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Isoniazida Antituberculoso
Sulfapiridina Antibactericida
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Davicil Fungicida
Mecanismo de la sntesis de Hantzsch para obtener 1,4-Dihidropiridinas Dos intermediarios clave: 1) Producto de la Condensacin de Knoevenagel, formacin de un compuesto carbonlico ,-insaturado:
1,4-DIHIDROPIRIDINAS ASIMTRICAS
Efficient Synthesis of Hantzsch Esters and Polyhydroquinoline Derivatives in Aqueous Micelles A. Kumar, R. A. Maurya, Synlett, 2008, 883-885.
'In situ'; Generated 'HCl'; - An Efficient Catalyst for Solvent-Free Hantzsch Reaction at Room Temperature: Synthesis of New Dihydropyridine Glycoconjugates G. V. M. Sharma, K. L. Reddy, P. S. Lakshmi, P. R. Krishna, Synthesis, 2006, 55-58.
One-Pot Synthesis of 1,4-Dihydropyridines via a Phenylboronic Acid Catalyzed Hantzsch ThreeComponent Reaction A. Debache, R. Boulcina, A. Belfaitah, S. Rhouati, B. Carboni, Synlett, 2008, 509-512.
Covalently Anchored Sulfonic Acid on Silica Gel as an Efficient and Reusable Heterogeneous Catalyst for the One-Pot Synthesis of Hantzsch 1,4-Dihydropyridines under Solvent-Free Conditions R. Gupta, R. Gupta, S. Paul, A. Loupy, Synthesis, 2007, 2835-2838.
Yb(OTf)3 catalyzed an efficient, operationally simple and environmentally benign Hantzsch reaction via a four-component coupling reaction of aldehydes, dimedone, ethyl acetoacetate and ammonium acetate at ambient temperature to yield polyhydroquinoline derivatives in excellent yield. L.-M. Wang, J. Sheng, L. Zhang, J.-W. Han, Z.-Y. Fan, H. Tian, C.-T. Qian, Tetrahedron, 2005, 61, 1539-1543.
4-Substituted-1,4-dihydropyridines are readily and efficiently aromatized in only one minute using commercial manganese dioxide in the absence of an inorganic support at 100 C under microwave irradiation. This rapid procedure gives the dehydrogenated or 4-dealkylated product in excellent yield. M. C. Bagley, M. C. Lubinu, Synthesis, 2006, 1283-1288.
Hantzsch 1,4-dihydropyridines undergo smooth aromatization catalyzed by iodoxybenzoic acid (IBX) to afford the corresponding pyridine derivatives in high yields. All the reactions were carried out in DMSO solvent at 80-85 C for a period of two to four hours to complete conversion of the substrates. J. S. Yadav, B. V. S. Reddy, A. K. Basak, G. Baishya, A. V. Narsaiah, Synthesis, 2006, 451-454.
bmim]OH, a basic ionic liquid, efficiently promotes a one-pot condensation of aldehydes, malononitrile, and thiophenols to produce highly substituted pyridines in high yields. The ionic liquid can be recovered and recycled. B. C. Ranu, R. Jana, S. Sowmiah, J. Org. Chem., 2007, 72, 3152-3154.
SNTESIS DE KRHNKE
W. Zecher, F. Krhnke, Ber. 94, 690, 698 (1961); idem., Angew. Chem. Int. Ed. 1, 626 (1962).
Sintesis de Bohlmann-Rahtz
La sntesis de Bohlmann-Rahtz permite obtener piridinas sustituidas en dos pasos. El primer paso es la condensacin de una enamina con una etinilcetonas para formar un aminodieno como intermediario el cual posteriormente por medio de una isomera E/Z, sufre una reaccin de ciclodeshidratacin para formar finalmente piridinas 2,3,6trisustitudas.
Isomera E Z y ciclodeshidratacin
A NEW MODIFICATION OF THE BOHLMANN-RAHTZ PYRIDINE SYNTHESIS M. C. Bagley, J. W. Dale, J. Bower, Synlett, 2001, 1149-1151.
A new mild method for the one-pot synthesis of pyridines X. Xiong, M. C. Bagley, K. Chapaneri, Tetrahedron Lett., 2004, 45, 6121-6124.
A new mild method for the one-pot synthesis of pyridines X. Xiong, M. C. Bagley, K. Chapaneri, Tetrahedron Lett., 2004, 45, 6121-6124.
A new one-step synthesis of pyridines under microwave-assisted conditions M. C. Bagley, R. Lunn, X. Xiong, Tetrahedron Lett., 2002, 43, 8331-8334.
Sntesis de Guareschi-Thorpe
Icilio Guareschi (24 de diciembre, 1847 a 20 de junio de 1918), qumico italiano Jocelyn Field Thorpe (1 de diciembre, 1872 a 10 de junio de 1940) fue un qumico ingls
I. Guareschi, Mem. Reale Accad. Sci. Torino II, 46, 7, 11, 25 (1896) I. Guareschi, Mem. Reale Accad. Sci. Torino II, 55, 287 (1905) J. F. Thorpe et al., J. Chem. Soc. 99, 422 (1911); 115, 686 (1919); 117, 1465 (1920); 121, 1765,1821 (1922); 127, 2358 (1925)
PROPIEDADES QUMICAS
Yoduro de 1-aminopiridinio
N-xido de la priridina
Tribromuro de priridinio
4-dimetilaminopiridina (DMPA)
N-SUSTITUCIN N-sustitucin
percido
Bromuro de 1-etilpiridinio
Cloruro de 1-acetilpiridinio
N-xido de la lpiridina
NITRACIN
NITRACIN
SULFONACIN
HALOGENACIN
Bt = benzotriazol
REACCIN DE CHICHIBABIN
Aleksy Yevgnyevich Chichibbin (EN RUSO: ; Villa de Kuzemino, en la actualidad Poltava Oblast, 29 de marzo 1871; Paris 15 de agosto, 1945) fue un qumico orgnico Ruso (Sovitico). Su nombre tambin se escribe Alexei Yevgenievich Chichibabin y como Alexei Euguenievich Tchitchibabine
A. E. Chichibabin and O. A. Zeide (1914). Zhur. Russ. Fiz. Khim. Obshch (J. Russ. Phys. Chem. Soc.) 46: 1212.
REACCIONES DE ALQUILPIRIDINAS
5-azaindol