New reactions of 2-substituted indoles

Dave, Vinod; Warnhoff, E. W.

doi:10.1139/v76-147

Cited by 11 publications

(7 citation statements)

References 8 publications

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“…402 Bergman found that 2-ethylindole reacts with N,N-dimethylacetamide dimethylacetal 179 to yield BIM 180 in the absence of a catalyst (Scheme 64). 355 Also 2-methylindole with ethyl acetate and sodium ethoxide, 403 when refluxed in acetyl chloride 404,405 or in acetyl cyanide and ethanolic potassium hydroxide 406,407 gives the BIM 181 (eq 1). The same structure was also reported from the reaction of indole and acetic anhydride in acetic acid.…”

Section: 3′-bims From Indoles Reacting With Other Functional Groupsmentioning

confidence: 99%

Bis- and Trisindolylmethanes (BIMs and TIMs)

et al. 2009

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Section: 3′-bims From Indoles Reacting With Other Functional Groupsmentioning

confidence: 99%

Bis- and Trisindolylmethanes (BIMs and TIMs)

et al. 2009

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“…The background reactions were further reduced by changingt he reductant to manganese powder (41 %y ield, entry 3). We also briefly investigated other catalyst precursors, all of whichg ave inferiorr e-sults (entries [4][5][6][7][8][9]. Again, no product was observed in the absence of the catalyst (entry 10).…”

Section: -Iminoindolinesmentioning

confidence: 99%

“…These compounds tend to undergo oxidatived imerization or similard ecompositionr eactions, are sensitive to light and air,a nd cannotb ep urified by chromatography. [3,4] As aconsequence, the major approaches have remained the tradi-tional indole nitration and azidation reactions followed by reductiont ot he free amine [3] and ionic cyclization reactions. [1,2,5] Modern catalytic methods, on the other hand, give rise to electron-poora nd/or protected derivatives that require deprotection or subsequent functional group interconversion steps.…”

Section: Introductionmentioning

confidence: 99%

“…The main reason behind the synthetic challenge is the inherent instability of the unprotected, electron‐rich 3‐aminoindoles and ‐pyrroles, which would be ideal building blocks (Scheme a). These compounds tend to undergo oxidative dimerization or similar decomposition reactions, are sensitive to light and air, and cannot be purified by chromatography . As a consequence, the major approaches have remained the traditional indole nitration and azidation reactions followed by reduction to the free amine and ionic cyclization reactions .…”

Section: Introductionmentioning

confidence: 99%

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Development, Scope, and Applications of Titanium(III)‐Catalyzed Cyclizations to Aminated N‐Heterocycles

Leijendekker

Weweler

Leuther

et al. 2019

Chemistry A European J

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The exceptionally mild conditions of at itanium(III)-catalyzed cyclization reactionp aired with ac onvenient acid/base extraction have enabled the straightforward synthesis, isolation, and direct N-functionalization of amino heterocycles such as 3-aminoindoles and -pyrroles.T he unprotected heterocycles are ideal building blocks fort he installation of aminatedi ndoles and pyrroles into target molecules, but their sensitivity has previously impeded their synthesis by modernc atalytic methods. This full paper presents the development and extended scope of the new cyclization methodology.T he transformation of the products into fused bis-indoles is also demonstrated along with the discoveryo f an unusual palladium-catalyzed reductive biphenyl coupling reaction. The titanium(III)-catalyzed cyclization hasa lso been appliedt ot he synthesis of substituted 3-iminoindolines, which are of potential interestf or applicationsi nn atural product synthesis and exhibit tunable blue-to-green fluorescence properties.Supporting information and the ORCID identification number(s) for the author(s) of this articlecan be found under: https://doi.org/10.1002/chem.201805909.Scheme1.a) Usualand ideal scenarios for the catalytic synthesis of 3-aminoindole and -pyrrole building blocks. b) Envisionedtitanium(III)-catalyzed cyclization to furnish unprotected, electron-rich 3-aminoheterocycles.

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“…1,1‐Bis(2‐phenyl‐3‐indolyl)ethylene ( 4a ) was synthesized conventionally by refluxing 2‐phenylindoles and acetyl chloride (RANKEM, Gurugram, Haryana, India) in alcohol for 4–5 h . To explore the versatility of the procedure, we have reacted of various substituted‐2‐phenylindoles ( 1a–e ) with acetyl chloride in the presence of ZnO nanocatalyst via two approaches, that is, classical and green grindstone mechanochemical route.…”

Section: Introductionmentioning

confidence: 99%

An Efficient Approach for the Synthesis of 1,1‐bis(2‐phenyl‐3‐indolyl)ethylene Using ZnO Nanocatalyst

Madan

2017

Journal of Heterocyclic Chem

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A combination of nanocatalyst and green chemical route (mechanochemistry) was used to generate a series of substituted 1,1‐bis(2‐phenyl‐3‐indolyl)ethylene derivatives (4a–e) that were synthesized by reacting various 2‐arylindoles (1a–e) and acetyl chloride in absolute alcohol with or without ZnO nano as catalyst via two approaches, that is, classical and green solvent‐free route. The use of ZnO nano particles is preferred to absence of catalyst in terms of short reaction time and mild reaction conditions with reusability of the catalyst. All the synthesized compounds were characterized on the basis of their elemental and spectral data (IR, proton magnetic resonance, 13C NMR, and Mass).

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New reactions of 2-substituted indoles

Cited by 11 publications

References 8 publications

Bis- and Trisindolylmethanes (BIMs and TIMs)

Bis- and Trisindolylmethanes (BIMs and TIMs)

Development, Scope, and Applications of Titanium(III)‐Catalyzed Cyclizations to Aminated N‐Heterocycles

An Efficient Approach for the Synthesis of 1,1‐bis(2‐phenyl‐3‐indolyl)ethylene Using ZnO Nanocatalyst

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