Solvent- and Catalyst-Free One-Pot Green Bound-Type Fused Bis-Heterocycles Synthesis via Groebke-Blackburn-Bienaymé Reaction/SN Ar/Ring-Chain Azido-Tautomerization Strategy

ACS Omega
Miguel Ángel Claudio-CatalánRocío Gámez-Montaño

Abstract

A new, efficient, green, endogenous water-triggered, solvent- and catalyst-free ultrasound-assisted one-pot Groebke-Blackburn-Bienaymé reaction/SNAr/ring-chain azido-tautomerization strategy to synthesize bound-type fused bis-heterocycles imidazo or benzo[d]imidazo[2,1-b]thiazoles and 1,5-disubstituted tetrazole (1,5-DsT) containing quinoline moiety is described, which allows synthesis of two types of fused heterocycles in one step under mild green conditions. Antibacterial and antiamebic activities of selected newly synthesized compounds were carried out against three bacterial species: Gram-positive bacterium Staphylococcus aureus ATCC 6538 and Gram-negative bacteria Pseudomonas aeruginosa ATCC 13384 and Escherichia coli O55 and against one amebic species: Entamoeba histolytica.

References

Sep 25, 2008·Journal of Combinatorial Chemistry·Miroslav SouralViktor Krchnák
Aug 27, 2014·Canadian Journal of Gastroenterology & Hepatology·Christopher SkappakPaul L Beck
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Nov 5, 2016·The Journal of Organic Chemistry·M V Basavanag UnnamatlaRocío Gámez-Montaño

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Citations

Feb 7, 2020·Pharmaceuticals·Micheline DrayeRomain Duwald
Jan 23, 2021·Organic & Biomolecular Chemistry·Biswajita Baruah, Mohit L Deb
Oct 13, 2019·European Journal of Medicinal Chemistry·Feng GaoGang Huang
Nov 15, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Shrikant G PharandeRocío Gámez-Montaño

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Methods Mentioned

BETA
X-ray
column chromatography
1
silica gel column chromatography
NMR

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