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Metal-free ring expansion of indoles with nitroalkenes: A simple, modular approach to 3-substituted 2-quinolones

3-Substituted 2-quinolones are obtained via a novel metal-free transannulation reaction of 2-nitroolefins with 2-substituted indoles in polyphosphoric acid. This acid-mediated cascade transformation operates via the ANRORC (Addition of Nucleophile, Ring Opening, and Ring Closure) mechanism and can be used in combination with the Fisher indole synthesis to offer a practical three-component hetero-annulation approach to 2-quinolones from arylhydrazines, 2-nitroalkenes, and acetophenone. An alternative entry to this chemistry employing the alkylation of electron-rich arenes and hetarenes with 1-(2-indolyl)-2-nitroalkene has also been demonstrated.

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Quinoxaline | C8H6N828 | ChemSpider

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N,N-Dialkyl-2-phenylindol-3-ylglyoxylamides. A New Class of Potent and Selective Ligands at the Peripheral Renzodiazepine Receptor

We report the synthesis and the affinity data at both the peripheral (PBR) and the central benzodiazepine receptors of a series of N,N-dialkyl-2-phenylindol-3-ylglyoxylamide derivatives III, designed as conformationally constrained analogues of 2-phenylindole-3-acetamides II such as FGIN-1-27. Most of the new compounds showed a high specificity and affinity for PBR, with Ki in the nanomolar to subnanomolar range. The most potent ligands (4-7, 9, 13-27) stimulated steroid biosynthesis in rat C6 glioma cells with a potency similar to or higher than that of classical ligands. The SARs of this new class of compounds are discussed.

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ATP-citrate lyase as a target for hypolipidemic intervention. 2. Synthesis and evaluation of (3R*,5S*)-omega-substituted-3-carboxy-3,5- dihydroxyalkanoic acids and their gamma-lactone prodrugs as inhibitors of the enzyme in vitro and in vivo

A series of (3R*,5S*)-omega-substituted-3-carboxy-3,5-dihydroxyalkanoic acids have been synthesized and evaluated as inhibitors of the recombinant human form of ATP-citrate lyase. The best of these have K(i)’s in the 200- 1000 nM range. As the corresponding thermodynamically favored gamma-lactone prodrugs, a number of compounds are able to inhibit cholesterol and fatty acid synthesis in HepG2 cells and reduce plasma triglyceride levels in vivo. The best of these, compound 77, is able to induce clear hypocholesterolemic and hypotriglyceridaemic responses when administered orally to rat and dog. These results provide evidence to support the hypothesis that compounds which inhibit ATP-citrate lyase have the potential to be a novel class of hypolipidemic agent, which possess combined hypocholesterolemic and hypotriglyceridemic activities.

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Quinoxaline | C8H6N852 | ChemSpider

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Copper-catalyzed activation of dioxygen: Oxidative cyclization of 2-arylindoles

A series of unusual six-ring-fused heterocycles containing indole and quinoline skeletons was successfully synthesized by a copper-catalyzed reaction from 2-arylated indoles. Two new bonds were regioselectively formed from C-H and C-H coupling. 18O-Labelled experiments revealed that the dioxygen is not only the oxidant but also the reactant. Copyright

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Quinoxaline | C8H6N904 | ChemSpider

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Zn(OTf)2-catalysed indolylation and pyrrolylation of isatins: Efficient synthesis and biochemical assay of 3,3-di(heteroaryl)oxindoles

An efficient and cheap synthetic approach to 3,3-di(indolyl)oxindoles and 3,3-di(pyrrolyl) oxindoles has been developed via Zn(OTf)2 catalysed indolylation and pyrrolylation of isatins. A preliminary biochemical assay of the synthesized molecules in rodent models were performed to estimate the serum glutamate oxaloacetate transaminase and malondialdehyde levels. Indian Academy of Sciences.

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Quinoxaline – Wikipedia,
Quinoxaline | C8H6N893 | ChemSpider

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Organocatalytic Asymmetric Dearomative Oxyalkylation of Indoles Enables Access to C2-Quaternary Indolin-3-ones

A facile and efficient asymmetric dearomative oxyalkylation of indoles with TEMPO oxoammonium salt and a variety of aldehydes and ketones has been described. This metal-free approach provides a straightforward access to C2 quaternary oxindoles in high yields with excellent diastereo- and enantioselectivities under very mild conditions. The reaction goes smoothly even with only 0.1% equivalent catalyst. Moreover, 2-alkylindoles have proven to be suitable substrates for the first time.

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Rhodium-Catalyzed Regioselective Ortho C?H Olefination of 2-Arylindoles via NH-Indole-Directed C?H Bond Cleavage

In the past decades, C?H oxidative olefination of indole at C-2, C-3, C-4 and C-7 positions was well addressed. We report here a rhodium-catalyzed NH-indole-directed ortho C?H bond olefination of 2-arylindoles. This cross-dehydrogenative-coupling proved to be broad in substrate scope, tolerating a variety of functional groups. The synthesis of 6H-isoindolo[2,1-alpha]indoles via rhodium-catalyzed ortho C?H olefination and subsequent intramolecular aza-Michael reaction of 2-arylindoles was also demonstrated. (Figure presented.).

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Indole Derivatives as Potent Inhibitors of Larval Settlement by the Barnacle, Balanus amphitrite

A potent inhibitor of larval settlement by the barnacle, Balanus amphitrile, was isolated as 2,5,6-tribromo-1-methylgramine from a marine invertebrate.In comparative tests on the activity of related compounds, such compounds as 2-methylgramine and 2-methyl-3-(morpholinomethyl)-indole iyhibited potent inhibitory activity.The inhibitory activity toward larval settlement was found not to be due to toxicity but to a repellent effect.

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Access to Quaternary Stereogenic Centers via Rhodium(III)-Catalyzed Annulations between 2-Phenylindoles and Ketenes

Rh(III)-catalyzed C-H activation of arenes and mild oxidative [4 + 2] annulative coupling with ketenes have been realized. The uniquely high reactivity of the C(3) of 2-phenylindoles was successfully utilized to facilitate the reductive elimination process, leading to efficient synthesis of cyclic products with a quaternary carbon stereocenter.

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One-pot synthesis of polyhydropyrido[1,2-a]indoles and tetracyclic quinazolinones from 2-arylindoles using copper-mediated oxidative tandem reactions

We developed facile one-pot methods for the transformation of 2-arylindoles to polyhydropyrido[1,2-a]indoles and tetracyclic quinazolinones. The copper-catalyzed oxidation of 2-arylindoles to C-acylimines followed by aza-Diels?Alder reactions or oxidative ring-expansion reactions afforded significant polycyclic heterocycles.

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