Rearrangement of o-Nitrobenzaldehyde in the Hantzsch Reaction 英文参考文献.docVIP

Molecules 2001, 6, 683-693 molecules ISSN 1420-3049 Rearrangement of o-Nitrobenzaldehyde in the Hantzsch Reaction? E. Angeles1, H. Santillán1, I. Menconi1, I. Martínez1, A. Ramírez1, A. Velázquez1, R. López- Casta?ares2 and R. Martínez3,*. 1 Laboratorio de Química Medicinal, Facultad de Estudios Superiores Cuautitlán, Universidad Nacional Autónoma de México; E-mail: angeles@servidor.unam.mx. 2 Facultad de Química, Universidad Autónoma del Estado de México. 3 Instituto de Química, Universidad Nacional Autónoma de México, Apartado Postal 70-213, Coyoacán, México, D.F. CP 04510, México. ? Contribution No. 1736 from the Instituto de Química, UNAM * Author to whom correspondence should be addressed; E-mail: robmar@servidor.unam.mx . Received: 13 December 2000; in revised form 6 June 2001 / Accepted: 16 July 2001 /Published: 21 July 2001 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  Molecules 2001, 6 684 Introduction Dihydropyridine derivatives display a broad spectrum of medicinal activities, mainly as antihypertensive and antiarrhythmic drugs. They are also used as st