A Metal Free, Hantzsch Synthesis for Privileged Scaffold 1, 4-Dihydropyridines: A Glycerol Promoted Sustainable Protocol

Tiwari, Saurabh; Shivhare, Km Neha; Patel, Manoj K.; Yadav, Vikas; Nazeef, Mohd; Siddiqui, I. R.

doi:10.1080/10406638.2020.1764988

Cited by 9 publications

(8 citation statements)

References 42 publications

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“…The reaction occurs via Knoevenagel condensation of the aldehyde 1 and malononitrile with elimination of water derivatives 512-513 via one pot multicomponent Hantzsch reaction using benzaldehyde 1, two moles of dimedone and ammonium acetate or aniline 3 in glycerol as promoting media at 65 °C (Scheme 97). [116] The glycerol used in this reaction is a nontoxic and inexpensive by-product of the biodiesel industry and it has been proposed that glycerol has a favorable ability to promote chemical reactions, acting as both a solvent to dissolve the substrate molecules and an activator of electrophilic substrate molecules due to its strong hydrogen bonding capabilities. At first, glycerol enolized the dimedone as well as activares the aryl aldehyde 1 through hydrogen bonding.…”

Section: Synthesis Of Pyridines and Quinolinesmentioning

confidence: 99%

Transition‐Metal‐Free Synthesis of N‐Heterocyclic Compounds via Multi‐Component Reactions

et al. 2023

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Multicomponent reactions (MCRs) have emerged as powerful tools in synthetic chemistry for the efficient synthesis of diverse molecular scaffolds, particularly nitrogen‐containing heterocycles. Despite their numerous advantages, the use of transition metal catalysts or additives in MCRs can present limitations due to cost, toxicity, and environmental concerns. In recent years, there has been a growing interest in transition metal‐free MCRs for the synthesis of N‐heterocyclic compounds. This review provides a comprehensive and concise overview of the recent advancements in transition metal‐free MCRs for the synthesis of valuable N‐heterocycles over the past five years. The review is systematically organized, categorizing the discussed MCRs based on the size of the heterocyclic ring and the number of nitrogen atoms. Only MCRs that result in the formation of heterocyclic rings containing at least one nitrogen atom are included, while the derivatization of N‐heterocycles using transition metal‐free MCRs falls outside the scope of this review. By highlighting the recent developments in this field, this review aims to showcase the potential and significance of transition metal‐free MCRs as sustainable and efficient strategies for accessing N‐heterocyclic compounds. The elimination of transition metals not only simplifies the reaction conditions but also contributes to greener and more environmentally friendly synthetic approaches. This review serves as a valuable resource for researchers interested in the design and application of transition metal‐free MCRs in the synthesis of nitrogen‐containing heterocycles.

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Section: Synthesis Of Pyridines and Quinolinesmentioning

confidence: 99%

Transition‐Metal‐Free Synthesis of N‐Heterocyclic Compounds via Multi‐Component Reactions

et al. 2023

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“…[187][188][189] In 2020, a metal-free method has developed where glycerol (the low-cost side product of biodiesel industries) used as a solvent and catalyst at 65 °C for acridine-1,8dione derivatives 36&37 synthesis with good to excellent yield (Scheme 31). [68] In the same year, a similar reaction reported utilizing glycerol as solvent and catalyst but the reaction was carried out at room temperature. [190] Few other similar reports published in literature for the synthesis of acridinedione derivatives 38 from the reaction of dimedone, benzaldehyde and ammonium acetate under different catalytic and non-catalytic conditions which are summarised in Table 2 4.…”

Section: Synthesis Of Acridine-18-dione Derivativesmentioning

confidence: 99%

“…Glycerol promoted synthesis of acridine-1,8-dione derivatives. [68] In 2016, our group synthesized N-substituted 4,4a,5,6tetrahydroquinoline-2,7(1H,3H)-diones 42 starting from 4-substituted cyclohexane-1,3-diones which were earlier synthesized from acetone and ethyl acrylate under basic reaction conditions. [91] The desired product was prepared in three steps using protection, amidation, and deprotective-cyclization processes.…”

Section: Synthesis Of Acridine-18-dione Derivativesmentioning

confidence: 99%

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Application of Cyclohexane‐1,3‐diones in the Synthesis of Six‐Membered Nitrogen‐Containing Heterocycles

Sharma¹,

Kumar

et al. 2022

ChemistrySelect

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Cyclohexane‐1,3‐dione and its derivatives are imperative precursors in synthetic organic chemistry as they are useful intermediates for the synthesis of a wide range of biologically active natural products, heterocycles and pharmaceuticals. Recently, cyclohexane‐1,3‐diones have been used for the synthesis of varied array of six‐membered nitrogen‐containing heterocycles in the presence of aldehydes, acetoacetic esters, malononitrile, chalcones, coumarins, acetophenones, amino acids, amines, etc. under catalytic and non‐catalytic conditions. Newest studies on the importance of these heterocycles motivated us to compile all the recently developed processes which include the fabrication of six‐membered nitrogen heterocycles. This article is mainly focused on the efficient synthesis of six‐membered N‐heterocycles i. e. 1,4‐dihydropyridine, acridine‐1,8‐diones, benzoacridinones, quinolones and pyridine derivatives from cyclohexane‐1,3‐diones as one of the substrates, published for the last ten years.

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“…In continuation of our ongoing research program on the development of green synthetic routes to biologically significant heterocyclic compounds, [41][42][43][44] we herein report a new and efficient, operationally simple, catalyst free, glycerol promoted one-pot synthesis of benzo[a]chromeno[2,3-c]phenazines (Scheme 1). (Table 1, Entry 1).…”

Section: Introductionmentioning

confidence: 99%

Catalyst Free, Multicomponent Green Approach to Benzo[a]chromeno[2,3‐c]phenazines Using Glycerol as a Recyclable and Biodegradable Promoting Medium

et al. 2020

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A series of benzo[a]chromeno[2,3‐c]phenazine derivatives were synthesized through an efficient one‐pot, multicomponent eco‐friendly reaction of 2‐hydroxynaphthalene‐1,4‐dione, o‐phenylenediamines, cyclic 1,3‐dicarbonyl compounds and aromatic aldehydes, promoted by glycerol. To the best of our knowledge this is the first catalyst free protocol for synthesis of this important scaffold having potential applications in medicinal and materials chemistry. Other important attributes of the present method are the use of glycerol as a bio‐renewable and biodegradable reaction medium‐cum‐promoter, use of readily available substrates, mild reaction conditions, operational simplicity, broad substrate scope, short reaction time, easy workup, and high yields and atom efficiency, which makes the disclosed protocol a superior alternative to existing methods.

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A Metal Free, Hantzsch Synthesis for Privileged Scaffold 1, 4-Dihydropyridines: A Glycerol Promoted Sustainable Protocol

Cited by 9 publications

References 42 publications

Transition‐Metal‐Free Synthesis of N‐Heterocyclic Compounds via Multi‐Component Reactions

Transition‐Metal‐Free Synthesis of N‐Heterocyclic Compounds via Multi‐Component Reactions

Application of Cyclohexane‐1,3‐diones in the Synthesis of Six‐Membered Nitrogen‐Containing Heterocycles

Catalyst Free, Multicomponent Green Approach to Benzo[a]chromeno[2,3‐c]phenazines Using Glycerol as a Recyclable and Biodegradable Promoting Medium

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