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Green Synthesis, Cyclization and Biological Study of Novel Series of 1,8-Naphthyridines Using Friedlander Condensation
Asian Journal of Chemistry,
Vol. 30 No. 8 (2018): Vol 30 Issue 8
Abstract
A novel and green synthesis of 1,8-naphthyridines like 2,2,2-trifluoro-1-(2-methyl-1,8-naphthyridin- 3-yl)ethanone, 2,2,2-trifluoro-1-(2-phenyl-1,8-naphthyridin-3-yl)ethanone, 2-trifluoro-1-(2-phenyl-1,8-naphthyridin-3-yl)ethanone, 1-(2-(4-chlorophenyl)-1,8-naphthyridine-3-yl)-2,2,2-trifluoroethanone, 2,2,2-trifluoro-1-(2-(furan-2-yl)-1,8-naphthyridin-3-yl)ethanone and 2,2,2-trifluoro-1-(2-(thiophen-2-yl)-1,8-naphthyridin-3-yl)ethanone from ecofriendly and inexpensive NaH catalyzed Friedlander condensation of 2-aminonicotinaldehyde (1) through carbonyl complexes containing a-methylene moiety (2) has been achieved in eco-friendly by microwave irradiation. Elemental analysis, TLC, IR, 1H NMR, 13C NMR and GC-Mass spectroscopy were analyzed the compounds character. The final compounds were tested antimicrobial culture study. In the antibacterial and antifungal study the compounds 3d and 3e shows very good activity against Escherichia coli, Pseudomonas aeruginosa and Staphylococcus aureus and 3b, 3c, 3d, 3e and 3f shows good action against Penicillium species, Candida albicans and Aspergillus niger, compare to 3a. In this article, a very simple and low-cost method is described for the production of a novel sequence of 1,8-naphthyridines complex and provide very good microbial activity.
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- B.L. Hayes, Aldrichimica Acta, 37, 66 (2004).
- B.M. Sahoo, J. Appl. Pharm., 8, e106 (2016); https://doi.org/10.4172/1920-4159.1000e106.
- V. Polshettiwar, M.N. Nadagouda and R.S. Varma, Aust. J. Chem., 62, 16 (2009); https://doi.org/10.1071/CH08404
- C.O. Kappe, Chimia, 60, 308 (2006); https://doi.org/10.2533/000942906777836273.
- P. Lidström, J. Tierney, B. Wathey and J. Westman, Tetrahedron, 57, 9225 (2001); https://doi.org/10.1016/S0040-4020(01)00906-1.
- P. Acosta, E. Butassi, B. Insuasty, A. Ortiz, R. Abonia, S. Zacchino and J. Quiroga, Molecules, 20, 8499 (2015); https://doi.org/10.3390/molecules20058499.
- B. Ondruschka, and W. Bonrath, Chimia, 60, 326 (2006); https://doi.org/10.2533/000942906777836246.
- S. Caddick, Tetrahedron, 51, 10403 (1995); https://doi.org/10.1016/0040-4020(95)00662-R.
- R.S. Varma, Green Chem., 1, 43 (1999); https://doi.org/10.1039/a808223e.
- P. Lidstrom, J. Tierney, B. Wathey and J. Westman, Tetrahedron, 57, 9225 (2001); https://doi.org/10.1016/S0040-4020(01)00906-1.
- J.T. Leonard, R. Gangadhar, S.K. Gnanasam, S. Ramachandran, M. Saravanan and S.K. Sridhar, Biol. Pharm. Bull., 25, 798 (2002).
- I.P. Singh, S. Kumar and S. Gupta, Med. Chem., 13, 430 (2017); https://doi.org/10.2174/1573406412666161228112127.
- R.A. Mekheimer, A.M. Abdel Hameed and K.U. Sadek, ARKIVOC, 269 (2007); https://doi.org/10.3998/ark.5550190.0008.d30.
- K. Mogilaiah, G. Ramasudhakar and N.V. Reddy, Indian J. Chem., 42B, 1753 (2003).
- D. Ramesh, M.T. Chary, E. Laxminarayana and B. Sreenivasuli, Indian J. Chem., 49B, 1271 (2010).
- T.R. Ravikumar Naik, H.S. Bhojya Naik, M. Raghavendra and S. G.K. Naik, ARKIVOC, 15, 84 (2006); https://doi.org/10.3998/ark.5550190.0007.f11.
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- S. Abu-Melha, Acta Chim. Slov., 64, 919 (2017); https://doi.org/10.17344/acsi.2017.3617.
- R. Álvarez-Manzo, J. Mendoza-Canales, S. Castillo-Cervantes and J. Marín-Cruz, J. Mex. Chem. Soc., 57, 30 (2013); https://doi.org/10.29356/jmcs.v57i1.234.
- E.B. Jahromi and A. Mehranpour, J. Hetrocycl. Chem., 54, 1210 (2017); https://doi.org/10.1002/jhet.2694.
- A. Madaan, R. Verma, V. Kumar, A.T. Singh, S.K. Jain and M. Jaggi, Arch. Pharm., 348, 837 (2015); https://doi.org/10.1002/ardp.201500237.
- S.M. Behalo and G. Mele, J. Hetrocycl. Chem., 54, 295 (2017); https://doi.org/10.1002/jhet.2581.
- R. Rajkumar, K. Saravanamani and S.P. Rajendran, J. Chem. Pharm. Sci., 10, 307 (2017).
