One-Pot Synthesis of Quinoline-Based Tetracycles by a Tandem Three-Component Reaction

Che, Chao; Xiang, Jing; Wang, Guoxin; Fathi, Reza; Quan, Jing; Yang, Zhen

doi:10.1021/cc070058a

Cited by 60 publications

(34 citation statements)

References 29 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Furthermore, diverse catalysts were reported to accelerate the reaction. This included Brønsted acids, such as acetic acid [16], perchloric acid [14][15][16], tosylic acid [54], silicasulfuric acid [55], NH 4 Cl [50,56], clay (montmorillonite K-10) [57] and PTSA/N -hydroxysuccinimide [58]. Additionally, several Lewis acids were used, such as Sc(OTf) 3 [14][15][16], MgCl 2 [59], InCl 3 [60], ZnCl 2 [61], RuCl 3 [62], tin(II) chloride dehydrate [63], trimethylsilyl chloride (TMSCl) [65] and Yb(OTf) 3 [66].…”

Section: Variations Of the Catalyst And Solventmentioning

confidence: 99%

Groebke–Blackburn–Bienaymé multicomponent reaction: emerging chemistry for drug discovery

2015

View full text Add to dashboard Cite

The Groebke-Blackburn-Bienaymé reaction (GBBR) is used for the one-pot synthesis of therapeutically relevant fused imidazoles bridgehead nitrogen heterocyclic compounds from readily available aldehyde, isocyanide and amidine building blocks. The reaction is driven by a wide range of catalysts and can be performed either under solvent or solvent-free conditions, or under microwave irradiation as heat source. The GBBR products can be used for the synthesis of a variety of more complex scaffolds via postmodification reactions. These include cyclization and nucleophilic substitution as well as further MCRs. The GBBR reaction has seen diverse applications in combinatorial and medicinal chemistry and its products are of great use in drug discovery. In this review, we summarize the efforts of the chemistry community in the progress and applications of GBBR since 1998. This review also includes some biological profiles and synthetic scopes of GBBR products. The component variations, postmodifications and secondary transformations will also be discussed throughout this review.

show abstract

Section: Variations Of the Catalyst And Solventmentioning

confidence: 99%

Groebke–Blackburn–Bienaymé multicomponent reaction: emerging chemistry for drug discovery

2015

View full text Add to dashboard Cite

show abstract

“…They mostly involve different substituted 3-amino-1,2,4-triazoles [71–75] and 2-amino(benzo)thiazoles [71–72 76–88]. Several publications deal with 2-amino-1,3,4-thiadiazoles [71,83–84 89–90], 2-aminoimidazoles [71–72 91–92], 2-aminoxazoles [71] and 1,2,5-oxadiazole-3,4-diamine [93] with the formation of imidazoazoles. Among the pyrazoles only 5-amino-3-methylpyrazole, 5-aminopyrazole-4-carbonitrile and ethyl 5-aminopyrazole-4-carboxylate are described in GBB-3CR [29,71,83–84 94–96].…”

Section: Introductionmentioning

confidence: 99%

New tricks of well-known aminoazoles in isocyanide-based multicomponent reactions and antibacterial activity of the compounds synthesized

Murlykina

Kornet

Десенко

et al. 2017

Beilstein J. Org. Chem.

View full text Add to dashboard Cite

The well-known aminoazoles, 3-amino-5-methylisoxazole and 5-amino-N-aryl-1H-pyrazole-4-carboxamides, were studied as an amine component in Ugi and Groebke–Blackburn–Bienaymé multicomponent reactions. The first example of an application of aminoazoles in an Ugi four-component reaction was discovered and novel features of a Groebke–Blackburn–Bienaymé cyclocondensation are established and discussed. The heterocycles obtained were evaluated for their antibacterial activity and several of them demonstrated a weak antimicrobial effect, but for most of the compounds a 30–50% increase in biomass of Gram-positive strains (mainly B. subtilis) compared to control was observed.

show abstract

“…In continuation of our research on the development of MCR strategies for the rapid library synthesis of biologically interesting heterocycles [43–47], we were interested in a practical synthetic strategy towards imidazo[1,2- a ]pyridine-fused isoquinoline systems. We believe that this type of polycyclic systems may have interesting biological profiles [48].…”

Section: Introductionmentioning

confidence: 99%

A practical and efficient approach to imidazo[1,2-a]pyridine-fused isoquinolines through the post-GBB transformation strategy

Shao¹,

Gong²,

Su³

et al. 2017

Beilstein J. Org. Chem.

Self Cite

View full text Add to dashboard Cite

Diversity-oriented synthesis of the biologically intriguing imidazo[1,2-a]pyridine-fused isoquinoline systems from readily available starting materials was achieved through the Groebke–Blackburn–Bienaymé reaction followed by a gold-catalyzed cyclization strategy. The synthetic approach is characterized by mild reaction conditions and a broad substrate scope, allowing for the rapid construction of structurally complex and diverse heterocycles in moderate to good yields.

show abstract

One-Pot Synthesis of Quinoline-Based Tetracycles by a Tandem Three-Component Reaction

Cited by 60 publications

References 29 publications

Groebke–Blackburn–Bienaymé multicomponent reaction: emerging chemistry for drug discovery

Groebke–Blackburn–Bienaymé multicomponent reaction: emerging chemistry for drug discovery

New tricks of well-known aminoazoles in isocyanide-based multicomponent reactions and antibacterial activity of the compounds synthesized

A practical and efficient approach to imidazo[1,2-a]pyridine-fused isoquinolines through the post-GBB transformation strategy

Contact Info

Product

Resources

About