Domino Hydroarylation–Cyclization Reaction: One‐Pot Synthesis of Indane‐Fused 3,4‐Dihydrocoumarins

Joo, Jin Hyuck; Youn, So Won

doi:10.1002/adsc.201200745

Cited by 9 publications

(2 citation statements)

References 65 publications

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“…Moreover, Youn and Joo have described the use of phenols as nucleophiles with o-(alkynyl)benzylidenemalonates for the synthesis of 3,4-dihydrocoumarin-fused 1-methyleneindanes by a tandem reaction catalyzed by Sn(OTf) 2 (Scheme 54). 146 The reaction is proposed to proceed by initial arylation of the activated electron-deficient olefin followed by intramolecular lactonization that furnishes the coumarin ring. Then, the indane skeleton is formed by intramolecular nucleophilic addition of a tin-enolate onto the alkyne, activated by the Lewis acid as well.…”

Section: -Methyleneindanesmentioning

confidence: 99%

“…146 The reaction is proposed to proceed by initial arylation of the activated electron-deficient olefin followed by intramolecular lactonization that furnishes the coumarin ring. Then, the indane skeleton is formed by intramolecular nucleophilic addition of a tin-enolate onto the alkyne, activated by the Lewis acid as well.…”

Section: Scheme 53 Synthesis Of 1-vinylidenindanes By Palladium-or Nmentioning

confidence: 99%

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1,3-Dien-5-ynes: Versatile Building Blocks for the Synthesis of Carbo- and Heterocycles

et al. 2016

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ABSTRACT:1,3-Dien-5-ynes have been extensively used as starting materials for the synthesis of a wide number of different carbo-and heterocycles. The aim of this review is to give an overview of their utility in organic synthesis, highlighting the variety of compounds that can be directly accessed from single reactions over these systems. Thus, cycloaromatization processes are initially commented, followed by reactions directed towards the syntheses of five-membered rings, other carbocycles and, finally, heterocycles. The diverse methodologies that have been developed for the synthesis of each of these types of compounds from 1,3-dien-5-ynes are presented, emphasizing the influence of the reaction conditions and the use of additional reagents in the outcome of the transformations.2

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Section: -Methyleneindanesmentioning

confidence: 99%

Section: Scheme 53 Synthesis Of 1-vinylidenindanes By Palladium-or Nmentioning

confidence: 99%

1,3-Dien-5-ynes: Versatile Building Blocks for the Synthesis of Carbo- and Heterocycles

et al. 2016

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ChemInform Abstract: Domino Hydroarylation—Cyclization Reaction: One‐Pot Synthesis of Indane‐Fused 3,4‐Dihydrocoumarins.

Joo

Youn

2013

ChemInform

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Radical‐Enabled Bicyclization Cascades of Oxygen‐Tethered 1,7‐Enynes Leading to Skeletally Diverse Polycyclic Chromen‐2‐ones

Jiang

Pan

et al. 2017

Chin. J. Chem.

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Catalytic bicyclization cascades of oxygen-tethered 1,7-enynes with simple cycloalkanes or aryl sulfonhydrazides have been established via subsequent multiple C-C bond-forming events from alkynyl/alkenyl functions, delivering a series of densely functionalized tetracyclic chromen-2-ones in a functional-group-compatible manner. In the former, Fe-catalyzed spiro-bicyclization involves radical addition, 6-exo-dig cyclization, H-abstraction and 5-endo-trig cyclization sequences under mild conditions, resulting in new spiro-fused cyclopenta[c]chromen-2-ones via dual α,α-C(sp 3 )-H abstractions. The latter enables in-situ sulfonylation and desulfonylation of oxygen-tethered 1,7-enynes to realize the construction of multiple C-C bonds, thereby leading to the formation of naphtho[2,3-c]chromen-6-ones.Example for the synthesis of 5a To a 10-mL Schlenk tube, 2-(phenylethynyl)phenyl methacrylate (1a, 0.20 mmol), tosylhydrazide (4a, 0.7 mmol), TBAI (0.02 mmol), and DCE (3.0 mL) as well as TBHP (5.5 mol/L in decane, 1.0 mmol) were successively added under argon conditions. The reaction system was then stirred at 80 ℃ for 24 h as monitored by TLC. After the completion of the reaction, the resulting mixture was concentrated under vacuum. Purification of the crude prod-Radical-Enabled Bicyclization Cascades of Oxygen-Tethered 1,7-Enynes Chin.

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Domino Hydroarylation–Cyclization Reaction: One‐Pot Synthesis of Indane‐Fused 3,4‐Dihydrocoumarins

Cited by 9 publications

References 65 publications

1,3-Dien-5-ynes: Versatile Building Blocks for the Synthesis of Carbo- and Heterocycles

1,3-Dien-5-ynes: Versatile Building Blocks for the Synthesis of Carbo- and Heterocycles

ChemInform Abstract: Domino Hydroarylation—Cyclization Reaction: One‐Pot Synthesis of Indane‐Fused 3,4‐Dihydrocoumarins.

Radical‐Enabled Bicyclization Cascades of Oxygen‐Tethered 1,7‐Enynes Leading to Skeletally Diverse Polycyclic Chromen‐2‐ones

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