The Hantzsch Ester Production in a Water-based Biphasic Medium, Using Infrared Irradiation as the Activating Source
DOI:
https://doi.org/10.29356/jmcs.v51i4.1279Keywords:
Hantzsch synthesis, benzaldehydes, 1,4-dihydropyridines, infrared irradiation, green chemistryAbstract
Abstract. The reaction of a wide number of benzaldehydes (1a-n) with ethyl (2a) or methyl (2b) acetoacetate and aqueous ammonia (3) has been carried out in the absence of an organic solvent, and using for the first time infrared irradiation as the heating mode. Thus, under the green chemistry protocole, the corresponding mono-1,4-dihydropyridines (4a-j) and bis-1,4-dihydropyridines (4k-n) were obtained in good yields and short reaction times.
Resumen: En este trabajo se presentan y discuten los resultados obtenidos de la reacción entre varios banzaldehídos (1a-n) con acetoacetato de etilo (2a) o metilo (2b) e hidróxido de amonio (3); lo anterior mediante el protocolo de la química verde: ausencia de disolvente orgánico y empleando irradiación infrarroja como fuente de activación. De esta manera se obtuvieron las correspondientes mono-1,4-dihidropiridinas (4a-j) y bis-1,4-dihidropiridinas (4k-n) con buenos rendimientos y en tiempos cortos de reacción.
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References
1. Anastas, P. T.; Williamson, T. C. Green Chemistry, Frontiers in Benign Chemical Syntheses and Processes; Oxford University Press: Great Britain, 1998.
2. Wender, P. A.; Handy, S. L.; Wright, D. L. Towards the ideal synthesis. Chem. Ind. (London), 1997, 765-769.
3. (a) Eisner, U.; Kuthan, J. Chem. Rev. 1972, 72, 1-42. (b) Stout, D. M.; Meyers, A. I. Chem. Rev. 1982, 82, 223-243.
4. (a) Opie, H.; Gersh, B. J. Drug for the Heart; W.B. Saunders Company: Philadelphia, Pennsylvania, 2001. (b) Tasaka, S.; Ohmori, H.; Gomi, N.; Iino, M.; Machida, T.; Kiue, A.; Naito, S.; Kuwano, M. Bioorg. Med. Chem. Lett. 2001, 11, 275-277. (c) Maya, J. D.; Morello, A.; Repetto, Y.; Téllez, R.; Rodríguez, A.; Zelada, U.; Puebla, P.; Caballero, E.; Medarde, M.; Núñez- Vergara, L. J.; Squella, J. A.; Bonita, M.; Bollo, S.; San Feliciano, A. Com. Biochem. Physiol. Part C 2000, 125, 103-109. (d) Suárez, M.; Verdecia, Y.; Illescas, B.; Martínez-Álvarez, R.; Álvarez, A.; Ochoa, E.; Seoane, C.; Kayali, N.; Martín, N. Tetrahedron 2003, 59, 9179-9186.
5. (a) Phillips, A. P. J. Am. Chem. Soc. 1949, 71, 4003-4007. (b) Maquestiau, A.; Maeyence, A.; Vanden Eynde, J.-J.
Tetrahedron Lett. 1991, 32, 3839-3840. (c) Gordeev, M. F.; Patel, D. V.; Gordon, E. M. J. Org. Chem. 1996, 61, 924-928. (d) Breitenbucher, J. G.; Figliozzi, G. Tetrahedron Lett. 2000, 41, 4311-4315. (e) Öhberg, L.; Westman, J. Synlett 2001, 1296-1298. (f) Jing-Jing, X.; Guan-Wu, W. Synthesis 2005, 2379-2383. (g) Hopes, P. A.; Parker, A. J.; Patel, I. Org. Process Res. Dev. 2006, 10, 808-813.
