Microwave‐Assisted Domino Heck Cyclization and Phosphorylation: Synthesis of Phosphorus Containing Heterocycles

Ramesh, Karu; Satyanarayana, Gedu

doi:10.1002/ejoc.201900510

Cited by 11 publications

(7 citation statements)

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“…In 2019, the same group developed Pd‐catalyzed intra‐ and intermolecular Heck cyclization followed by phosphorylation, respectively, to construct phosphorus‐containing heterocyclic compounds (dihydrobenzofurans) [96] . The formation of C−C and C−P bonds are facilitated in microwave irradiation in quick reaction times.…”

Section: Resultsmentioning

confidence: 99%

“…According to the plausible mechanism, the Pd In 2019, the same group developed Pd-catalyzed intra-and intermolecular Heck cyclization followed by phosphorylation, respectively, to construct phosphorus-containing heterocyclic compounds (dihydrobenzofurans). [96] The formation of CÀ C and CÀ P bonds are facilitated in microwave irradiation in quick reaction times. In this protocol, the o-iodophenyl allyl ethers 35 were treated with diphenylphosphine oxide 46 to yield the phosphorylated dihydrobenzofurans 47, as illustrated in Scheme 5.…”

Section: Synthesis Of Dihydrobenzofurans By Using Microwave Irradiationmentioning

confidence: 99%

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Recent Advances Towards the Synthesis of Dihydrobenzofurans and Dihydroisobenzofurans

et al. 2022

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The 2,3-dihydrobenzofuran heterocyclic systems are found in various biologically active natural and pharmaceutical products of biological relevance such as Phalarine, Rocaglamide, and Furaquinocin A. The interest in the study of 2,3-dihydrobenzofurans is constantly increasing because of their numerous biological properties such as anti-tumor, anticancer, anti-tubercular, and anti-malarial activities. Different methods have been established towards the synthesis of 2,3dihydrobenzofurans involved via intra-and inter-molecular reactions. Besides, the 1,3-dihydroisobenzofuran structure has been identified as a fundamental nucleus in many natural products, bioactive compounds, and functional molecules (e. g., Pestacin, Isopestacin, Citalopram, Xylarinol B, Matriisobenzofuran, Thunberginol F7-O-β-D-glucopyranoside). On the other hand, 1,3-disubstituted isobenzofurans are powerful structural motifs with a wide range of biological activities, like anti-inflammatory, anti-histaminic, and anti-HIV. In the last few years, a decent number of diligent synthetic approaches have been demonstrated toward synthesizing 1,3-disubstituted isobenzofurans. This review focuses on the effective synthetic routes developed to construct 2,3-dihydrobenzofurans and 1,3-dihydroisobenzofurans and their applications in recent years.

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Section: Resultsmentioning

confidence: 99%

Section: Synthesis Of Dihydrobenzofurans By Using Microwave Irradiationmentioning

confidence: 99%

Recent Advances Towards the Synthesis of Dihydrobenzofurans and Dihydroisobenzofurans

et al. 2022

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“…In 2019, Karu Ramesh [49] et al have reported the synthesis of phosphorous-containing heterocycles via microwave-assisted domino Pd-catalyzed intramolecular Heck cyclization followed by phosphorylation reaction (Scheme 18). The process intensified the formation of CÀ C and CÀ P bonds in short reaction times.…”

Section: Synthesis Of Indole/oxindole-based Heterocyclesmentioning

confidence: 99%

Recent Advances in Transition Metal‐Catalyzed Domino‐Cyclization Strategies for Functionalized Heterocyclic/Carbocyclic Compounds

et al. 2022

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The discovery of the Domino reaction offers a useful strategy to the scientific community. From the beginning, it has received much attention in numerous advances for organic synthesis. Especially, for the constructive cyclization via multiple C−C and C‐heteroatom bond formation, the Domino‐Heck coupling reaction has become an essential tool in organic chemistry. In the case of drug synthesis, different natural products and biologically relevant scaffolds are achieved by employing the Domino‐cyclization technique. Palladium or nickel‐based intramolecular coupling reactions have been associated with many developing methods which lead to important carbo or heterocyclic scaffolds. In this account, metal‐catalyzed intramolecular cyclization is an emerging tool to access several heterocyclic scaffolds such as coumarins, quinolines, piperidines, indoles spiro and fused polycyclic rings. In this review, we have attempted to highlight the recent advances in metal‐mediated Domino cyclization reaction over the past few years.

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“…In the same year, Satyanarayana and Ramesh reported a palladium-catalyzed aerobic oxidative coupling of ortho -(alkynyl)styrenes and allylic alcohols via a 6- endo -dig annulation to obtain polysubstituted naphthalenes (Scheme 23 ). 48 The optimum conditions for this intramolecular cycloaromatization involved the use of PdCl 2 in an open-air atmosphere. The plausible catalytic cycle begins with coordination of the Pd(II) species to the triple bond of the styrene substrate, with the resulting intermediate undergoing an intramolecular 6- endo -dig cyclization via formation of a carbocation intermediate and HX elimination to restore the aromaticity.…”

Section: Oxidative C–c and C–nu Couplingmentioning

confidence: 99%

Recent Advances in Palladium-Catalyzed Oxidative Couplings in the Synthesis/Functionalization of Cyclic Scaffolds Using Molecular Oxygen as the Sole Oxidant

Barboza¹,

Dantas²,

Costa³

et al. 2021

Synthesis

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Over the past years, Pd(II)-catalyzed oxidative couplings enabled the achievement of molecular scaffolds with high structural diversity via C−C, C-N and C-O bond-formation reactions. In contrast to the use of stoichiometric amounts of more common oxidants, such as metal salts (Cu and Ag) and benzoquinone derivatives, the use of molecular oxygen in the direct or indirect regeneration of Pd(II) species presents itself as a more viable alternative in terms of economy and sustainability. In this review, we describe recent advances on the development Pd-catalyzed oxidative cyclizations/functionalizations, where molecular oxygen plays a pivotal role as the sole stoichiometric oxidant. 1 Introduction 2 Oxidative C-C and C-Nu Coupling 2.1 Intramolecular Oxidative C-Nu Heterocyclization Reactions 2.1.1 C-H Activation 2.1.2 Wacker/aza-Wacker Type Cyclization 2.1.3 Tandem Wacker/aza-Wacker and Cyclization/Cross Coupling Reactions 2.2 Intermolecular Oxidative C-Nu Heterocoupling Reactions 2.3 Intramolecular Oxidative (C-C) Carbocyclization Reactions 2.4 Intermolecular Oxidative C-C Coupling Reactions 2.4.1 Cyclization Reactions 2.4.2 Cross-Coupling Reactions 2.4.3 Homo-Coupling Reactions 3 Aerobic Dehydrogenative Coupling/Functionalization 4 Oxidative C-H Functionalization 5 Summary

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Microwave‐Assisted Domino Heck Cyclization and Phosphorylation: Synthesis of Phosphorus Containing Heterocycles

Cited by 11 publications

References 64 publications

Recent Advances Towards the Synthesis of Dihydrobenzofurans and Dihydroisobenzofurans

Recent Advances Towards the Synthesis of Dihydrobenzofurans and Dihydroisobenzofurans

Recent Advances in Transition Metal‐Catalyzed Domino‐Cyclization Strategies for Functionalized Heterocyclic/Carbocyclic Compounds

Recent Advances in Palladium-Catalyzed Oxidative Couplings in the Synthesis/Functionalization of Cyclic Scaffolds Using Molecular Oxygen as the Sole Oxidant

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