Quinoneimines in the Nenitzescu reaction

Lyubchanskaya, V. M.; Panisheva, E. K.; Savina, S. A.; Алексеева, Л. М.; Шашков, А. С.; Граник, В. Г.

doi:10.1007/s11172-006-0024-6

Cited by 8 publications

(2 citation statements)

References 7 publications

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“…The synthesis of the benzofuran derivatives is outlined in Scheme S1 (ESI †) and follows a published route to obtain amino-substituted benzofuran 1. 37,38 The route to access the benzofuran derivatives begins with a nucleophilic substitution reaction with commercially available sulfonyl chlorides and compound 1 to give substituted benzofurans B1-B7 (Scheme S1, ESI †).…”

Section: High-throughput Screening and Validation Of Hitsmentioning

confidence: 99%

Identifying ligands for the PHD1 finger of KDM5A through high-throughput screening

Ortiz,

Longbotham,

Qin

et al. 2024

RSC Chem. Biol.

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Section: High-throughput Screening and Validation Of Hitsmentioning

confidence: 99%

Identifying ligands for the PHD1 finger of KDM5A through high-throughput screening

Ortiz,

Longbotham,

Qin

et al. 2024

RSC Chem. Biol.

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“…Especially, reactions of N-aryl-substituted enaminoesters at low temperatures are known to generate 6-hydroxyindoles [41]. O-acylated 4,5-dihydroxyindoles are Besides 5-hydroxyindoles and benzofurans, a diverse range of alternative reaction products, including 6-hydroxyindoles [32][33][34], O-acylated 4,5-dihydroxyindoles [33,[35][36][37][38], pyrroloindoles [39], furo [2,3-f ]benzofurans [40], and dimeric indoles [35], have been isolated (Scheme 2). Moreover, 6-hydroxyindoles are formed in the so-called 'anti-Nenitzescu reaction' which occurs via a 1,2-addition followed by an intramolecular Michael addition [15,23].…”

Section: Introductionmentioning

confidence: 99%

Exploration of the Divergent Outcomes for the Nenitzescu Reaction of Piperazinone Enaminoesters

et al. 2023

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The Nenitzescu reaction is a condensation reaction between an enamine and a quinone, which can give rise to a wide variety of reaction products depending on the nature of the starting material and the reaction conditions. The most commonly observed products are 5-hydroxyindoles and 5-hydroxybenzofurans. Both classes are of interest since they are known to possess a variety of promising bioactivities. Despite the high chemodivergency for this reaction, it remains an interesting synthetic strategy thanks to the mild reaction conditions, easily accessible starting materials and simple reaction procedures. For these reasons, our research group investigated the Nenitzescu reaction of piperazinone enaminoesters, resulting in the unexpected formation of rearranged 2-imidazolidinone benzofurans. In this work, we aimed to develop reaction conditions that favor the formation of 5-hydroxyindoles via an extensive, multivariate optimization study. This led to valuable insights into the parameters that influence regio- and chemoselectivity. Furthermore, two novel products were obtained, a pyrrolo[2,3-f]indole and a benzofuranone, both of which are rarely reported in the literature.

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Nenitzescu Indole Synthesis

2010

Comprehensive Organic Name Reactions and Reagents

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The synthesis of a 5‐hydroxyindole derivative involving the condensation between a 1,4‐benzoquinone and a β‐amino‐α,β‐unsaturated compound and subsequent cyclization is generally known as the Nenitzescu indole synthesis. It has been observed that the synthesized indole derivatives by this reaction are restricted to those with an electron withdrawing group at position 3. In addition, the completion of this reaction requires an appropriate oxidizing agent to convert the initial adduct into the indole derivative. From monosubstituted quinone, 4‐, 6‐ and 7‐substituted 5‐hydroxyindole derivatives all are possible products, but 6‐substituted isomer is the one normally obtained. This reaction has been modified by using quinone mono‐ketals to control the regioselectivity. This reaction is particularly useful for the preparation of 5‐hydroxyindole derivatives.

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Quinoneimines in the Nenitzescu reaction

Abstract: The Nenitzescu reaction involving quinoneimines was studied; new 5 aminoindole, 5 aminobenzofuran, and 9 aminochromenopyridine derivatives were synthesized.

Cited by 8 publications

References 7 publications

Identifying ligands for the PHD1 finger of KDM5A through high-throughput screening

Identifying ligands for the PHD1 finger of KDM5A through high-throughput screening

Exploration of the Divergent Outcomes for the Nenitzescu Reaction of Piperazinone Enaminoesters

Nenitzescu Indole Synthesis

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