6. (a) Alcérreca, G.; Sanabria, R.; Miranda, R.; Arroyo, G.A.; Tamariz, J.; Delgado, F. Synth. Commun. 2000, 30, 1295-1301. (b) Salmón, M.; Osnaya, R.; Gómez, L.; Arroyo, G.A.; Delgado, F.; Miranda, R. Rev. Soc. Quím. Méx. 2001, 45, 206-207. (c) Osnaya, R.; Arroyo, G. A.; Parada, L.; Delgado, F.; Trujillo, J.; Salmón, M.; Miranda, R. Arkivoc 2003, ix, 112-117. (d) Vázquez, M.A.; Landa, M.; Reyes, L.; Miranda, R.; Tamariz, J.; Delgado, F. Synth. Commun. 2004, 34, 2705-2718. (e) Ballesteros, L.; Noguez, O.; Arroyo, G.; Velasco, B.; Delgado, F.; Miranda, R. J. Mex. Chem. Soc. 2005, 49, 92-95. (f) Sharma, G. V. M.; Reddy, K. L.; Lakshmi, P. S.; Krishna, P. R. Synthesis 2006, 55-58. (g) Vanden, J. J.; Mayence, A., Molecules 2003, 8, 381-391.
7. (a) Ehrhardt, J. D.; Ziegler, J.M. Biomed. Environ. Mass Spectrom. 1988, 15, 525-528. (b) Hamdan, M.; Scandola, M.; Franchi, D.; Tarzia, G.; Gaviraghi, G. Rapid Commun. Mass Spectrom. 1991, 5, 493-498. (c) Hamdan, M.; Scandola, M.; Tarzia, G. Org. Mass Spectrom. 1992, 27, 724-729. (d) López-Alarcón, C.; Squella; J. A.; Núñez-Vergara, L. J.; Báez, H.; Camargo, C. Rapid Commun. Mass Spectrom. 2002, 16, 2229-2238.
8. Kuthan, J.; Kurfürst, A.; Prosek, Z.; Palecek, J. Coll. Czechoslov. Chem. Commun. 1978, 43, 1068-1079.
9. Mukherjee, A. S.; Akhtar, M. S.; Sharma, V. L.; Seth, M.; Bhaduri, A. P.; Agnihotri, A.; Mehrotra, P. K.; Kamboj, V. P. J. Med. Chem. 1989, 32, 2297-2300.
10. Phillips, A. J. Am. Chem. Soc. 1950, 72, 2780.
11. Balboni, B.; Valenti, P.; Da Re, P.; Rovati, L. C.; Makovec, F. Pharmazie 1988, 43, 318-320.
12. Tu, S.; Miao, Ch.; Fang, F.; Youjian, F.; Li, T.; Zhuang, Q.; Zhang, X.; Zhu, S.; Shi, D. Bioorg. Med. Chem. Lett. 2004, 14, 1533-1536.
13. Salehi, H.; Guo, Q.-X. Synth. Commun. 2004, 34, 4349-4357.
14. Zhu, S.; Tu, S.; Gao, Y.; Miao, C.; Li, T.; Zhang, X.; Fang, F.; Shi, D. Synth. Commun. 2005, 35, 1011-1015.
15. Gómez, R.; Ramírez-San Juan, E.; Miranda, R.; Villalobos- Molina, R.; Delgado, F.; Osnaya, R.; Trujillo-Ferrara, J. G. Med. Chem. 2006, 2, 527-534,
16. (a) Singh, H.; Sarin, R.; Singh, K. Heterocycles 1986, 24, 3039- 3042. (b) Krauze, A. Khim. Geterotskl. Soedin. 1984, 1504-1508. (c) Loev, B.; Goodman, M. M. J. Heterocyclic Chem. 1975, 12, 363-365. (d) Loev, B.; Snader, K. M. J. Org. Chem. 1965, 30, 1914-1916. (e) Loev, B.; Goodman, M. M.; Snader, K. M.; Tedeschi, R.; Macko, E. J. Med. Chem. 1974, 17, 956-965. (f) Yadav, J. S.; Subba, R. B. V.; Thirupathi, R. Synth. Commun. 2001, 31, 425-430. (g) Kidwai, M.; Saxena, S.; Mohan, R.; Venkataramanan, R. J. Chem. Soc., Perkin Trans. 1, 2002, 1845-1846; (h) Bakibaev, A. A. Zh. Org. Khim. 1991, 27, 854-859.
