Novel Double [3 + 2 + 1] Heteroannulation for Forming Unprecedented Dipyrazolo-Fused 2,6-Naphthyridines

Fan, Wei; Ye, Qin; Xu, Haiwei; Jiang, Bo; Wang, Shuliang; Tu, Shu‐Jiang

doi:10.1021/ol4008266

Cited by 63 publications

(9 citation statements)

References 45 publications

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“…Thus, depending on the substituent in the phenyl ring of aniline, two different products were obtained. The same authors also reported a four‐component reaction of phenylglyoxal and 7 , with which dipyrazolo‐fused 2,6‐naphthyridines could be obtained through a double [3+2+1] heteroannulation reaction by using n ‐butyric acid as a catalyst …”

Section: Aliphatic Axb3 Smentioning

confidence: 97%

Aldo‐X Bifunctional Building Blocks for the Synthesis of Heterocycles

Ravichandiran

Lai

2016

The Chemical Record

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Compounds containing oxygen, nitrogen, or sulfur atoms inside the rings are attracting much attention and interest due to their biological importance. In recent years, several methods for the synthesis of such molecules have been reported by using aldo-X bifunctional building blocks (AXB3 s) as substrates; these are a wide class of organic molecules that contain at least two reactive sites, among them, one aldehyde, acetal, or semiacetal group was involved. Because of the multiple reactivities, AXB3 s are widely used in the one-pot synthesis of biologically important heterocycles. This review summarizes the synthesis of important heterocycles by using AXB3 s as pivotal components in establishing multicomponent reactions, tandem reactions, and so forth. In many cases, the established reaction systems with AXB3 s were characterized by some green properties, such as easy access to the substrate, mild and environmentally benign conditions, and wide scope of the substrate.

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Section: Aliphatic Axb3 Smentioning

confidence: 97%

Aldo‐X Bifunctional Building Blocks for the Synthesis of Heterocycles

Ravichandiran

Lai

2016

The Chemical Record

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“…[22] On this basis, diverse nitrogencontaining heterocyclic compounds were constructed by using 5-aminopyrrole as the starting material including bicyclic, tricyclic, tetracyclic, and spiro-fused pyrazole derivatives. [23][24][25][26][27] However, the reaction of introducing ar-ylthio group on 5-aminopyrrole to synthesize unsymmetrical diaryl sulfide has rarely been reported. Numerous studies have shown that the introduction of sulfur-containing groups increased biological activity of functional molecules.…”

Section: Introductionmentioning

confidence: 99%

One-Pot Two-Step Strategy for Efficient Synthesis of 3-Aryl-4-(arylthio)-1H-pyrazol-5-amines Derivatives

Feng¹,

He²,

Wei³

et al. 2022

Chinese Journal of Organic Chemistry

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One-pot two-step reaction of 3-oxo-3-arylpropanenitriles, methyl hydrazinecarboxylate (or hydrazine hydrate), and arylsulfonyl hydrazides has been established, and a series of 3-aryl-4-(arylthio)-1H-pyrazol-5-amines were constructed by sequential cyclization, sulfenylation, and removal of COOMe group under the action of I2 and N-iodo-succininide (NIS), respectively. The method represents good atomic economy, mild reaction conditions, broad substrate scope, and gram-scale synthesis. Moreover, the further transformations of 3-aryl-4-(arylthio)-1H-pyrazol-5-amine products were also investigated.

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“…In special, 5-amino-1 H -pyrazoles are valuable compounds that present several biological and pharmaceutical activities including antiviral, anticancer, antituberculosis, anti-inflammatory, antifungal and antidepressive activity [14–17]. Moreover, they have been extensively used as synthons to prepare a wide variety of fused N-heterocycles of synthetic and pharmacological importance [18–20]. Thus, an effective strategy for the design and the preparation of new pharmacologically promising drugs that combine at least two bioactive moieties in one molecule avoiding residual metal in transition-metal catalysis in environmental benign conditions is desired.…”

Section: Introductionmentioning

confidence: 99%

Molecular iodine-catalyzed one-pot multicomponent synthesis of 5-amino-4-(arylselanyl)-1H-pyrazoles

Pires¹,

Hartwig²,

Pontel³

et al. 2018

Beilstein J. Org. Chem.

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A one-pot iodine-catalyzed multicomponent reaction has been developed for the selective preparation of 5-amino-4-(arylselanyl)-1H-pyrazoles from a diverse array of benzoylacetonitriles, arylhydrazines and diaryl diselenides. The reactions were conducted in MeCN as solvent at reflux temperature under air. The methodology presents a large functional group tolerance to electron-deficient, electron-rich, and bulky substituents and gave the expected products in good to excellent yields. The synthesized 1,3-diphenyl-4-(phenylselanyl)-1H-pyrazol-5-amine was submitted to an oxidative dehydrogenative coupling to produce a diazo compound confirmed by X-ray analysis.

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Novel Double [3 + 2 + 1] Heteroannulation for Forming Unprecedented Dipyrazolo-Fused 2,6-Naphthyridines

Cited by 63 publications

References 45 publications

Aldo‐X Bifunctional Building Blocks for the Synthesis of Heterocycles

Aldo‐X Bifunctional Building Blocks for the Synthesis of Heterocycles

One-Pot Two-Step Strategy for Efficient Synthesis of 3-Aryl-4-(arylthio)-1H-pyrazol-5-amines Derivatives

Molecular iodine-catalyzed one-pot multicomponent synthesis of 5-amino-4-(arylselanyl)-1H-pyrazoles

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