Next Article in Journal
An Efficient and Chemoselective Method for Oximination of β-Diketones Under Mild and Heterogeneous Conditions
Previous Article in Journal
Synthesis of new Bis- and Tetra-Acridines
Article Menu

Export Article

Open AccessArticle
Molecules 2001, 6(8), 683-693;

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 / Revised: 6 June 2001 / Accepted: 16 July 2001 / Published: 21 July 2001
Full-Text   |   PDF [68 KB, uploaded 18 June 2014]   |  


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. View Full-Text
Keywords: Hantzsch reaction; cyclization; indole derivatives; quinoline derivatives Hantzsch reaction; cyclization; indole derivatives; quinoline derivatives

Figure 1

This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

Share & Cite This Article

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.

Show more citation formats Show less citations formats

Related Articles

Article Metrics

Article Access Statistics



[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top