17. Hinkel, L. E.; Ayling, E. E.; Morgan, W. H. J. Chem. Soc. 1931, 1835-1841.
18. (a) Hinkel, L. E.; Madel, W. R. J. Chem. Soc. 1929, 750-754. (b) Chem. Abst. 1966, 65, 20092h. (c) Kametani, T.; Ogasawara, K.; Kozuka, A. Yakugaku Zasshi. 1966, 86, 815.
19. Hinkel, L. E.; Cremer, H. W. J. Chem. Soc. 1920, 137-140.
20. Tirzite, G. Khim. Geterotskl. Soedin. 1987, 68-69.
21. Watanabe, Y.; Shiota, K.; Hoshiko, T. Synthesis 1983, 761.
2. Wender, P. A.; Handy, S. L.; Wright, D. L. Towards the ideal synthesis. Chem. Ind. (London), 1997, 765-769.
3. (a) Eisner, U.; Kuthan, J. Chem. Rev. 1972, 72, 1-42. (b) Stout, D. M.; Meyers, A. I. Chem. Rev. 1982, 82, 223-243.
4. (a) Opie, H.; Gersh, B. J. Drug for the Heart; W.B. Saunders Company: Philadelphia, Pennsylvania, 2001. (b) Tasaka, S.; Ohmori, H.; Gomi, N.; Iino, M.; Machida, T.; Kiue, A.; Naito, S.; Kuwano, M. Bioorg. Med. Chem. Lett. 2001, 11, 275-277. (c) Maya, J. D.; Morello, A.; Repetto, Y.; Téllez, R.; Rodríguez, A.; Zelada, U.; Puebla, P.; Caballero, E.; Medarde, M.; Núñez- Vergara, L. J.; Squella, J. A.; Bonita, M.; Bollo, S.; San Feliciano, A. Com. Biochem. Physiol. Part C 2000, 125, 103-109. (d) Suárez, M.; Verdecia, Y.; Illescas, B.; Martínez-Álvarez, R.; Álvarez, A.; Ochoa, E.; Seoane, C.; Kayali, N.; Martín, N. Tetrahedron 2003, 59, 9179-9186.
5. (a) Phillips, A. P. J. Am. Chem. Soc. 1949, 71, 4003-4007. (b) Maquestiau, A.; Maeyence, A.; Vanden Eynde, J.-J.
Tetrahedron Lett. 1991, 32, 3839-3840. (c) Gordeev, M. F.; Patel, D. V.; Gordon, E. M. J. Org. Chem. 1996, 61, 924-928. (d) Breitenbucher, J. G.; Figliozzi, G. Tetrahedron Lett. 2000, 41, 4311-4315. (e) Öhberg, L.; Westman, J. Synlett 2001, 1296-1298. (f) Jing-Jing, X.; Guan-Wu, W. Synthesis 2005, 2379-2383. (g) Hopes, P. A.; Parker, A. J.; Patel, I. Org. Process Res. Dev. 2006, 10, 808-813.
6. (a) Alcérreca, G.; Sanabria, R.; Miranda, R.; Arroyo, G.A.; Tamariz, J.; Delgado, F. Synth. Commun. 2000, 30, 1295-1301. (b) Salmón, M.; Osnaya, R.; Gómez, L.; Arroyo, G.A.; Delgado, F.; Miranda, R. Rev. Soc. Quím. Méx. 2001, 45, 206-207. (c) Osnaya, R.; Arroyo, G. A.; Parada, L.; Delgado, F.; Trujillo, J.; Salmón, M.; Miranda, R. Arkivoc 2003, ix, 112-117. (d) Vázquez, M.A.; Landa, M.; Reyes, L.; Miranda, R.; Tamariz, J.; Delgado, F. Synth. Commun. 2004, 34, 2705-2718. (e) Ballesteros, L.; Noguez, O.; Arroyo, G.; Velasco, B.; Delgado, F.; Miranda, R. J. Mex. Chem. Soc. 2005, 49, 92-95. (f) Sharma, G. V. M.; Reddy, K. L.; Lakshmi, P. S.; Krishna, P. R. Synthesis 2006, 55-58. (g) Vanden, J. J.; Mayence, A., Molecules 2003, 8, 381-391.
