Tandem Wittig – Reductive annulation decarboxylation approach for the synthesis of indole and 2-substituted indoles

Volvoikar, Prajesh S.; Tilve, Santosh G.

doi:10.1016/j.tetlet.2018.04.001

Cited by 8 publications

(5 citation statements)

References 47 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Compound 5 was saponified with NaOH to give compound 8 in quantitative yield. The decarboxylation was carried out in diphenyl ether at 260 °C to afford intermediate 9 in 87% yield . Compound 9 was then methylated using dimethyl sulfate to afford compound 10a in 87% yield.…”

Section: Results and Discussionmentioning

confidence: 99%

“…The decarboxylation was carried out in diphenyl ether at 260 °C to afford intermediate 9 in 87% yield. 18 Compound 9 was then methylated using dimethyl sulfate to afford compound 10a in 87% yield. At last, the formation of the isatin derivative 11 was done using I 2 O 5 as the oxidative reagent to generate the target compound with a yield of 92%.…”

Section: ■ Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Biosourced Vanillin-Based Building Blocks for Organic Electronic Materials

et al. 2021

View full text Add to dashboard Cite

Forest biomass is viewed as a significant source of organic carbon and thus the ideal replacement of petroleum products. From the resources derived from biomass, lignocellulose is the most abundant biobased material on earth. One of the aromatic added value compounds obtained from the depolymerization of lignin is vanillin. Here, we report the preparation of new compounds having benzothiophene, indole, isatin, benzofuroxan, benzofurazan, benzothiadiazole, and phthalimide heteroaromatic ring structures. More precisely, our results show that vanillin can be used as a biosourced starting material for the preparation of a variety of aromatic dibrominated monomers. X-ray crystallography on single crystals was also performed to obtain meaningful information on their solid-state ordering. This work opens the way to new, sustainable, biosourced aromatic materials (small molecules or polymers) for organic electronics.

show abstract

Section: Results and Discussionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

Biosourced Vanillin-Based Building Blocks for Organic Electronic Materials

et al. 2021

View full text Add to dashboard Cite

show abstract

“…In this regard, there are many traditional methods for the preparation of indole derivatives including Fischer reaction, 18,19 Bischler reaction, 20 Reissert reaction, 21 Bartoli reaction, 22 and Leimgruber-Batcho reaction. 23 Recently, new strategies have been developed for the synthesis of indole derivatives; these include: various metal-catalyzed, [24][25][26][27][28][29] multi-component method, 30 cyclization reaction, 31 Wittig reactions, 32 and various other methods. [33][34][35][36] Most of these protocols appear to suffer from some drawbacks such as tedious experimental procedures, difficult reaction conditions, multiple synthetic steps, low yields, and usage of expensive catalysts and reagents.…”

Section: Figure 1 Selected Bioactive Molecules Indolesmentioning

confidence: 99%

One-pot, regioselective synthesis of functionalized indole derivatives: a three-component domino reaction of arylamine, arylglyoxal, and 4-hydroxycoumarin or 4-hydroxy-6-methyl-2-pyrone

Mehrabi¹,

Dastouri²,

Asadi³

et al. 2020

Arkivoc

View full text Add to dashboard Cite

A metal free, one-pot tandem synthetic routes for functionalized indole derivatives has been established. An efficient three-component reaction was designed with incorporation of Knoevenagel condensation followed by inter-, and intramolecular nucleophilic addition reaction in one-pot under mild condition. The structural diversities of the synthesized compounds have been confirmed spectroscopically, by IR, 1 H-and 13 C NMR, and elemental analyses which agree with the proposed structures.

show abstract

“…Nitroarenes, directly obtained from the nitration of the parent arenes, are highly versatile and common aromatic building blocks for access to the corresponding aryl amine, and indole involving the use of the nitro group as the nitrogen source via reduction. Nevertheless, given that the N atom in the nitro group has a high oxidation state, it is ideal to explore more redox-economic reactions for further functionalization.…”

mentioning

confidence: 99%