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Article

Synthesis, Reactions and Biological Evaluation of Some Novel 5-Bromobenzofuran-Based Heterocycles

1Chemistry Department, Faculty of Science, Al-Azhar University, Nasr City, Cairo, Egypt


World Journal of Organic Chemistry. 2014, 2(1), 9-17
DOI: 10.12691/wjoc-2-1-2
Copyright © 2014 Science and Education Publishing

Cite this paper:
Ahmed Hamdy Halawa. Synthesis, Reactions and Biological Evaluation of Some Novel 5-Bromobenzofuran-Based Heterocycles. World Journal of Organic Chemistry. 2014; 2(1):9-17. doi: 10.12691/wjoc-2-1-2.

Correspondence to: Ahmed  Hamdy Halawa, Chemistry Department, Faculty of Science, Al-Azhar University, Nasr City, Cairo, Egypt. Email: ahmedhalawa_79@yahoo.com

Abstract

Condensation of 2-acetyl-5-bromobenzofuran with hydrazine derivatives 2a,b afforded hydrazone derivatives 3a,b, which reacted with alkyl halides4a,b to yield ethylidene derivatives 5a,b. Also, 3a reacted with hydrazonyl halides6a,b to give 1,3,4-thiadiazole derivatives 9a,b. Thiosemicarbazone3b was reacted with acetic anhydride and halogenated compounds to afford the corresponding heterocyclic derivatives 10, 11a,b, 12-17 and 18a,b.Moreover, interaction of 16 with tetracyanoethylene and salicyldehyde derivatives furnished 24 and 26a,b, respectively. Finally, reaction of 16 with DMF-DMA afforded enaminone29, which on treatment with different heterocyclic amines yielded 31 and 33 respectively. Some of the newly synthesized compounds showed promising antimicrobial activity.

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References

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Article

A Convenient Synthesis of Ethyl 1-Amino-3-(Substituted Phenyl)-2-Cyano-3H-Benzo[4,5]Thiazolo-[3,2-a]Pyridine-4-Carboxylate Derivatives and Some of their Reactions

1Chemistry Department, Faculty of Medicine, Jazan University, Jazan, Saudi Arabia

2Chemistry Department, Faculty of Science, Al-Azhar University, Nasr City, Cairo, Egypt


World Journal of Organic Chemistry. 2014, 2(1), 1-8
DOI: 10.12691/wjoc-2-1-1
Copyright © 2014 Science and Education Publishing

Cite this paper:
Hany M. Mohamed. A Convenient Synthesis of Ethyl 1-Amino-3-(Substituted Phenyl)-2-Cyano-3H-Benzo[4,5]Thiazolo-[3,2-a]Pyridine-4-Carboxylate Derivatives and Some of their Reactions. World Journal of Organic Chemistry. 2014; 2(1):1-8. doi: 10.12691/wjoc-2-1-1.

Correspondence to: Hany  M. Mohamed, Chemistry Department, Faculty of Medicine, Jazan University, Jazan, Saudi Arabia. Email: hanysm83@yahoo.com

Abstract

The titled compounds were prepared by interaction of ethyl 2-(benzo[d]thazol-2-yl)acetate (3) with different arylidinemalononitrile derivatives (4a-c) in EtOH/TEA solution at room temperature. When 3 was treated with 2-(ethoxymethylene)-malononitrile (4f) under same reaction conditions, the ethyl iminothiazolopyridine-4-carboxylate (6) was obtained. Ethyl (amino(methoxy)methyl)-3-(substitutedphenyl)-1-oxo-1H-benzo[4,5]thiazole[3,2-a]pyridine-4-carboxylate (8a,b) was obtained from reaction of 3 with different cyanoacrylate derivatives (7a,b) in MeOH/TEA at room temperature, while the diethyl thiazolo[3,2-a]pyridine-4-carboxylate derivative (8c) was obtained under same reaction conditions. The amino-imino derivative (10) was also prepared and used to synthesis new pyrido[3,2-e][1,2,4]triaziolo[1,5-c]pyrimidine-5-carboxylate derivatives (12). The structures of all the newly synthesized compounds were confirmed based on their elemental analysis and spectroscopic data.

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References

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