Synthesis of perimidines using copper nitrate as an efficient catalyst

Synthesis and Reactivity in Inorganic, Metal-Organic and Nano-Metal Chemistry

Volumn 39, Issue 3, 2009, Pages 133-135

  Mobinikhaledi, Akbar ^a   Steel, Peter J ^b  

^a ARAK UNIVERSITY   (Iran)

^b UNIVERSITY OF CANTERBURY   (New Zealand)

Author keywords

Catalyst; Diaminonaphthalene; Perimidine

Indexed keywords

EID: 67651240594     PISSN: 15533174     EISSN: 15533182     Source Type: Journal    
DOI: 10.1080/15533170902784961     Document Type: Article

References (23)

1. Pozharskii, A.F., and Dalnikovskaya, V.V. Perimidines, Russ. Chem. Rev., 1981, 50, 816-835.
2. Deady, X. Bu, L.W., Finlay, G.J., Baguley, B.C., and Denny, W.A. Synthesis and cytotoxic activity of 7-oxo-7H-dibenz[f,ij] isoquinoline and 7-oxo-7H-benzo[e]perimidine derivatives. J. Med. Chem., 2001, 44, 2004-20014.
3. Undheim, K., and Benneche, T. Comprehensive Heterocyclic Chemistry, Katritzky, A.R. Ress, C. W, E.F.V. Scriven, Pergamon, Oxford, Vol. 6, 1996, pp. 93-231.
4. Starshikov, N.M., and Pozharskii, F.T. Synthesis of 2-(5-halogeno-2-f uryl)-2,3-dihydroperimidines Chemistry of Heterocyclic Compounds, 1975, 9, 922-924.
5. Morita, N., Dickstein, J.I., and Miller, S.I. Synthesis with ethynylphosphonium salts; nucleophilic additions to phenylethynyltriphenylphosphonium bromide. J. Chem. Soc. Perkin Trans., 1979, 1, 2103-2106.
6. Yavari, I., Jahani-moghaddam, F., Adib, F., and Bijanzadeh, H.R. Vinylphosphonium salt mediated simple synthesis of 7-oxo-7H-pyrido[1,2,3-cd] perimidine derivatives, dynamic NMR spectroscopic study of prototropic tautomerism in ethyl 1H-perimidine-2-carboxylate, Tetrahedron, 2002, 58, 6901-6906.
7. Hendrickson, J.B., and Hussoin, M.S. Seeking the ideal dehydrating reagent. J . Org. Chem., 1987, 52, 4137-4139.
8. Vanden Eynde, J.J., Delfosse, F., Mayence, A., and Haverbeke, Y.V. 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone, a mild catalyst for the formation of carbon-nitrogen bonds. Tetrahedron, 1995, 51, 5813-5818.
9. Mueller-Westerhoff, U.T., Vance, B., and Yoon, D.I. The synthesis of dithiolene dyes with strong near-IR absorption. Tetrahedron, 1991, 47, 909-932.
10. Deady, L.W., and Rodemann, T. Synthesis of perimidine and fused perimidine derivatives from reaction of 1,8-naphthalenediamine with an iminoisocoumarine. J. Heterocyclic. Chem., 1998, 35, 1417-1419.
11. Honda, K., Nakanishi, H., and Yabe, A. Reaction of 1,8-naphthalenediamine with dimethyl and diethyl acetylenedicarboxylates. Bull. Chem. Soc. Jpn., 1983, 56, 2338-2340.
12. Maquestiau, A., Berte, L., Mayence, A., and Vanden Eynd, J. An improved one-pot method for the preparation of 2-substituted 1H-perimidines, Synthetic Commun., 1991, 21, 2171-2180.
13. Popp, F.D., and Catala, A. Synthesis of potential antineoplastic agents. XI. Some 2-aryl-2,3-dihydro-1H-perimidines and a perimidine mustard. J. Heterocycicl. Chem., 1964, 1, 108-109.
14. Xianyong B., Junjie C., Leslie W.D., Clare L.S., Bruce C.B., Debra G., Shangjin Y., and William A.D. Synthesis and cytotoxic activity of N-[(alkylamino)alkyl]-carboxamide derivatives of 7-oxo-7H-benz[de]anthracene-7- oxo-7H-naphtho[1,2,3-de]quinoline, and 7-oxo-7Hbenzo[e]perimidine. Bioorg. Med. Chem., 2005, 13, 3657-3665.
15. Wiley, R.H., and Irick, G. 4-[N,N-Bis(2-halophenyl)amino)]benzaldehyde derivatives. J. Org. Chem., 1961, 26, 593-595.
16. Nasreen, A., Varala, R., and Adapa, R.S. Copper nitrate catalyzed efficient synthesis of bis(indolyl)methanes in acetonitrile at room temperature. J. Heterocycicl. Chem., 2007, 44, 983-987.
17. 2O. J. Heterocyclic. Chem., 2008, 45, 377-381.
18. 4 at room temperature under solvent free conditions. J. Iran. Chem. Soc., 2007, 4, 340-346.
19. Mobinikhaledi, A., Zendehdel, M., and Hasanvand Jamshidi, H. Zeolite-catalyzed synthesis of substituted benzimidazoles under solvent-free condition and microwave irradiation. Synthesis and Reactivity in Inorganic, Metal-Organic and nano-Metal Chemistry, 2007, 37, 175-177.
20. Mobinikhaledi, A., Foroughifar,N., G. Karimi., and Foroughifar, N. Onepot synthesis of tetrahydropyrimidines catalyzed by zeolite. Synthesis and Reactivity in Inorganic, Metal-Organic and nano-Metal Chemistry, 2007, 37, 279-282.
21. Zendehdel, M., Mobinikhaledi, A., and Asgari, A. Zeolite an efficient catalyst for the Biginelli condensation reaction. J Incl Phenom Macrocycl Chem., 2008, 60, 353-357.
22. Mobinikhaledi, A., Foroughifar, N., and Goli, R. Synthesis of some benzotriazole-substituted perimidines. Phosphorus, Sulfur, and Silicon and the related Elements, 2005, 180, 2549-2554.
23. Mobinikhaledi, A., Amrollahi, M.A., Foroughifar, N., and Fathinejad Jirandehi, H. Microwave assisted synthesis of some 2-alkyl- and 2-arylperimidines. Asian J of Chem., 2005, 17, 2411-2414.