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Molecules 2001, 6(8), 683-693; doi:10.3390/60800683

Rearrangement of o-Nitrobenzaldehyde in the Hantzsch Reaction

1, 1, 1, 1, 1, 2 and 3,*
1 Laboratorio de Química Medicinal, Facultad de Estudios Superiores Cuautitlán, Universidad Nacional Autónoma de México, Mexico 2 Facultad de Química, Universidad Autónoma del Estado de México, Mexico 3 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 / Revised: 6 June 2001 / Accepted: 16 July 2001 / Published: 21 July 2001
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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 Hantzsch reaction; cyclization; indole derivatives; quinoline derivatives
This is an open access article distributed under the Creative Commons Attribution License (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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.

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