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

Rearrangement of o-Nitrobenzaldehyde in the Hantzsch Reaction

1
,
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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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 Hantzsch reaction; cyclization; indole derivatives; quinoline derivatives
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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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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