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Molecules 2014, 19(2), 2637-2654; https://doi.org/10.3390/molecules19022637

Synthesis of A New Class of Pyridazin-3-one and 2-Amino-5-arylazopyridine Derivatives and Their Utility in the Synthesis of Fused Azines

1
Chemistry Department, Faculty of Science, Kuwait University, P.O. Box 5969, Safat 13060, Kuwait
2
Chemistry Department, Faculty of Science, Fayoum University, El-Fayoum 63514, A. R., Egypt
*
Author to whom correspondence should be addressed.
Received: 27 January 2014 / Revised: 11 February 2014 / Accepted: 17 February 2014 / Published: 24 February 2014
(This article belongs to the Section Organic Chemistry)
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Abstract

A general route for the synthesis of a novel class of pyridazin-3-one derivatives 3 by the reaction in acetic anhydride between 3-oxo-2-arylhydrazonopropanals 1 and some active methylene compounds like p-nitrophenylacetic acid and cyanoacetic acid was established. Under these conditions the pyridazin-3-one derivatives 3 were formed as the sole isolable products in excellent yield. The 6-acetyl-3-oxopyridazine derivative 3l was reacted with DMF-DMA to afford the corresponding enaminone derivative 4, which reacts with a variety of aminoazoles to afford the corresponding azolo[1,5-a]pyrimidine derivatives 57. Also, in order to explore the viability and generality of a recently uncovered reaction between 3-oxo-2-arylhydrazonopropanals and active methylene compounds, a variety of 2-amino-6-aryl-5-arylazo-3-aroylpyridines 1619 were prepared by reacting 3-oxo-2-arylhydrazonopropanals with miscellaneous active methylene compounds like 3-oxo-3-phenylpropionitrile, hetaroylacetonitriles and cyanoacetamides. These 2-aminopyridine derivatives undergo smooth reactions with cyanoacetic acid that led to the formation in high yield of a new class of 1,8-naphthyridine derivatives 24. The structures of all new substances prepared in this investigation were determined by the different analytical spectroscopic methods, in addition to the X-ray crystallographic analysis. View Full-Text
Keywords: pyridazin-3-one; 2-amino-5-arylazopyridine; azolo[1,5-a]pyrimidine; DMF-DMA; cyanoacetic acid; 1,8-naphthyridine pyridazin-3-one; 2-amino-5-arylazopyridine; azolo[1,5-a]pyrimidine; DMF-DMA; cyanoacetic acid; 1,8-naphthyridine
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Ibrahim, H.M.; Behbehani, H. Synthesis of A New Class of Pyridazin-3-one and 2-Amino-5-arylazopyridine Derivatives and Their Utility in the Synthesis of Fused Azines. Molecules 2014, 19, 2637-2654.

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