How to cite this paper
Zonouz, A., Moghani, D & Okhravi, S. (2014). A facile and efficient protocol for the synthesis of 2-amino-3-cyano-4H-pyran derivatives at ambient temperature.Current Chemistry Letters, 3(2), 71-74.
Refrences
[1] Zamocka J., Misikova E., Durinda J. (1991) Preparation, structural determination and activity of some 5-hydroxy-4-oxo-[4H-pyrano(2-yl)methyl]-2-alkoxycarbanilates. Pharmazie, 46, 610-613.
[2] Witte E. C., Neubert P., Roesch, A. (1986) 7-(piperazinyl propoxy)-2H-1-benzopyran-2-ones. Ger. Offen. DE3427985.
[3] Wang J. L., Liu D., Zhang Z. J., Shan S., Han X., Srinivasula S. M., Croce C. M., Alnemri E. S., Huang Z (2000) Structure-based discovery of an organic compound that binds Bcl-2 protein and induces apoptosis of tumor cells. Proc Natl Acad Sci U.S.A. 97(13): 7124-29.
[4] El-Saghier A. M. M., Naili M. B., Rammash B. Kh., Saleh N. A., Kreddan K. M. (2007) Synthesis and antibacterial activity of some new fused chromenes. Arkivoc xvi, 83-91.
[5] Kumar R. R., Perumal S., Senthilkumar P., Yogeeswari P., Sriram D. (2007) An atom efficient, solvent-free, green synthesis and antimycobacterial evaluation of 2-amino-6-methyl-4-aryl-8-[(E)-arylmethylidene]-5,6,7,8-tetrahydro-4H-pyrano[3,2-c]pyridine-3-carbonitriles. Bioorg. Med. Chem. Lett. 17, 6459-6462.
[6] Fairlamb I. J. S., Marrison L. R., Dickinson J. M., Lu F.-J., Schmidt J. P. (2004) 2-Pyrones possessing antimicrobial and cytotoxic activities. Bioorg. Med. Chem., 12, 4285-4299.
[7] Aytemir M. D., Erol D. D., Hider R. C., ?zalp M. (2003) Synthesis and Evaluation of Antimicrobial Activity of New 3-Hydroxy-6-methyl-4-oxo-4H-pyran-2-carboxamide derivatives. Turk. J. Chem., 27, 757-764.
[8] Kidwai M., Saxena S., Khan M. K. R., Thukral S.S. (2005) Aqua mediated synthesis of substituted 2-amino-4H-chromenes and in vitro study as antibacterial agents. Bioorg. Med. Chem. Lett., 15, 4295-4298.
[9] Nicolaou K. C., Pfefferkorn J. A., Cao G. Q. (2000) Selenium-based solid-phase synthesis of benzopyrans I: applications to combinatorial synthesis of natural products. Angew. Chem., 39,734-739.
[10] Hafez E. A., Elnagdi M. H., Elagamey A. A., El-Taweel F. A. (1987) Nitriles in Heterocyclic Synthesis: Novel synthesis of benzo[c]coumarin and of benzo[c]pyrano[3,2-c]quinoline derivatives. Heterocycles, 26, 903.
[11] Kuthan J. (1983) Pyrans, thiopyrans, and selenopyrans. Adv. Heterocycl. Chem., 34, 145-303.
[12] Hatakeyama S., Ochi N., Numata H., Takano S. (1988) A new route to substituted 3-methoxycarbonyldihydropyrans; enantioselective synthesis of (–)-methyl elenolate. J. Chem. Soc. Chem. Commun., 17, 1202-1204.
[13] Suarez M, Salfran E, Verdecia Y, Ochoa E, Alba L, Martin N, Martinez R, Quinteiro M, Seoane C, Novoa H, Blaton N, Peeters O M, De Ranter C (2002) X-Ray and theoretical structural study of novel 5,6,7,8-tetrahydrobenzo-4H-pyrans. Tetrahedron, 58, 953-960.
[14] Martin N., Pascual C., Seoane C., Soto J. L. (1987) The use of some activated nitriles in heterocyclic syntheses. Heterocycles, 26, 2811-2816.
