CuI-Catalyzed Coupling of <i>gem</i>-Dibromovinylanilides and Sulfonamides: An Efficient Method for the Synthesis of 2-Amidoindoles and Indolo[1,2-<i>a</i>]quinazolines

Kiruthika, Selvarangam E.; Perumal, Paramasivan T.

doi:10.1021/ol403365t

Cited by 65 publications

(18 citation statements)

References 56 publications

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“…The unique process can offer useful and diverse N-fused heterocycles for medicinal chemistry and combinatorial chemistry (Yang et al, 2012). In an interesting study, Kiruthika and Perumal disclosed a copper-catalyzed one-pot, intermolecular procedure for the rapid construction of indolo[1,2-a]quinazoline derivatives 93 from the commercially available gem-dibromovinylanilide derivatives 91 and N-tosyl-o-bromobenzamide derivatives 92 by employing Cs 2 CO 3 and 1,10-phen in refluxing THF, followed by refluxing under basic conditions (Kiruthika and Perumal, 2014). The protocol operated well with a diverse range of N-tosyl-obromobenzamide derivatives 92 and converted into respective quinazolines with good isolated yields (70-81%) (Scheme 24C).…”

Section: Copper-mediated Catalytic Systemsmentioning

confidence: 99%

Chemical Insights Into the Synthetic Chemistry of Quinazolines: Recent Advances

Faisal

Saeed

2021

Front. Chem.

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In medicinal chemistry, one of the most significant heterocyclic compounds are quinazolines, possessing broad range of biological properties such as anti-bacterial, anti-fungal, anti-HIV, anti-cancer, anti-inflammatory, and analgesic potencies. Owing to its numerous potential applications, in the past two decades, there is an increase in the importance of designing novel quinazolines, exploring promising routes to synthesize quinazolines, investigating different properties of quinazolines, and seeking for potential applications of quinazolines. The present review article describes synthesis of quinazolines via eco-friendly, mild, atom-efficient, multi-component synthetic strategies reported in the literature. The discussion is divided into different parts as per the key methods involved in the formation of quinazoline skeletons, aiming to provide readers an effective methodology to a better understanding. Consideration has been taken to cover the most recent references. Expectedly, the review will be advantageous in future research for synthesizing quinazolines and developing more promising synthetic approaches.

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Section: Copper-mediated Catalytic Systemsmentioning

confidence: 99%

Chemical Insights Into the Synthetic Chemistry of Quinazolines: Recent Advances

Faisal

Saeed

2021

Front. Chem.

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“…Different reagents were tested for the bromination of 15, i.e. CBr 4 , HBr and NBS, [9,10,20,21] with yields of 31%, 60% and 86% respectively, but NBS turned out to be the most efficient reagent.…”

Section: Model Compound 5 and Non-conjugated Dendron Precursormentioning

confidence: 99%

New porphyrin dendrimers with fluorenyl-based connectors: a simple way to improving the optical properties over dendrimers featuring 1,3,5-phenylene connectors

et al. 2020

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“…(Scheme 11). 10 The method involves the intermolecular coupling of gem-dibromovinylanilide 21 and sulfonamides 22 using Cu(I) iodide as the catalyst.…”

Section: Review Syn Thesismentioning

confidence: 99%

Recent Advances in the Regioselective Synthesis of Indoles via C–H Activation/Functionalization

Kumar

Sharma

2018

Synthesis

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Indole is an important heterocyclic motif that occurs ubiquitously in bioactive natural products and pharmaceuticals. Immense efforts have been devoted to the synthesis of indoles starting from the Fisher indole synthesis to the recently developed C–H activation/functionalization-based methods. Herein, we have reviewed the progress made on the regioselective synthesis of functionalized indoles, including 2-substituted, 3-substituted and 2,3-disusbstituted indoles, since the year 2010.1 Introduction2 Metal-Catalyzed Synthesis of 2-Substituted Indoles3 Metal-Catalyzed Synthesis of 3-Substituted Indoles4 Metal-Free Synthesis of 3-Substituted Indoles5 Metal-Catalyzed 2,3-Disubstituted Indole Synthesis5.1 Metal-Catalyzed Intramolecular 2,3-Disubstituted Indole Synthesis5.2 Metal-Catalyzed Intermolecular 2,3-Disubstituted Indole Synthesis6 Metal-Free 2,3-Disubstituted Indole Synthesis6.1 N-Protected 2,3-Disubstituted Indole Synthesis6.2 N-Unprotected 2,3-Disubstituted Indole Synthesis7 Applications8 Summary and Outlook

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CuI-Catalyzed Coupling of gem-Dibromovinylanilides and Sulfonamides: An Efficient Method for the Synthesis of 2-Amidoindoles and Indolo[1,2-a]quinazolines

Cited by 65 publications

References 56 publications

Chemical Insights Into the Synthetic Chemistry of Quinazolines: Recent Advances

Chemical Insights Into the Synthetic Chemistry of Quinazolines: Recent Advances

New porphyrin dendrimers with fluorenyl-based connectors: a simple way to improving the optical properties over dendrimers featuring 1,3,5-phenylene connectors

Recent Advances in the Regioselective Synthesis of Indoles via C–H Activation/Functionalization

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