A one-pot three-component reactions for the synthesis of fully substituted spiro indeno[1,2-b]quinoxaline derivatives

Soleimani, Ebrahim; Hariri, Mina; Saei, Parisa

doi:10.1016/j.crci.2013.04.007

Cited by 17 publications

(5 citation statements)

References 36 publications

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“…In continuation of our interest in the synthesis of heterocyclic [16][17][18][19] and pyrazolone compounds, 20,21 we report the development herein of the synthesis of 4,5-dihydropyrazolyl-2H-indenediones via an aldol condensation of ninhydrin 3 and 1H-pyrazol-5-ol 4 in ethanol at room temperature in high yield (Scheme 1). It should be noted that the pyrazolones 4 were available by the condensation of β-keto esters 1 and hydrazine 2 in ethanol for 5 min (Scheme 1).…”

Section: Resultsmentioning

confidence: 99%

Synthesis of 4,5-dihydropyrazolyl-2H-indenediones by Aldol Condensation of Ninhydrin with 1H-pyrazol-5-ol

Soleimani

Hariri

Rostamzadeh

et al. 2016

Journal of Chemical Research

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Section: Resultsmentioning

confidence: 99%

Synthesis of 4,5-dihydropyrazolyl-2H-indenediones by Aldol Condensation of Ninhydrin with 1H-pyrazol-5-ol

Soleimani

Hariri

Rostamzadeh

et al. 2016

Journal of Chemical Research

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“…A series of highly substituted indenoquinoxline fused spiropyranopyrazoles (56) was synthesized in good yields via one-pot threecomponent reactions of 11H-indeno[1,2-b]quinoxalin-11-one (1), pyrazolones (54d) and malononitrile (53) in the presence of a catalytic amount of sodium carbonate as catalyst in ethanol under refluxed conditions (Figure 21). [55] Under these conditions, reactions required 12 hours to complete. In 2017, Narale et al [56] also carried out the same three-component reactions using 100 mg of bleaching earth as a catalyst in ethanol under refluxed conditions (Figure 22).…”

Section: Synthesis Of Indenoquinoxline Fused Spiropyranopyrazolesmentioning

confidence: 99%

One‐Pot Three‐Component Synthesis of Biologically Promising Indenoquinoxaline Fused Spiroheterocycles Starting from 11H‐indeno[1,2‐b]quinoxalin‐11‐ones

Banerjee,

Sharma,

Kaur

et al. 2024

ChemistrySelect

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Heterocycles are very common in many naturally occurring bioactive compounds as well as in the commercially available drug molecules. Very recently spiroheterocycles have gained considerable attention due to their wide range of pharmacological applicability. Among many others, 11H‐indeno[1,2‐b]quinoxalin‐11‐one in recent time have gained significant attention as an important building block to prepare structurally diverse biologically promising spiroheterocycles under various reaction conditions. On the other hand, it was found that one‐pot three‐component reaction strategy plays an important role in the preparation of spiroheterocycles starting from 11H‐indeno[1,2‐b]quinoxalin‐11‐one as it has many advantages including high atom economy, operational simplicity, easy workup procedures, reduction of byproducts, energy and reaction step efficiency etc. In this review, we have discussed all the recent developments related to the one‐pot three‐component synthesis of biologically promising indenoquinoxaline fused spiroheterocycles starting from 11H‐indeno[1,2‐b]quinoxalin‐11‐ones under diverse reaction conditions.

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“…In a Michael addition reaction the enolate gives the intermediate, which then undergoes a Thorpe–Ziegler intramolecular cyclization and subsequently, a 1,3‐sigmatropic shift to spiro indeno[1,2‐ b ]quinoxalines (Scheme 51). [61] …”

Section: Fused Quinoxalines By Mcr and One‐pot Synthesesmentioning

confidence: 99%

Multicomponent and One‐pot Syntheses of Quinoxalines

Biesen

Müller

2021

Adv Synth Catal

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Quinoxalines represent bicyclic nitrogen‐containing heterocycles with a wide array of applications. They exhibit a multitude of biological activities relevant in medicinal chemistry as well as a plethora of luminescence properties. Quinoxaline syntheses exploit the whole raft of multicomponent syntheses from domino to sequential or consecutive reactions, harvesting well‐known synthetic concepts and reactions, such as Ugi‐reactions, but also leading to the development of novel reactions and sequences. Diversity‐oriented synthesis and transition metal catalyzed multicomponent reactions open efficient pathways to quinoxalines and quinoxaline‐containing moieties in a one‐pot fashion. This review outlines the underlying reaction‐based principles of multicomponent syntheses of quinoxalines and summarizes recent developments quinoxaline‐directed MCRs, illustrating their scopes.

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A one-pot three-component reactions for the synthesis of fully substituted spiro indeno[1,2-b]quinoxaline derivatives

Cited by 17 publications

References 36 publications

Synthesis of 4,5-dihydropyrazolyl-2H-indenediones by Aldol Condensation of Ninhydrin with 1H-pyrazol-5-ol

Synthesis of 4,5-dihydropyrazolyl-2H-indenediones by Aldol Condensation of Ninhydrin with 1H-pyrazol-5-ol

One‐Pot Three‐Component Synthesis of Biologically Promising Indenoquinoxaline Fused Spiroheterocycles Starting from 11H‐indeno[1,2‐b]quinoxalin‐11‐ones

Multicomponent and One‐pot Syntheses of Quinoxalines

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