[15] Harb A. F., Hesien A. M., Metwally S. A., Elnagdi M. H. (1989) The reaction of ethyl 6-amino-5-cyano-4-aryl-2-methyl-4H-pyran-3-carboxylate with nucleophilic reagents. Liebigs Ann. Chem., 585-588.
[16] Zayed S. E., Abou Elmaged E. I., Metwally S. A., Elnagdi M. H. (1991) Reactions of six-membered heterocyclic B-enaminonitriles with electrophilic reagents. Collect. Czech. Chem. Commun., 56, 2175-2182.
[17] Elnagdi M. H., Adbel-Motaleb R. M., Mustafa M. (1987) Studies on heterocyclic enamines: New syntheses of 4H-pyranes, pyranopyrazoles and pyranopyrimidines. J. Heterocycl. Chem., 24, 1677-1681.
[18] Seshu Babu N., Pasha N., Venkateswara Roa K. T., Sai Prasad P. S., Lingaiah N. (2008) A heterogeneous strong basic Mg/La mixed oxide catalyst for efficient synthesis of polyfunctionalized pyrans. Tet. Lett., 49, 2730-2733.
[19] Kumar D., Reddy V. B., Mishra B. G., Rana R. K., Nadagouda M. N., Varma R.S. (2007) Nanosized magnesium oxide as catalyst for the rapid and green synthesis of substituted 2-amino-2-chromenes. Tetrahedron, 63, 3093-3097.
[20] Kumar D., Reddy V. B., Sharad Sh., Dube U., Kapur S. (2009) A facile one-pot green synthesis and antibacterial activity of 2-amino-4H-pyrans and 2-amino-5-oxo-5,6,7,8-tetrahydro-4H-chromenes. Eur. J. Med. Chem., 44, 3805-3809.
[21] Moshtaghi Z. A., Eskandari I., Moghani, D. (2012) Acceleration of multicomponent reactions in aqueous medium: multicomponent synthesis of a 4H-pyran library. Chem. Sci. Trans., 1, 91-102.
[22] Moshtaghi Z. A., Eskandari I., Khavasi H. R. (2012) A green and convenient approach for the synthesis of methyl 6-amino-5-cyano-4-aryl-2,4-dihydropyrano[2,3-c]pyrazole-3-carboxylates via a one-pot, multi-component reaction in water. Tetrahedron Lett., 53, 5519-5522.
[2] Witte E. C., Neubert P., Roesch, A. (1986) 7-(piperazinyl propoxy)-2H-1-benzopyran-2-ones. Ger. Offen. DE3427985.
[3] Wang J. L., Liu D., Zhang Z. J., Shan S., Han X., Srinivasula S. M., Croce C. M., Alnemri E. S., Huang Z (2000) Structure-based discovery of an organic compound that binds Bcl-2 protein and induces apoptosis of tumor cells. Proc Natl Acad Sci U.S.A. 97(13): 7124-29.
[4] El-Saghier A. M. M., Naili M. B., Rammash B. Kh., Saleh N. A., Kreddan K. M. (2007) Synthesis and antibacterial activity of some new fused chromenes. Arkivoc xvi, 83-91.
[5] Kumar R. R., Perumal S., Senthilkumar P., Yogeeswari P., Sriram D. (2007) An atom efficient, solvent-free, green synthesis and antimycobacterial evaluation of 2-amino-6-methyl-4-aryl-8-[(E)-arylmethylidene]-5,6,7,8-tetrahydro-4H-pyrano[3,2-c]pyridine-3-carbonitriles. Bioorg. Med. Chem. Lett. 17, 6459-6462.
[6] Fairlamb I. J. S., Marrison L. R., Dickinson J. M., Lu F.-J., Schmidt J. P. (2004) 2-Pyrones possessing antimicrobial and cytotoxic activities. Bioorg. Med. Chem., 12, 4285-4299.
[7] Aytemir M. D., Erol D. D., Hider R. C., ?zalp M. (2003) Synthesis and Evaluation of Antimicrobial Activity of New 3-Hydroxy-6-methyl-4-oxo-4H-pyran-2-carboxamide derivatives. Turk. J. Chem., 27, 757-764.