7. (a) Ehrhardt, J. D.; Ziegler, J.M. Biomed. Environ. Mass Spectrom. 1988, 15, 525-528. (b) Hamdan, M.; Scandola, M.; Franchi, D.; Tarzia, G.; Gaviraghi, G. Rapid Commun. Mass Spectrom. 1991, 5, 493-498. (c) Hamdan, M.; Scandola, M.; Tarzia, G. Org. Mass Spectrom. 1992, 27, 724-729. (d) López-Alarcón, C.; Squella; J. A.; Núñez-Vergara, L. J.; Báez, H.; Camargo, C. Rapid Commun. Mass Spectrom. 2002, 16, 2229-2238.
8. Kuthan, J.; Kurfürst, A.; Prosek, Z.; Palecek, J. Coll. Czechoslov. Chem. Commun. 1978, 43, 1068-1079.
9. Mukherjee, A. S.; Akhtar, M. S.; Sharma, V. L.; Seth, M.; Bhaduri, A. P.; Agnihotri, A.; Mehrotra, P. K.; Kamboj, V. P. J. Med. Chem. 1989, 32, 2297-2300.
10. Phillips, A. J. Am. Chem. Soc. 1950, 72, 2780.
11. Balboni, B.; Valenti, P.; Da Re, P.; Rovati, L. C.; Makovec, F. Pharmazie 1988, 43, 318-320.
12. Tu, S.; Miao, Ch.; Fang, F.; Youjian, F.; Li, T.; Zhuang, Q.; Zhang, X.; Zhu, S.; Shi, D. Bioorg. Med. Chem. Lett. 2004, 14, 1533-1536.
13. Salehi, H.; Guo, Q.-X. Synth. Commun. 2004, 34, 4349-4357.
14. Zhu, S.; Tu, S.; Gao, Y.; Miao, C.; Li, T.; Zhang, X.; Fang, F.; Shi, D. Synth. Commun. 2005, 35, 1011-1015.
15. Gómez, R.; Ramírez-San Juan, E.; Miranda, R.; Villalobos- Molina, R.; Delgado, F.; Osnaya, R.; Trujillo-Ferrara, J. G. Med. Chem. 2006, 2, 527-534,
16. (a) Singh, H.; Sarin, R.; Singh, K. Heterocycles 1986, 24, 3039- 3042. (b) Krauze, A. Khim. Geterotskl. Soedin. 1984, 1504-1508. (c) Loev, B.; Goodman, M. M. J. Heterocyclic Chem. 1975, 12, 363-365. (d) Loev, B.; Snader, K. M. J. Org. Chem. 1965, 30, 1914-1916. (e) Loev, B.; Goodman, M. M.; Snader, K. M.; Tedeschi, R.; Macko, E. J. Med. Chem. 1974, 17, 956-965. (f) Yadav, J. S.; Subba, R. B. V.; Thirupathi, R. Synth. Commun. 2001, 31, 425-430. (g) Kidwai, M.; Saxena, S.; Mohan, R.; Venkataramanan, R. J. Chem. Soc., Perkin Trans. 1, 2002, 1845-1846; (h) Bakibaev, A. A. Zh. Org. Khim. 1991, 27, 854-859.
17. Hinkel, L. E.; Ayling, E. E.; Morgan, W. H. J. Chem. Soc. 1931, 1835-1841.
18. (a) Hinkel, L. E.; Madel, W. R. J. Chem. Soc. 1929, 750-754. (b) Chem. Abst. 1966, 65, 20092h. (c) Kametani, T.; Ogasawara, K.; Kozuka, A. Yakugaku Zasshi. 1966, 86, 815.
19. Hinkel, L. E.; Cremer, H. W. J. Chem. Soc. 1920, 137-140.
20. Tirzite, G. Khim. Geterotskl. Soedin. 1987, 68-69.
21. Watanabe, Y.; Shiota, K.; Hoshiko, T. Synthesis 1983, 761.
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