Triflic acid promoted solvent free synthesis of densely functionalized furans

Vijayaprasad, Pulaganti; Venkanna, Avudoddi; Shanker, Medi; Kishan, Eslavath; Rao, P. Venkateswar

doi:10.1039/c7ra00489c

Cited by 5 publications

(1 citation statement)

References 49 publications

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“…With the support of previous reports ,, and the control experiments, a plausible reaction mechanism for the formation of indeno[2,1- c ]chromen-6(7 H )-ones 5 is depicted in Scheme . Initially, TfOH might activate the aldehyde group of substrate 3 and forms the indenol–ester intermediate B via cyclic carbocation A through the assistance of the double bond of acrylate.…”

Section: Resultsmentioning

confidence: 99%

Acid-Mediated Cascade Cyclization Pathway to Indeno[2,1-c]chromen-6(7H)-ones

Shekhar,

Satyanarayana

2023

J. Org. Chem.

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Developing mild and effective synthetic strategies for producing significant molecules starting from readily available starting materials is indispensable in organic synthesis. Herein, we present a triflic acid-driven dual cyclization pathway to produce functionalized indeno[2,1-c]chromen-6(7H)-ones from simple 2-formyl (or 2-acyl) cinnamate esters and phenols. Notably, this protocol enabled the construction of two C–C bonds and one C–O bond under metal-free reaction conditions via the activation of the unreactive ester moiety in a single pot. The isolation of intermediate indenol-ester might suggest self-intramolecular cycloaddition by the proximate double bond of the enoate ester with the o-carbonyl moiety, followed by an electrophilic attack with phenol and a subsequent cyclocondensation pathway. In addition, the photophysical properties have also been examined.

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Section: Resultsmentioning

confidence: 99%

Acid-Mediated Cascade Cyclization Pathway to Indeno[2,1-c]chromen-6(7H)-ones

Shekhar,

Satyanarayana

2023

J. Org. Chem.

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Synthesis of biologically relevant heterocyclic skeletons under solvent-free condition

Tripathi

Kumar

Rajkhowa

et al. 2021

Green Synthetic Approaches for Biologically Relevant Heterocycles

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9.9.6 Furans (Update 2024)

Kwiecień

2024

Knowledge Updates 2024/3

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This review is an update to the earlier Science of Synthesis contributions presenting methods for the synthesis of furans. It focuses on the literature published between 2011 and 2022. In the last decade, a number of new methods for the synthesis of furans from acyclic functionalized molecules have been developed. Many of the methods are based on (mixed) transition-metal catalysis, which induces several combinations of isomerizations, rearrangements, and cyclizations, leading to reactions that are termed cycloisomerizations. Multicomponent reactions for the synthesis of furans are also included.

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Triflic acid promoted solvent free synthesis of densely functionalized furans

Abstract: A simple, efficient and novel methodology has been developed for the synthesis of substituted furans mediated by triflic acid. In the reaction initial step involves the Friedel–Crafts arylation, followed by the dehydrative cyclization.

Cited by 5 publications

References 49 publications

Acid-Mediated Cascade Cyclization Pathway to Indeno[2,1-c]chromen-6(7H)-ones

Acid-Mediated Cascade Cyclization Pathway to Indeno[2,1-c]chromen-6(7H)-ones

Synthesis of biologically relevant heterocyclic skeletons under solvent-free condition

9.9.6 Furans (Update 2024)

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