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Rearrangement of o-Nitrobenzaldehyde in the Hantzsch Reaction
Laboratorio de Química Medicinal, Facultad de Estudios Superiores Cuautitlán, Universidad Nacional Autónoma de México, Mexico
Facultad de Química, Universidad Autónoma del Estado de México, Mexico
Instituto de Química, Universidad Nacional Autónoma de México, Apartado Postal 70-213, Coyoacán, México, D.F. CP 04510, México
* Author to whom correspondence should be addressed.
Received: 13 December 2000; in revised form: 6 June 2001 / Accepted: 16 July 2001 / Published: 21 July 2001
Abstract: The reaction of 5-hydroxy-2-nitrobenzaldehyde with ethyl acetoacetate in ammonia gave the two expected isomeric 1,4- and 1,2-dihydropyridines resulting from the normal Hantzsch reaction. However, the combination of 2-nitrobenzaldehyde with ethyl acetoacetate under the same conditions yielded four products: the two normal isomeric dihydropyridines and two tricyclic compounds. When we attempted to independently synthesize the two tricyclic compounds by reductive cyclization of 4-(2-nitrophenyl)-2,6-dimethyl-3,5-dicarbetoxy-1,4-dihydropyridine and 2-(2-nitrophenyl)-4,6-dimethyl-3,5-dicarbetoxy-1,2-dihydropyridine with tin (II) chloride in hydrochloric acid media, we obtained instead an indole and a quinoline derivative, respectively.
Keywords: Hantzsch reaction; cyclization; indole derivatives; quinoline derivatives
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Angeles, E.; Santillán, H.; Menconi, I.; Martínez, I.; Ramírez, A.; Velázquez, A.; López- Castañares, R.; Martínez, R. Rearrangement of o-Nitrobenzaldehyde in the Hantzsch Reaction. Molecules 2001, 6, 683-693.
Angeles E, Santillán H, Menconi I, Martínez I, Ramírez A, Velázquez A, López- Castañares R, Martínez R. Rearrangement of o-Nitrobenzaldehyde in the Hantzsch Reaction. Molecules. 2001; 6(8):683-693.
Angeles, E.; Santillán, H.; Menconi, I.; Martínez, I.; Ramírez, A.; Velázquez, A.; López- Castañares, R.; Martínez, R. 2001. "Rearrangement of o-Nitrobenzaldehyde in the Hantzsch Reaction." Molecules 6, no. 8: 683-693.