Aqueous hydrotropic solution: green reaction medium for synthesis of pyridopyrimidine carbonitrile and spiro-oxindole dihydroquinazolinone derivatives

Patil, Audumbar; Mane, Ananda; Kamat, Siddharth; Lohar, Trushant; Salunkhe, Rajashri

doi:10.1007/s11164-019-03801-8

Cited by 22 publications

(4 citation statements)

References 47 publications

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“…A chloro-substituted substrate gave the corresponding dihydroquinazolinone 3 y with a 71 % yield. Among the spiro-dihydoquinazolinones (Scheme 2), compound 3 r has been reported to have chorismate mutase inhibitory activity, [19] and derivatives of compound 3 p have IRAP inhibitory activity. [20] Table 1.…”

Section: Chemistryselectmentioning

confidence: 99%

Access to Dihydroquinazolinones, spiro‐Quinazolinones and their Bioactive Molecular Scaffolds by Exploring the Unique Reactivity of 2‐Nitrobenzonitrile towards Cu‐Hydrazine Hydrate

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Pal

2023

ChemistrySelect

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A unique reactivity of 2‐nitrobenzonitrile towards hydrazine hydrate has been demonstrated, which was explored for the rapid and efficient synthesis of dihydro‐quinazolinone derivatives. In this reaction, hydrolysis of nitriles followed by reduction of the nitro group was observed only for the ortho‐isomer. The reaction sequences involve a concerted pathway for the formation of 2‐aminobenzamide from 2‐nitrobenzonitrile, where copper catalyzed both the hydrolysis of the cyano group as well as the reduction of the nitro group simultaneously. This methodology has been used to synthesize a variety of electronically varied spiro‐ and dihydro quinazolinones with high yield and functional group tolerance. In addition, the methodology has also been applied to the synthesis of biologically potent molecular entities.

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Section: Chemistryselectmentioning

confidence: 99%

Access to Dihydroquinazolinones, spiro‐Quinazolinones and their Bioactive Molecular Scaffolds by Exploring the Unique Reactivity of 2‐Nitrobenzonitrile towards Cu‐Hydrazine Hydrate

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2023

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“…explored the application of 50 % aqueous sodium p ‐toluene sulfonate (NaPTS) as an aqueous hydrotropic solution to promote the 3‐MCR between isatin, anilines and isatoic anhydride (Scheme 66). The resulting spirooxindole‐dihydroquinazolinone derivatives (14 examples) were obtained in very good yields, with the advantage that the reaction media could be recovered and reused directly in the next run, without significant loss of activity [132] …”

Section: Spirooxindole Derivativesmentioning

confidence: 99%

“…trisodium citrate dehydrate [60] Borax [68] SDS [108] sodium p ‐toluene sulfonate [132] TBAB [133] KAl(SO 4 ) 2 .12H 2 O [183] …”

Section: Spirooxindole Derivativesmentioning

confidence: 99%

Engaging Isatins in Multicomponent Reactions (MCRs) – Easy Access to Structural Diversity

Brandão

Marques

Carreiro

et al. 2021

The Chemical Record

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Multicomponent reactions (MCRs) are a valuable tool in diversity‐oriented synthesis. Its application to privileged structures is gaining relevance in the fields of organic and medicinal chemistry. Isatin, due to its unique reactivity, can undergo different MCRs, affording multiple interesting scaffolds, namely oxindole‐derivatives (including spirooxindoles, bis‐oxindoles and 3,3‐disubstituted oxindoles) and even, under certain conditions, ring‐opening reactions occur that leads to other heterocyclic compounds. Over the past few years, new methodologies have been described for the application of this important and easily available starting material in MCRs. In this review, we explore these novelties, displaying them according to the structure of the final products obtained.

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“…Therefore, the improvement of a new, efficient and environment‐friendly procedure is essential, which tolerate the synthesis of heterocycles containing phthalazine ring fragment. Knowing the chemical and pharmacological importance, the chromeno pyrazolo and indazolo phthalazine derivatives and as a part of our continuing efforts towards the development of sustainable routes for the preparation of biologically active compounds, herein, we have reported an efficient multicomponent synthesis of phthalazine derivatives in DES.…”

Section: Introductionmentioning

confidence: 99%

Deep eutectic solvent an efficient reaction medium for the synthesis of chromeno pyrazolo and indazolo phthalazine derivatives

Patil

Lohar

Mane

et al. 2019

Journal of Heterocyclic Chem

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The volatile, harmful and hazardous solvents have impact on human health, all organisms and environment. To reduce the use of hazardous volatile solvents, there is need to develop the alternative green reaction medium for organic transformations and is the main goal of green chemistry. The green solvent should be nonvolatile, nontoxic, biodegradable and biorenewable. Considering these parameters, herein, we have reported an efficient and environmentally benign green synthesis of chromeno pyrazolo and indazolo phthalazine derivatives in deep eutectic solvent. The present protocol contains excellent yield of the product, short reaction time, operation simplicity, reusability of solvent and no need of further purification.

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Aqueous hydrotropic solution: green reaction medium for synthesis of pyridopyrimidine carbonitrile and spiro-oxindole dihydroquinazolinone derivatives

Cited by 22 publications

References 47 publications

Access to Dihydroquinazolinones, spiro‐Quinazolinones and their Bioactive Molecular Scaffolds by Exploring the Unique Reactivity of 2‐Nitrobenzonitrile towards Cu‐Hydrazine Hydrate

Access to Dihydroquinazolinones, spiro‐Quinazolinones and their Bioactive Molecular Scaffolds by Exploring the Unique Reactivity of 2‐Nitrobenzonitrile towards Cu‐Hydrazine Hydrate

Engaging Isatins in Multicomponent Reactions (MCRs) – Easy Access to Structural Diversity

Deep eutectic solvent an efficient reaction medium for the synthesis of chromeno pyrazolo and indazolo phthalazine derivatives

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