Multicomponent reactions (MCRs) have significant relevance in the field of synthetic chemistry, and in recent times one of the MCR variants, named the Groebke-Blackburn-Bienaymé (GBB) reaction, has attracted massive attention for the synthesis of biologically important scaffolds. The present review elaborates on the chemical advancement reported for the GBB reaction with an emphasis on the role of various catalytic systems. Further, the role of the GBB reaction has been redefined as a standard protocol for the synthesis of an array of potential bioactive compounds.
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Phytotoxicity Study of (Amino)imidazo[1,2-]pyridine Derivatives Toward the Control of , , and Weeds.
J Agric Food Chem
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Instituto de Química, Laboratório de Química Metodológica e Orgânica Sintética (LaQMOS), Universidade de Brasília, 70904-970 Brasília, DF, Brazil.
In this work, several imidazo[1,2-]pyridines were synthesized through the Groebke-Blackburn-Bienaymé three-component reaction (GBB-3CR), and their phytotoxicity was evaluated by the influence on the growth of wheat coleoptiles and three important agricultural seeds (, , and ) at test concentrations of 1000, 300, 100, 30, and 10 μM. A structure-activity relationship was established, showing the importance of halogen groups at the position of the attached aromatic ring and the presence of a cyclohexylamine group for greater activity. Post-modification of some GBB-3CR adducts was carried out, leading to imidazo[1,2-]pyridine-tetrazole hybrids, which were also evaluated in these bioassays.
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Centre of Excellence in Pharmaceutical Sciences (CEPS), Guru Gobind Singh Indraprastha University, New Delhi 110078, India. Electronic address:
Multicomponent reactions (MCRs) have significant relevance in the field of synthetic chemistry, and in recent times one of the MCR variants, named the Groebke-Blackburn-Bienaymé (GBB) reaction, has attracted massive attention for the synthesis of biologically important scaffolds. The present review elaborates on the chemical advancement reported for the GBB reaction with an emphasis on the role of various catalytic systems. Further, the role of the GBB reaction has been redefined as a standard protocol for the synthesis of an array of potential bioactive compounds.
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Departamento de Química, División de Ciencias Naturales y Exactas, Universidad de Guanajuato, Noria Alta S/N, Col. Noria Alta, Guanajuato, C.P. 36050, Gto., México.
Bis-heterocycles were synthesized via a consecutive one-pot process by a Groebke-Blackburn-Bienaymé reaction (GBB-3CR) followed by Copper-catalyzed Alkyne-Azide Cycloaddition (CuAAC) assisted by alternative sustainable energies (ASE) such as ultrasonic and mechanical. These efficient and convergent strategies allowed the in situ generation of complex azides functionalized with imidazo[1,2-a]pyridines (IMPs), which was used as a synthetic platform. The target molecules contain two privileged scaffolds in medicinal chemistry: IMPs and the heterocyclic bioisostere of trans-amide bond, the 1,4-disubstituted 1H-1,2,3-triazoles (1,4-DS-1,2,3-Ts).
View Article and Find Full Text PDFThe Groebke-Blackburn-Bienaymé reaction in its maturity: innovation and improvements since its 21st birthday (2019-2023).
Beilstein J Org Chem
August 2024
Dipartimento di Chimica e Chimica Industriale, Università degli Studi di Genova, Via Dodecaneso 31, 16146 Genova, Italy.
The Groebke-Blackburn-Bienaymé (GBB) three-component reaction, discovered in 1998, is a very efficient strategy to assemble imidazo[1,2-]-heterocycles starting from amidines, aldehydes and isocyanides. This review aims to exhaustively describe innovative aspects of this reaction achieved during the last five years, and classifies them into five categories: synthetic methods, building blocks, scaffolds, biological activities and physical properties.
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ACS Omega
July 2024
Department of Chemistry and Centre for Advanced Studies, Panjab University, Chandigarh 160 014, India.
The Groebke-Blackburn-Bienaymé (GBB) reaction is a well-established three-component reaction for synthesizing imidazofused scaffolds from heterocyclic amidines, aldehydes, and isonitriles. However, the replacement of pyridoxal as an aldehyde component in this reaction results in the formation of the furo[2,3-]pyridine skeleton as an "unusual GBB product". Despite the interesting nature of this unusual reaction, not much work was further reported.
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