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Molecules 2011, 16(6), 5182-5193; doi:10.3390/molecules16065182

Synthesis of Some Novel Pyrazolo[1,5-a]pyrimidine Derivatives and Their Application as Disperse Dyes

1
Natural Science Department, College of Health Science, Public Authority for Applied Education and Training, Kuwait
2
Chemistry Department, Faculty of Science, Kuwait University, P.O. Box 5969, Safat 13060, Kuwait
*
Author to whom correspondence should be addressed.
Received: 1 June 2011 / Revised: 9 June 2011 / Accepted: 15 June 2011 / Published: 22 June 2011
(This article belongs to the Section Organic Synthesis)
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Abstract

A series of novel monoazo-disperse dyes containing pyrazolo[1,5-a]pyrimidine structures were synthesized starting with the coupling reaction between ethyl cyanoacetate and 4-hydroxybenzenediazonium chloride, followed by treatment of the resulting hydrazone product with hydrazine hydrate. The pyrazolohydrazone 6 is then treated with either 2,4-pentandione and enaminonitrile or aryl-substituted enaminoketones to give the target pyrazolo[1,5-a]pyrimidine dyes 7 and 15a-d. Structural assignments to the dyes were made using NMR spectroscopic methods. A new high temperature method, using microwave heating, was employed to apply these dyes to polyester fibers. Most of the dyed fabrics tested displayed moderate light fastness and excellent washing fastness properties.
Keywords: enaminone; pyrazolohydrazone; microwave irradiation; disperse dyes; HMBC 2-D; 2,4-pentandione; enaminonitrile enaminone; pyrazolohydrazone; microwave irradiation; disperse dyes; HMBC 2-D; 2,4-pentandione; enaminonitrile
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Al-Etaibi, A.M.; Al-Awadi, N.A.; El-Apasery, M.A.; Ibrahim, M.R. Synthesis of Some Novel Pyrazolo[1,5-a]pyrimidine Derivatives and Their Application as Disperse Dyes. Molecules 2011, 16, 5182-5193.

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