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
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,*
Received: 13 December 2000; in revised form: 6 June 2001 / Accepted: 16 July 2001 / Published: 21 July 2001
Download PDF [68 KB, uploaded 18 June 2014]
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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Export to BibTeX |
EndNote


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.


Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert