4060.
[23] S.B. Patil, P.R. Singh, M.P. Surpur, S.D. Samant, Ultrason. Sonochem. 14 (2007) 515–518.
[24] M.M. Heravi, L. Ranjbar, F. Derikvand, F.F. Bamoharram, J. Mol. Catal. A: Chem. 276 (2007) 226-229.
[25] H.R. Darabi, Sh. Mohandessi, K. Aghapoor, F. Mohsenzadeh, Catal. Commun. 8 (2007) 389-392.
[26] A. Kamal, B.R. Prasad, A.M. Reddy, M.N. Khan, Catal. Commun. 8 (2007) 1876–1880.
[27] N. Foroughifar, A. Mobinikhaledi, M.A. Bodaghifard, H. Moghanian, S. Ebrahimi, Synth. React. Inorg. Met. Org. Chem. 39 (2009) 161–164.
[28] H. Zeng, H. Li, H. Shao, Ultrason. Sonochem. 16 (2009) 758-762.
[29] M.G. Montes D’Oca, R.M. Soares, R. R. de Moura, G. V. de Freitas, Fuel 97 (2012) 884-886.
[30] M. Kidwai, R. Chauhan, RSC Adv. 2 (2012) 7660-7665.
[31] P.G. Hegadea, M.M. Manea, J.D. Patil, M.D. Pore, Synth. Commun. 44 (2014) 3384-3391.
[32] M.A. Bodaghifard, M. Solimannejad, S. Asadbegi, S. Dolatabadifarahani, Res. Chem. Intermed. 42 (2016) 1165-1179.
[33] O. Maloshitskaya, J. Sinkkonen, V.V. Ovcharenko, K.N. Zelenin and K. Pihlaja, Tetrahedron 60 (2004) 6913-6921.
[34] A. Mobinikhaledi, H. Moghanian, F. Sasani, Int. J. Green Nanotech. Phys. Chem. 2 (2010) 47-52.
[35] M. Azam, I. Warad, S.I. Al-Resayes, N. Alzaqri, M.R. Khan, R. Pallepogu, S. Dwivedi, J. Musarrat, M. Shakir, J. Mol. Struct. 1047 (2013) 48-54.
[36] N.M. Starshikov, A.F. Pozharskii, Chem. Heterocycl. Compd. 16 (1980) 81-85.
