Expedient, one-pot preparation of fused indoles via CAN-catalyzed three-component domino sequences and their transformation into polyheterocyclic compounds containing pyrrolo[1,2-a]azepine fragments

Suryavanshi, Padmakar A.; Sridharan, Vellaisamy; Menéndez, J. Carlos

doi:10.1039/c004703a

Cited by 52 publications

(28 citation statements)

References 53 publications

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“…and its derivatives display a broad variety of powerful and therapeutically fascinating biological activities [86]. For example, serotonin alkaloid is a bioactive alkaloid known as a neurotransmitter in the cardiovascular system, blood cells and the peripheral, and central nervous system.…”

Section: Indole Indole Ring System Is a Prevalent Structural Motif Ementioning

confidence: 99%

Bioactive Phytochemicals: Bioactivity, Sources, Preparations, and/or ModificationsviaSilver Tetrafluoroborate Mediation

Achilonu

Umesiobi

2015

Journal of Chemistry

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This review provides an overview of the biological activities, natural occurrences, and the silver tetrafluoroborate- (AgBF4-) mediated synthesis of proanthocyanidins, glycosides, N-heterocyclic alkaloid analogues (of pyrrole, morphine, quinoline, isoquinoline, and indole), furan analogues, and halocompounds. AgBF4has been reviewed as an effective reaction promoter, used extensively in the synthesis of relevant biologically active compoundsviacarbon-carbon and carbon-heteroatom bonds formation. The literatures from 1979 to April 2014 were reviewed.

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Section: Indole Indole Ring System Is a Prevalent Structural Motif Ementioning

confidence: 99%

Bioactive Phytochemicals: Bioactivity, Sources, Preparations, and/or ModificationsviaSilver Tetrafluoroborate Mediation

Achilonu

Umesiobi

2015

Journal of Chemistry

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“…Kuckländer Applications of the Nenitzescu Indole SynthesisMenéndez and colleagues used a three-component cerium(IV) ammonium nitrate (CAN) domino reaction to effect the synthesis of 5-hydroxybenzo[g]indoles and 5hydroxyindoles in yields up to 96% (equations 2, 3)[50]. The reaction presumably proceeds via enaminone 54 and activation of the quinone by CAN.…”

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confidence: 99%

Nenitzescu 5‐Hydroxyindole Synthesis

Gribble

2016

Indole Ring Synthesis

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“…During the course of our research in this area, an unexpected product, diethyl 9,10-anthraquinone-1,3dicarboxylate (3a), was discovered involving the reac- (1)], [22] however, where the Nenitzescu reaction was used to obtain fused indoles, our own work led to the formation of a different product 3a, with the difference in the products being attributed to the presence of an H atom instead of a methyl group at the R 2 position of the b-enamino esters under the same conditions as reported by MenØndez (Table 1, entry 1).…”

mentioning

confidence: 99%

“…[33] Then we proposed a tentative mechanism for this oxidative aromatization process (Scheme 1). [22] In conclusion, we have developed an exciting new strategy for the construction of polysubstituted aromatic core derivatives from the oxidative aromatization reaction of quinones or N-substituted maleimides with b-enamino esters under an oxygen atmosphere. Scope of the current reaction for the formation of 3. pling reaction between A and 2a giving rise to intermediate B.…”

mentioning

confidence: 99%

The Construction of Polysubstituted Aromatic Core Derivatives via a Cycloaddition/Oxidative Aromatization Sequence from Quinone and β‐Enamino Esters

Huang

et al. 2014

Adv Synth Catal

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An unexpected strategy has been discovered for the construction of polysubstituted aromatic core derivatives from the reaction of quinones or N-substituted maleimides with b-enamino esters by a cycloaddition/oxidative aromatization sequence that provides products contrary to those delivered by the Nenitzescu reaction. The current method provides a highly favorable synthetic strategy for the efficient construction of important therapeutic agents containing polysubstituted aromatic core structures.b-Enamino esters are versatile intermediates, which are often used for the synthesis of heterocycles, and compounds of this class are also common pharmacophores in a number of important medicinal agents. [1] Furthermore, b-enamino esters are employed as key starting reagents for the synthesis of substituted pyra-Quinones represent one of the most widely distributed structural classes in nature, [17] and compounds belonging to this class can be found in a large number of important pharmacophores [18] associated with anti-cancer, antibacterial, antimalarial, fungicidal, and antiparasitic agents. [19] Based on the recent resurgence of interest in the functionalization of quinone structures [20] and the application of b-enamino esters in organic synthesis, [21] we became interested in further exploring the reactions of b-enamino esters with quinones.During the course of our research in this area, an unexpected product, diethyl 9,10-anthraquinone-1,3dicarboxylate (3a), was discovered involving the reaction of 1,4-naphthoquinone (1a) with ethyl-3-(methylamino)acrylate (2a) [Eq. (2)]. Contrary to similar work reported by MenØndez et al. [Eq.(1)], [22] however, where the Nenitzescu reaction was used to obtain fused indoles, our own work led to the formation of a different product 3a, with the difference in the products being attributed to the presence of an H atom instead of a methyl group at the R 2 position of the b-enamino esters under the same conditions as reported by MenØndez (Table 1, entry 1).Furthermore, among various kinds of naturally occurring substances, quinone derivatives are common and very important. [23] For example, rhein, [24] physcion, [23d,25] aloe-emodin; [26] emodin [27] and chrysophanol [28] exhibit antifungal activity. [23d,29] Especially emodin, which is purified from the Chinese medicinal herb rhubarb, has inhibitory activity against ERK phosphorylation in PC3 cells induced by EGF. [30] Moreover, aloe-emodin might represent a conceptually new lead antitumor drug taking into account its unique cytotoxicity profile and mode of action. [26a] Besides, DMAC, aloesaponarin I and aloesaponarin II also show good antibacterial activity (Figure 1). [31] Based on this initial result and the significance of these unexpected polysubstituted aromatic cores in related drugs, we became interested in developing a greater understanding of this reaction between 1,4-

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Expedient, one-pot preparation of fused indoles via CAN-catalyzed three-component domino sequences and their transformation into polyheterocyclic compounds containing pyrrolo[1,2-a]azepine fragments

Cited by 52 publications

References 53 publications

Bioactive Phytochemicals: Bioactivity, Sources, Preparations, and/or ModificationsviaSilver Tetrafluoroborate Mediation

Bioactive Phytochemicals: Bioactivity, Sources, Preparations, and/or ModificationsviaSilver Tetrafluoroborate Mediation

Nenitzescu 5‐Hydroxyindole Synthesis

The Construction of Polysubstituted Aromatic Core Derivatives via a Cycloaddition/Oxidative Aromatization Sequence from Quinone and β‐Enamino Esters

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