Efficient synthesis of 3-substituted indoles through a domino gold(I) chloride catalyzed cycloisomerization/C3-functionalization of 2-(alkynyl)anilines

Praveen, Chandrasekar; Karthikeyan, K.; Perumal, Paramasivan T.

doi:10.1016/j.tet.2009.09.019

Cited by 65 publications

(29 citation statements)

References 108 publications

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“…The scope of the methodology was extended by the use of sugar‐derived chiral Michael acceptors. In all cases examined, the D‐gluco isomer was formed as the major isomer and the L‐ido as the minor product (Scheme ) 59…”

Section: Gold‐catalyzed Sequential Reactions Of 2‐alkynylanilinesmentioning

confidence: 97%

Synthesis of Indole Derivatives from 2‐Alkynylanilines by Means of Gold Catalysis

Abbiati¹,

Marinelli

Rossi³

et al. 2013

Israel Journal of Chemistry

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The peculiar features of gold(III) and gold(I) species include exceptional carbophilicity and, at the same time, lone pair affinity. Such a combination offers many advantages for the development of more sustainable approaches to the synthesis of indole derivatives from readily available 2‐alkynylanilines. This mini‐review critically summarizes the literature reports in this field, with the aim to encourage further research activities in this promising area.

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Section: Gold‐catalyzed Sequential Reactions Of 2‐alkynylanilinesmentioning

confidence: 97%

Synthesis of Indole Derivatives from 2‐Alkynylanilines by Means of Gold Catalysis

Abbiati¹,

Marinelli

Rossi³

et al. 2013

Israel Journal of Chemistry

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“…Most approaches for the synthesis of indole and benzofuran derivatives require an ortho ‐disubstituted arene group, which upon cyclization affords the desired compound . Usually, these synthetic methodologies involve the use of transition metal complexes, such as cobalt, copper,, gold, palladium, ruthenium, platinum or indium as catalysts for the synthesis of these moieties. For example, a common approach constitutes the metal‐catalysed cyclization of ortho ‐substituted anilines with alkynes (Scheme , A ).…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Benzofuran and Indole Derivatives Catalyzed by Palladium on Carbon

et al. 2019

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Benzofurans and indoles are key moieties in many natural products and pharmaceuticals. Herein, we describe a cheap and easy‐to‐execute strategy for the synthesis of benzofurans and indoles, employing Pd/C as the promoter. A variety of substituted allyl‐anilines and allyl‐phenols were converted into the desired products in good to excellent yields. Recycling of Pd/C was possible up to five cycles, keeping similar levels of reactivity.

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“…As part of our research interests on new synthetic methodologies for pharmacologically important molecules, [17][18][19][20][21][22][23][24][25][26][27][28][29][30][31][32] we have demonstrated the catalytic application of gold for the construction of various structurally challenging carboand heterocycles. [33][34][35][36][37][38][39][40][41][42][43][44][45][46][47][48] In order to circumvent the aforementioned limitations linked with the synthesis of dihydropyrimidines, coupled with our research interests in gold catalysis, we have now investigated the synthesis of both tetrahydropyrimidines and octahydroquinazolines under the catalytic influence of gold. Towards this end, we herein report an improved methodology for the solvent-free synthesis of tetrahydrohydropyrimidine / octahydroquinazoline derivatives under mechanochemical conditions in presence of Au(III) as catalyst.…”

Section: Introductionmentioning

confidence: 99%

Gold catalyzed synthesis of tetrahydropyrimidines and octahydroquinazolines under ball milling conditions and evaluation of anticonvulsant potency

Vadivelu¹,

Raheem²,

Sugirdha³

et al. 2017

Arkivoc

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A fast, mechanochemical and solvent-free synthesis of substituted tetrahydropyrimidines and octahydroquinazolines under Au(III)-catalysis has been developed. The practical feasibility, eco-friendliness and operational simplicity of this chemistry is exemplified by ball milling three components such as formaldehyde, amines and 2-butynedioates/dimedone in a shaker mill for as little as five minutes, thus avoiding the requirement of undesirable solvents and long reaction times. Moreover, this protocol furnishes the target compounds in high yields without any side products and in some cases offers products with excellent regioselectivity. Out of the 26 compounds screened for anticonvulsant potency, 11 compounds exhibited comparable activity against a standard drug.

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Efficient synthesis of 3-substituted indoles through a domino gold(I) chloride catalyzed cycloisomerization/C3-functionalization of 2-(alkynyl)anilines

Cited by 65 publications

References 108 publications

Synthesis of Indole Derivatives from 2‐Alkynylanilines by Means of Gold Catalysis

Synthesis of Indole Derivatives from 2‐Alkynylanilines by Means of Gold Catalysis

Synthesis of Benzofuran and Indole Derivatives Catalyzed by Palladium on Carbon

Gold catalyzed synthesis of tetrahydropyrimidines and octahydroquinazolines under ball milling conditions and evaluation of anticonvulsant potency

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