A practical and cost-effective approach to polysubstituted pyrimidine derivatives<i>via</i>DBU mediated redox isomerization of propargyl alcohol and subsequent N–C–N fragment condensation

De, Rimpa; Sengupta, Utsav; Savarimuthu, Antony; Misra, Souvik; Nanda, Jayanta; Bera, Mrinal K.

doi:10.1039/d2nj00586g

Cited by 5 publications

(1 citation statement)

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“…Other Gold catalysts, IPrAuNTf In 2022, the research group of Bera, disclosed a straightforward synthesis of 2,4,6-trisubstituted pyrimidine derivatives 1 using sec-propargylic alcohols 4 and amidines 5 under basic conditions such as DBU (1,8-diazabicyclo[5.4.0]undec-7-ene). [23] They also employed guanidine hydrochloride as another N-C-N reacting partner to synthesize the corresponding 4,6-diaryl-2aminopyrimidine derivatives 3 (Scheme 14).…”

Section: Reactions Between Propargylic Alcohols and Amidines/guanidin...mentioning

confidence: 99%

Synthesis of Functionalized Pyrimidines from Propargylic alcohols and their Derivatives: Two Decades of Developments

Mishra,

Raikwar,

Baire

2023

Chemistry An Asian Journal

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Pyrimidine is a six-membered diaza-heterocycle i. e., 1,3-diazine. It is found to be present in many biologically and pharmacologically active scaffolds like nucleotides, natural products, and drugs. The bioactivities of pyrimidine include anti-tubercular, anti-bacterial, anti-fungal, anti-viral, anti-inflammatory, anti-malarial, anti-cancer, anti-neoplastic and many more. In this review article we have summarized various synthetic approaches that involve the synthesis of these privileged building blocks by employing propargylic alcohols and their derivatives like propargylic esters and propargylic ynones as three carbon-components. Here, we have confined ourselves to the developments appeared during the period of 23 years i. e., 2000-2022.

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Section: Reactions Between Propargylic Alcohols and Amidines/guanidin...mentioning

confidence: 99%

Synthesis of Functionalized Pyrimidines from Propargylic alcohols and their Derivatives: Two Decades of Developments

Mishra,

Raikwar,

Baire

2023

Chemistry An Asian Journal

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Copper-catalyzed synthesis of (E)-2,4-diaryl-6-styrylpyrimidines from distyrylketones and benzamidines

Li,

Wang,

2024

Journal of Molecular Structure

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An Atom-Economic Method for 1,2,3-Triazole Derivatives via Oxidative [3 + 2] Cycloaddition Harnessing the Power of Electrochemical Oxidation and Click Chemistry

Bandyopadhyay,

Bhadra,

Pathak

et al. 2023

J. Org. Chem.

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An electrochemical method was developed to accomplish the reagentless synthesis of 4,5-disubstituted triazole derivatives employing secondary propargyl alcohol as C-3 synthon and sodium azide as cycloaddition counterpart. The reaction was conducted at room temperature in an undivided cell with a constant current using a pencil graphite (C) anode and stainless-steel cathode in a MeCN solvent system. The proposed reaction mechanism was convincingly established by carrying out a series of control experiments and further supported by electrochemical and density functional theory (DFT) studies.

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A practical and cost-effective approach to polysubstituted pyrimidine derivativesviaDBU mediated redox isomerization of propargyl alcohol and subsequent N–C–N fragment condensation

Abstract: A straightforward, efficient yet effortless approach for the synthesis of structurally important triarylated pyrimidine derivatives has been successfully developed using secondary propargyl alcohol and commercially available amidines under mild basic...

Cited by 5 publications

References 55 publications

Synthesis of Functionalized Pyrimidines from Propargylic alcohols and their Derivatives: Two Decades of Developments

Synthesis of Functionalized Pyrimidines from Propargylic alcohols and their Derivatives: Two Decades of Developments

Copper-catalyzed synthesis of (E)-2,4-diaryl-6-styrylpyrimidines from distyrylketones and benzamidines

An Atom-Economic Method for 1,2,3-Triazole Derivatives via Oxidative [3 + 2] Cycloaddition Harnessing the Power of Electrochemical Oxidation and Click Chemistry

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