Photocyclization of coumarinoyl enamides revisited: [2+2+2] cycloreversion/cycloaddition mechanism

Chithanna, Sivanna; Yang, Ding‐Yah

doi:10.1039/d1nj00352f

Cited by 3 publications

(1 citation statement)

References 42 publications

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“…Pechmann dyes ( C and D ) exhibit different colors and have significant applications in optoelectronic materials . Owing to the relevance of these compounds in various fields, complicated multistep procedures were developed for their synthesis from expensive starting materials that were not readily available . Currently, C–H activation and functionalization provide ample opportunities to synthesize these structurally complex molecules via short synthetic routes from simple and readily available starting materials.…”

Section: Introductionmentioning

confidence: 99%

Rh(III)-Catalyzed Dual C–H Functionalization and C–O/C–N Annulations of Monoamide Fumarates

et al. 2022

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Pyrano[4,3-c]pyridine-diones, which are the key skeleton of bioactive compounds and functional materials, are usually prepared via a multistep synthesis using expensive substrates. This work demonstrates that Rh(III)-catalyzed dual C(sp2)–H functionalization and C–O/C–N annulation of monoamide fumarates can produce pyrano[4,3-c]pyridine-1,5(6H)-diones in high yield (up to 82%) in a single step. The substrates of monoamide fumarates and acetylenes are structurally simple, readily available, and inexpensive. The additive AgSbF6 effectively raised the yields. On account of easier dehydrogenation of OH in the COOH group than NH in the amide group in the reaction, the process first undergoes C–O annulation and then is succeeded by C–N annulation.

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Section: Introductionmentioning

confidence: 99%

Rh(III)-Catalyzed Dual C–H Functionalization and C–O/C–N Annulations of Monoamide Fumarates

et al. 2022

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Recent advances on the synthesis of pyrido[3,4-c]coumarin derivatives as the backbone of natural product schumanniophytin scaffolds

Samanta,

Patra,

Biswas

et al. 2024

Monatsh Chem

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One-Pot Synthesis of Chromone-Fused Pyrrolo[2,1-a]isoquinolines and Indolizino[8,7-b]indoles: Iodine-Promoted Oxidative [2 + 2 + 1] Annulation of O-Acetylphenoxyacrylates with Tetrahydroisoquinolines and Noreleagnines

Shang

Zhang

et al. 2021

J. Org. Chem.

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An iodine-promoted one-pot cascade oxidative annulation reaction has been developed for the synthesis of chromone-fused-pyrrolo[2,1-a]isoquinolines and indolizino[8,7-b]indoles from o-acetylphenoxyacrylates, tetrahydroisoquinolines, and noreleagnines. This process underwent a logical approach to both chromone-fused-pyrrolo[2,1-a]isoquinolines and chromone-fused-indolizino[8,7-b]indoles isolamellarin derivatives. Manipulations of l-menthol and dl-α-tocopherol demonstrate the applications of this strategy.

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Photocyclization of coumarinoyl enamides revisited: [2+2+2] cycloreversion/cycloaddition mechanism

Abstract: The major and minor products for photocyclization of coumarinoyl enamides were identified. The controlled and intermediate-trapping experiments indicate that the formation of the minor isomer involved a stepwise, radical [2+2+2]...

Cited by 3 publications

References 42 publications

Rh(III)-Catalyzed Dual C–H Functionalization and C–O/C–N Annulations of Monoamide Fumarates

Rh(III)-Catalyzed Dual C–H Functionalization and C–O/C–N Annulations of Monoamide Fumarates

Recent advances on the synthesis of pyrido[3,4-c]coumarin derivatives as the backbone of natural product schumanniophytin scaffolds

One-Pot Synthesis of Chromone-Fused Pyrrolo[2,1-a]isoquinolines and Indolizino[8,7-b]indoles: Iodine-Promoted Oxidative [2 + 2 + 1] Annulation of O-Acetylphenoxyacrylates with Tetrahydroisoquinolines and Noreleagnines

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