Microwave Assisted Condensation Reactions of 2-Aryl Hydrazonopropanals with Nucleophilic Reagents and Dimethyl Acetylenedicarboxylate

doi:10.3390/12082061

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Molecules 2007, 12(8), 2061-2079; doi:10.3390/12082061

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Microwave Assisted Condensation Reactions of 2-Aryl Hydrazonopropanals with Nucleophilic Reagents and Dimethyl Acetylenedicarboxylate

Khadijah M. Al-Zaydi* and Rita M. Borik

Department of Chemistry, Girl’s College of Education, Jeddah, P.O. 50918 Jeddah 21533, Kingdom of Saudi Arabia

* Author to whom correspondence should be addressed.

Received: 16 February 2007; in revised form: 26 May 2007 / Accepted: 1 June 2007 / Published: 24 August 2007

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Abstract: The reaction of methyl ketones 1a-g with dimethylformamide dimethylacetal (DMFDMA) afforded the enaminones 2a-g, which were coupled with diazotized aromatic amines 3a,b to give the corresponding aryl hydrazones 6a-h. Condensation of compounds 6a-h with some aromatic heterocyclic amines afforded iminoarylhydrazones 9a-m. Enaminoazo compounds 12a,b could be obtained from condensation of 6c with secondary amines. The reaction of 6e,h with benzotriazolylacetone yielded 14a,b. Also, the reaction of 6a,b,d-f,h with glycine and hippuric acid in acetic anhydride afforded pyridazinone derivatives 17a-f. Synthesis of pyridazine carboxylic acid derivatives 22a,b from the reaction of 6b,e with dimethyl acetylenedicarboxylate (DMAD) in the presence of triphenylphosphine at room temperature is also reported. Most of these reactions were conducted under irradiation in a microwave oven in the absence of solvent in an attempt to improve the product yields and to reduce the reaction times.

Keywords: 2-Arylhydrazonopropanals; heterocyclic amines; active methylene; microwave irradiation

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MDPI and ACS Style

Al-Zaydi, K.M.; Borik, R.M. Microwave Assisted Condensation Reactions of 2-Aryl Hydrazonopropanals with Nucleophilic Reagents and Dimethyl Acetylenedicarboxylate. Molecules 2007, 12, 2061-2079.

AMA Style

Al-Zaydi KM, Borik RM. Microwave Assisted Condensation Reactions of 2-Aryl Hydrazonopropanals with Nucleophilic Reagents and Dimethyl Acetylenedicarboxylate. Molecules. 2007; 12(8):2061-2079.

Chicago/Turabian Style

Al-Zaydi, Khadijah M.; Borik, Rita M. 2007. "Microwave Assisted Condensation Reactions of 2-Aryl Hydrazonopropanals with Nucleophilic Reagents and Dimethyl Acetylenedicarboxylate." Molecules 12, no. 8: 2061-2079.

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