Regioselectivity of Friedländer Quinoline Syntheses

Diedrich, Claas Lüder; Haase, Detlev; Saak, Wolfgang; Christoffers, Jens

doi:10.1002/ejoc.200701179

Cited by 29 publications

(28 citation statements)

References 40 publications

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“…The reaction was then performed employing other 2‐aminobenzaldehydes, using catalyst bcmim‐Ca1 under the best reaction conditions; namely, microwave heating at 80 °C for 90 min in the presence of 10 equiv. pentane‐2,4‐dione (Scheme ).…”

Section: Resultsmentioning

confidence: 99%

Versatile Barium and Calcium Imidazolium‐Dicarboxylate Heterogeneous Catalysts in Quinoline Synthesis

et al. 2017

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This article details the development of heterogeneous catalysts based on calcium and barium in combination with the organic linker 1,3‐bis(carboxymethyl)imidazolium (bcmim). The linker and the materials from alkaline earth metals are easily prepared under very smooth conditions. The use of linkers with different counterions (Cl or Br) provided different materials. Calcium‐ and barium‐based catalysts were successfully employed in the preparation of quinoline derivatives from ketones and 2‐aminoarylaldehydes or 2‐aminoarylketones. In general, barium‐based catalysts provided better results than calcium, although the latter are an excellent complement for certain substrates. Thus, a notable feature of such catalysts is the possibility of accessing a variety of complementary heterogeneous catalytic systems, rendering the catalysis adaptive to the reactant.||||||

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Section: Resultsmentioning

confidence: 99%

Versatile Barium and Calcium Imidazolium‐Dicarboxylate Heterogeneous Catalysts in Quinoline Synthesis

et al. 2017

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“…The other diastereoisomer 21 of the scaffold was submitted to Friedländer quinoline synthesis with 2‐aminobenzaldehyde; the latter was obtained by reduction of 2‐nitrobenzaldehyde with iron powder/hydrochloric acid directly before the quinoline synthesis . The tetracyclic product 24 was obtained in 75 % yield as a single regioisomer (Scheme ).…”

Section: Resultsmentioning

confidence: 99%

“…Intermediate compound 6 shall actually, after hydrogenation, be submitted to indole (product 7 ) and quinoline (product 8 ) annulation. Although two regioisomers of such annulation reactions could be formed (linear vs. angular), preceding investigations on the decalone scaffold revealed, that the cis ‐diastereoisomer resulted in angular annulation, whereas the trans ‐annulated motif furnished linear indoles and quinolines (Scheme ) …”

Section: Introductionmentioning

confidence: 99%

Aminodecalone Scaffolds – Enantioselective Synthesis, Indole and Quinoline Annulation

2018

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Optically active benzo[b]carbazole and benzo[b]acridine derivatives were prepared by Fischer indole or Friedländer quinoline annulation from 2‐oxodecalone‐4a‐carboxylates with a quaternary stereocenter. As an additional point for diversification, the target compounds carry a nitro function, which was transformed to an amide or lactam after reduction. The scaffold itself was accessed by asymmetric, copper catalyzed Michael reaction of a β‐oxoester with methyl vinyl ketone utilizing l‐valine diethyl amide as chiral auxiliary. Two enantiopure, epimeric compounds were obtained with 99 % ee and 92 % ee, which were separated and in parallel sequences submitted to intramolecular aldol reaction and catalytic hydrogenation furnishing the 2‐oxodecalone scaffolds. As a precursor for the primary amino group, the scaffolds contained a nitro function at their 6‐positions, which was reduced at the end of the synthetic sequence. The relative and absolute configurations of all three stereocenters were established by X‐ray crystallography.

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“…The residue was purified by column chromatography on silica gel (EtOAc/hexane, 20:80) to give 10 (1.05 g, 87%) as a pale yellow solid: mp 38−40°C (lit. 12 (12). Compound 11 (864 mg, 4.0 mmol) was added to 3 mL of 40% sulfuric acid at room temperature, and then 3 g of ice was added.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Synthesis and Antiproliferative Activity Evaluation of the Disulfide-Containing Cyclic Peptide Thiochondrilline C and Derivatives

Vippila

Cuny

2015

J. Nat. Prod.

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Thiochondrilline C (4) was previously isolated from Verrucisispora sp. and reported to have moderate cytotoxicity against human lung adenocarcinoma cells. Herein, we report the synthesis of thiochondrilline C by N-terminal peptide extension, oxidative disulfide bond formation, and heterocycle installation as key steps. Antiproliferative activities for the prepared natural product and several derivatives against the NCI 60 cancer cell line panel are also described. Derivative 22 was identified as a moderately potent antiproliferative agent (50% growth inhibition (GI50) = 0.2-12.2 μM) with leukemia (average GI50 = 1.8 ± 0.1 μM) and colon (average GI50 = 2.4 ± 0.3 μM) cells being most sensitive.

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Regioselectivity of Friedländer Quinoline Syntheses

Cited by 29 publications

References 40 publications

Versatile Barium and Calcium Imidazolium‐Dicarboxylate Heterogeneous Catalysts in Quinoline Synthesis

Versatile Barium and Calcium Imidazolium‐Dicarboxylate Heterogeneous Catalysts in Quinoline Synthesis

Aminodecalone Scaffolds – Enantioselective Synthesis, Indole and Quinoline Annulation

Synthesis and Antiproliferative Activity Evaluation of the Disulfide-Containing Cyclic Peptide Thiochondrilline C and Derivatives

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