Intermolecular Nucleophilic Addition of N‐Diaminophosphinoyl‐Protected α‐Carbanions Derived from Secondary Amines to Arynes: Synthesis of 1‐Aryl‐1,2,3,4‐tetrahydroisoquinolines

Singh, K.; Singh, Paramjit; Kaur, Manjot; Sharma, Enakshi K.

doi:10.1002/slct.201700051

Cited by 7 publications

(6 citation statements)

References 88 publications

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“…The strong, broad stretching band at 3200 cm −1 in the IR spectrum, indicates the presence of an O−H alcohol group stretching by an intermolecular bonded functional group on prepared CDs while the peak at 1390 cm −1 could be assigned to the O−H bending of the alcoholic groups [31] . Moreover, the adsorption bands at 1655 cm −1 and 1590 cm −1 correspond to the C=O vibrations and the C=C band respectively indicating the asymmetric stretching of aromatic rings, esters, amides or carboxylic groups, revealing the aromatization and decarboxylation reaction of the OPW during the hydrothermal process [32] …”

Section: Resultsmentioning

confidence: 95%

Voltammetric Sensor Based on Waste‐Derived Carbon Nanodots for Enhanced Detection of Nitrobenzene

et al. 2023

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Carbon dots (CDs) samples were synthesized from orange peel waste (OPW) via a simple and eco-friendly hydrothermal carbonization (HTC) and electrochemical (EC) bottom-up synthesis integrated approach. The comprehensive chemical-physical characterization of CDs samples, carried out by various techniques such as TEM, EDX, XRD, FT-IR, underlined their morphological and microstructural features. The CDs exhibited attractive electrochemical properties, and thus an electrochemical sensor by modifying a screen printed carbon electrode (CDs/SPCE) for the detection of nitrobenzene (NB) in water was developed. Electroanalytical performances of CDs/SPCE sensor using differential pulse voltammetry (DPV) demonstrated its high sensitivity (9.36 μA μM À 1 cm À 2 ) towards NB in a wide linear dynamic range (0.1-2000 μM) and a low limit of detection (LOD = 13 nM). The electrochemical sensor also shown high selectivity, long-term stability, and repeatability. This paper might open the way to a new synergistic HTC-EC approach for the synthesis of CDs from waste biomass material and their advanced application in highly efficient electrochemical sensors.

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Section: Resultsmentioning

confidence: 95%

Voltammetric Sensor Based on Waste‐Derived Carbon Nanodots for Enhanced Detection of Nitrobenzene

et al. 2023

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“…However, regioselectivity of lithiation in cyclic tertiary amines can be altered by prior treatment of amine with Lewis acid i. e. BF 3 or BH 3 [16a] . Our research group has established a novel synthetic approach for arylation which involved a coupling reaction of amino carbanion with in situ generated benzyne to give α/β‐arylated cyclic amines [15a,c,d,e] …”

Section: Resultsmentioning

confidence: 99%

Intramolecular Nucleophilic Addition of N‐Boc Protected α‐Amino Carbanions to Arynes: Synthesis of 1‐Aryl‐2,3,4,5‐tetrahydro‐1H‐2‐benzazepines

Kaur

Sharma²,

Singh³

et al. 2022

ChemistrySelect

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A two-step protocol involving cyclization and deprotection towards the synthesis of C-1 arylated benzazepines has been developed under transition-metal oxidant free conditions. The coupling reaction of a-lithiated carbanion, generated from Boc-protected amine, with in situ generated aryne proceeds well intramolecularly. A variety of substrates were explored with corresponding products in moderate yield.

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“…Singh and his groups reported the synthesis of three different pyrimidine derivatives 600–602 using carbon quantum dots (CQD) as an efficient acid‐base bifunctional catalyst via MCR (Scheme 118). [137] …”

Section: Six‐membered Heterocyclic Compoundsmentioning

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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Intermolecular Nucleophilic Addition of N‐Diaminophosphinoyl‐Protected α‐Carbanions Derived from Secondary Amines to Arynes: Synthesis of 1‐Aryl‐1,2,3,4‐tetrahydroisoquinolines

Cited by 7 publications

References 88 publications

Voltammetric Sensor Based on Waste‐Derived Carbon Nanodots for Enhanced Detection of Nitrobenzene

Voltammetric Sensor Based on Waste‐Derived Carbon Nanodots for Enhanced Detection of Nitrobenzene

Intramolecular Nucleophilic Addition of N‐Boc Protected α‐Amino Carbanions to Arynes: Synthesis of 1‐Aryl‐2,3,4,5‐tetrahydro‐1H‐2‐benzazepines

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

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