Facile and Simple Syntheses of Heterocyclic Compounds Based on Pyridine and Pyrazolopyridine Derivatives

S. A. Swelam¹, N. S. El-Said¹, A. S. Aly¹ and A. M. Abdel-Fatth²

¹Photochemistry Department, National Research Centre, Dokki, Giza Egypt. ²Faculty of Science Giza, University Giza Egypt.

ABSTRACT:

In one pot synthesis, cyanopyridone 4 was achieved upon refluxing of p-methoxybenz-aldhyde, 2-butanon, ethyl cyanoacetate and ammonium acetate in ethanol. The chloro- derivative 5 was obtained, 5 under went neocleophilic substitution reaction with morpholine, and piprazine to give 6 and 7 respectively. Cyclocondensation reactions of 9 with active methylene compounds afforded 1,5,8a,9-tetraaza-fluorene derivatives (10a,b,11,12). Compound 13 obtained upon heating of compound 9 with benzoin in presence of phosphorous oxychloride. Synthesis of 14 was also achieved. Diazotization of 9 and its reactions with cyano compounds, a-haloketones and benzensulphonylacetophenone gave compounds 16,17,18a,b and 19,respectively. When diazonium salt 15 reacted with phenacyl bromide in pyridine gave the corresponding indene derivative 21.

KEYWORDS:

cyanopyridone; active methylene; neocleophilic substitution; phenacyl bromide

Download this article as: 

Copy the following to cite this article: Swelam S. A, El-Said N. S, Aly A. S. Abdel-Fatth A. M. Facile and Simple Syntheses of Heterocyclic Compounds Based on Pyridine and Pyrazolopyridine Derivatives. Orient J Chem 2008;24(1).

Copy the following to cite this URL: Swelam S. A, El-Said N. S, Aly A. S. Abdel-Fatth A. M. Facile and Simple Syntheses of Heterocyclic Compounds Based on Pyridine and Pyrazolopyridine Derivatives. Orient J Chem 2008;24(1). Available from: http://www.orientjchem.org/?p=23020