Synergistic Approach for Decarboxylative <i>Ortho</i> C−H Aroylation of 2‐Aryl‐pyrido[1,2‐a]pyrimidin‐4‐ones and Thiazolopyrimidinones by Merging Palladium Catalysis with Photocatalysis

Bhawale, Rajesh T.; Sarothiya, Durgesh; Kshirsagar, Umesh A.

doi:10.1002/ajoc.202200134

Cited by 4 publications

(1 citation statement)

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“…In 2022 , Our group developed a dual catalytic synergistic approach for decarboxylative ortho C‐H aroylation of 2‐aryl‐pyrido[1,2‐ a ]pyrimidin‐4‐ones 30 (Scheme 32) [48]. O 2 was used as very green oxidant under blue LED irradiation at room temperature to give 93 with a broad substrate scope and excellent yields up to 91%.…”

Section: Functionalization Of 4h‐pyrido[12‐a]pyrimidin‐4‐onementioning

confidence: 99%

4H‐Pyrido[1,2‐a]pyrimidin‐4‐one, biologically important fused heterocyclic scaffold: Synthesis and functionalization

Bhawale

Chillal

Kshirsagar

2023

Journal of Heterocyclic Chem

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4H‐pyrido[1,2‐a]pyrimidin‐4‐one and their derivatives are highly bioactive and multipurpose heterocyclic motifs, having application in drugs, natural products, agrochemical, material science, and organic synthesis. The C‐H functionalization of basic core structure of heterocycles have become indispensable tools that have continually increased the importance in the pharmaceutical industry for the synthesis of various useful heterocyclic molecules and their derivatives. In this review, we have provided a summary of various routes to synthesize 4H‐pyrido[1,2‐a]pyrimidin‐4‐one derivatives along with various derivatization methods such as via cross‐coupling, C‐H functionalization through arylation, alkenylation, sulfenylation, selenylation, phosphonation etc. taking into account the synthetic potentiality and significant influence of this scaffold in drug discovery.

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Section: Functionalization Of 4h‐pyrido[12‐a]pyrimidin‐4‐onementioning

confidence: 99%

4H‐Pyrido[1,2‐a]pyrimidin‐4‐one, biologically important fused heterocyclic scaffold: Synthesis and functionalization

Bhawale

Chillal

Kshirsagar

2023

Journal of Heterocyclic Chem

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Visible‐Light Induced Ag‐Palladacycle‐Complex‐Mediated Regioselective C−H Arylation

Bhawale,

Chillal,

Ghosh

et al. 2024

Adv Synth Catal

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A visible‐light‐induced, external photocatalyst‐free, site‐selective C‐H arylation of 4H‐pyrido[1,2‐a]pyrimidin‐4‐ones and various 2‐aryl heteroarenes has been developed to provide ortho arylated products 41‐ 95% yield at room temperature. A mechanistic study using controlled experiments, UV‐visible study, DFT study, and observation of colored aggregates suggest that in situ generated Ag‐palladacycle complex of 2‐aryl heteroarenes is responsible for absorbing the visible light and generating aryl radicals from aryldiazonium salts. Further, this methodology demonstrates its versatility by transforming various 2‐aryl heteroarenes, including 2‐phenylquinazolin‐4(3H)‐one, 3‐phenylquinoxalin‐2(1H)‐one, 2‐phenylpyridines, pyrazolo[1,5‐a]pyrimidines, 2‐phenylquinolines, 2‐phenylisoquinolines, and 2‐phenylbenzo[d]thiazoles, into their respective regio‐selective C‐H arylated products under mild reaction conditions.

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Visible‐Light‐Enabled Regioselective C−H alkylation and alkenylation of 2‐Aryl Heterocycles using Dual Catalysis

Bhawale,

Chillal,

Kshirsagar

2024

Adv Synth Catal

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Visible light‐induced site‐selective C−H alkylation and alkenylation of 2‐aryl heteroarenes with maleimides at room temperature via dual catalysis in an aqueous medium has been disclosed. This operationally simple and mild approach enables the selective formation of alkylation and alkenylation products up to 92% yield under silver‐free conditions with excellent substrate scope. For the mechanistic examination, KIE, H/D labeling experiments, light on‐off experiments, and quantum yield measurements were carried out. Moreover, the present approach for the alkylation and alkenylation of 2‐aryl heteroarenes is suitable for scalable synthesis.

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Synergistic Approach for Decarboxylative Ortho C−H Aroylation of 2‐Aryl‐pyrido[1,2‐a]pyrimidin‐4‐ones and Thiazolopyrimidinones by Merging Palladium Catalysis with Photocatalysis

Abstract: A mild and efficient synergistic approach for decarboxylative aroylation of 2-aryl-pyrido[1,2-a]pyrimidin-4ones having intrinsic directing group has been developed by merging of palladium catalysis and photoredox catalysis at [a] R.

Cited by 4 publications

References 61 publications

4H‐Pyrido[1,2‐a]pyrimidin‐4‐one, biologically important fused heterocyclic scaffold: Synthesis and functionalization

4H‐Pyrido[1,2‐a]pyrimidin‐4‐one, biologically important fused heterocyclic scaffold: Synthesis and functionalization

Visible‐Light Induced Ag‐Palladacycle‐Complex‐Mediated Regioselective C−H Arylation

Visible‐Light‐Enabled Regioselective C−H alkylation and alkenylation of 2‐Aryl Heterocycles using Dual Catalysis

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