- A. Corsaro, U. Chiacchio, V. Pistara and G. Romeo, Curr. Org. Chem., 8, 511 (2004); https://doi.org/10.2174/1385272043485828.
- M. Shmidt, A. Reverdito, L. Kremenchuzky, I. Perillo and M. Blanco, Molecules, 13, 831 (2008); https://doi.org/10.3390/molecules13040831.
- K. Mogilaiah and J.U. Rani, Indian J. Chem., 45B, 1051 (2006).
- J. Marco-Contelles, E. Pérez-Mayoral, A. Samadi, M. do Carmo Carreiras and E. Soriano, Chem. Rev., 109, 2652 (2009); https://doi.org/10.1021/cr800482c.
References
B.L. Hayes, Aldrichimica Acta, 37, 66 (2004).
B.M. Sahoo, J. Appl. Pharm., 8, e106 (2016); https://doi.org/10.4172/1920-4159.1000e106.
V. Polshettiwar, M.N. Nadagouda and R.S. Varma, Aust. J. Chem., 62, 16 (2009); https://doi.org/10.1071/CH08404
C.O. Kappe, Chimia, 60, 308 (2006); https://doi.org/10.2533/000942906777836273.
P. Lidström, J. Tierney, B. Wathey and J. Westman, Tetrahedron, 57, 9225 (2001); https://doi.org/10.1016/S0040-4020(01)00906-1.
P. Acosta, E. Butassi, B. Insuasty, A. Ortiz, R. Abonia, S. Zacchino and J. Quiroga, Molecules, 20, 8499 (2015); https://doi.org/10.3390/molecules20058499.
B. Ondruschka, and W. Bonrath, Chimia, 60, 326 (2006); https://doi.org/10.2533/000942906777836246.
S. Caddick, Tetrahedron, 51, 10403 (1995); https://doi.org/10.1016/0040-4020(95)00662-R.
R.S. Varma, Green Chem., 1, 43 (1999); https://doi.org/10.1039/a808223e.
P. Lidstrom, J. Tierney, B. Wathey and J. Westman, Tetrahedron, 57, 9225 (2001); https://doi.org/10.1016/S0040-4020(01)00906-1.
J.T. Leonard, R. Gangadhar, S.K. Gnanasam, S. Ramachandran, M. Saravanan and S.K. Sridhar, Biol. Pharm. Bull., 25, 798 (2002).
I.P. Singh, S. Kumar and S. Gupta, Med. Chem., 13, 430 (2017); https://doi.org/10.2174/1573406412666161228112127.
R.A. Mekheimer, A.M. Abdel Hameed and K.U. Sadek, ARKIVOC, 269 (2007); https://doi.org/10.3998/ark.5550190.0008.d30.
K. Mogilaiah, G. Ramasudhakar and N.V. Reddy, Indian J. Chem., 42B, 1753 (2003).
D. Ramesh, M.T. Chary, E. Laxminarayana and B. Sreenivasuli, Indian J. Chem., 49B, 1271 (2010).
T.R. Ravikumar Naik, H.S. Bhojya Naik, M. Raghavendra and S. G.K. Naik, ARKIVOC, 15, 84 (2006); https://doi.org/10.3998/ark.5550190.0007.f11.
T.R. Ravikumar Naik, H.S. Bhojya Naik, H.R. Prakash Naik, P.J. Bindu, B.G. Harish and V. Krishna, Med. Chem., 5, 5 (2009); https://doi.org/10.2174/157340609789117804.
N.S. Ahmed, K.O. AlFooty and S.S. Khalifah, J. Chem., Article ID 126323 (2014); https://doi.org/10.1155/2014/126323.
S. Abu-Melha, Acta Chim. Slov., 64, 919 (2017); https://doi.org/10.17344/acsi.2017.3617.
R. Álvarez-Manzo, J. Mendoza-Canales, S. Castillo-Cervantes and J. Marín-Cruz, J. Mex. Chem. Soc., 57, 30 (2013); https://doi.org/10.29356/jmcs.v57i1.234.
E.B. Jahromi and A. Mehranpour, J. Hetrocycl. Chem., 54, 1210 (2017); https://doi.org/10.1002/jhet.2694.
A. Madaan, R. Verma, V. Kumar, A.T. Singh, S.K. Jain and M. Jaggi, Arch. Pharm., 348, 837 (2015); https://doi.org/10.1002/ardp.201500237.
S.M. Behalo and G. Mele, J. Hetrocycl. Chem., 54, 295 (2017); https://doi.org/10.1002/jhet.2581.
R. Rajkumar, K. Saravanamani and S.P. Rajendran, J. Chem. Pharm. Sci., 10, 307 (2017).
A. Corsaro, U. Chiacchio, V. Pistara and G. Romeo, Curr. Org. Chem., 8, 511 (2004); https://doi.org/10.2174/1385272043485828.
M. Shmidt, A. Reverdito, L. Kremenchuzky, I. Perillo and M. Blanco, Molecules, 13, 831 (2008); https://doi.org/10.3390/molecules13040831.
K. Mogilaiah and J.U. Rani, Indian J. Chem., 45B, 1051 (2006).
J. Marco-Contelles, E. Pérez-Mayoral, A. Samadi, M. do Carmo Carreiras and E. Soriano, Chem. Rev., 109, 2652 (2009); https://doi.org/10.1021/cr800482c.