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

Rearrangement of o-Nitrobenzaldehyde in the Hantzsch Reaction

1email, 1, 1, 1, 1, 1, 2 and 3,* email
Received: 13 December 2000; in revised form: 6 June 2001 / Accepted: 16 July 2001 / Published: 21 July 2001
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
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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MDPI and ACS Style

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.

AMA Style

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.

Chicago/Turabian Style

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.

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