[8] Kidwai M., Saxena S., Khan M. K. R., Thukral S.S. (2005) Aqua mediated synthesis of substituted 2-amino-4H-chromenes and in vitro study as antibacterial agents. Bioorg. Med. Chem. Lett., 15, 4295-4298.
[9] Nicolaou K. C., Pfefferkorn J. A., Cao G. Q. (2000) Selenium-based solid-phase synthesis of benzopyrans I: applications to combinatorial synthesis of natural products. Angew. Chem., 39,734-739.
[10] Hafez E. A., Elnagdi M. H., Elagamey A. A., El-Taweel F. A. (1987) Nitriles in Heterocyclic Synthesis: Novel synthesis of benzo[c]coumarin and of benzo[c]pyrano[3,2-c]quinoline derivatives. Heterocycles, 26, 903.
[11] Kuthan J. (1983) Pyrans, thiopyrans, and selenopyrans. Adv. Heterocycl. Chem., 34, 145-303.
[12] Hatakeyama S., Ochi N., Numata H., Takano S. (1988) A new route to substituted 3-methoxycarbonyldihydropyrans; enantioselective synthesis of (–)-methyl elenolate. J. Chem. Soc. Chem. Commun., 17, 1202-1204.
[13] Suarez M, Salfran E, Verdecia Y, Ochoa E, Alba L, Martin N, Martinez R, Quinteiro M, Seoane C, Novoa H, Blaton N, Peeters O M, De Ranter C (2002) X-Ray and theoretical structural study of novel 5,6,7,8-tetrahydrobenzo-4H-pyrans. Tetrahedron, 58, 953-960.
[14] Martin N., Pascual C., Seoane C., Soto J. L. (1987) The use of some activated nitriles in heterocyclic syntheses. Heterocycles, 26, 2811-2816.
[15] Harb A. F., Hesien A. M., Metwally S. A., Elnagdi M. H. (1989) The reaction of ethyl 6-amino-5-cyano-4-aryl-2-methyl-4H-pyran-3-carboxylate with nucleophilic reagents. Liebigs Ann. Chem., 585-588.
[16] Zayed S. E., Abou Elmaged E. I., Metwally S. A., Elnagdi M. H. (1991) Reactions of six-membered heterocyclic B-enaminonitriles with electrophilic reagents. Collect. Czech. Chem. Commun., 56, 2175-2182.
[17] Elnagdi M. H., Adbel-Motaleb R. M., Mustafa M. (1987) Studies on heterocyclic enamines: New syntheses of 4H-pyranes, pyranopyrazoles and pyranopyrimidines. J. Heterocycl. Chem., 24, 1677-1681.
[18] Seshu Babu N., Pasha N., Venkateswara Roa K. T., Sai Prasad P. S., Lingaiah N. (2008) A heterogeneous strong basic Mg/La mixed oxide catalyst for efficient synthesis of polyfunctionalized pyrans. Tet. Lett., 49, 2730-2733.
[19] Kumar D., Reddy V. B., Mishra B. G., Rana R. K., Nadagouda M. N., Varma R.S. (2007) Nanosized magnesium oxide as catalyst for the rapid and green synthesis of substituted 2-amino-2-chromenes. Tetrahedron, 63, 3093-3097.
[20] Kumar D., Reddy V. B., Sharad Sh., Dube U., Kapur S. (2009) A facile one-pot green synthesis and antibacterial activity of 2-amino-4H-pyrans and 2-amino-5-oxo-5,6,7,8-tetrahydro-4H-chromenes. Eur. J. Med. Chem., 44, 3805-3809.
[21] Moshtaghi Z. A., Eskandari I., Moghani, D. (2012) Acceleration of multicomponent reactions in aqueous medium: multicomponent synthesis of a 4H-pyran library. Chem. Sci. Trans., 1, 91-102.
[22] Moshtaghi Z. A., Eskandari I., Khavasi H. R. (2012) A green and convenient approach for the synthesis of methyl 6-amino-5-cyano-4-aryl-2,4-dihydropyrano[2,3-c]pyrazole-3-carboxylates via a one-pot, multi-component reaction in water. Tetrahedron Lett., 53, 5519-5522.