Synthesis of substituted 1,2-dihydroquinolines and quinolines using ene–ene metathesis and ene–enol ether metathesis

Arisawa, Mitsuhiro; Theeraladanon, Chumpol; Nishida, Atsushi; Nakagawa, Masako

doi:10.1016/s0040-4039(01)01714-2

Cited by 115 publications

(35 citation statements)

References 13 publications

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“…[65] N,N-Diallylaniline derivatives have also been shown to be substrates for the synthesis of various pyrroles using microwave or ultrasound activation. [64,66] Syntheses of dihydroquinolines 101 [68] and 103a [67] were described using RCM catalyzed by first-generation Grubbs catalyst 2 (Scheme 40). A better yield was observed for RCM of N-benzylamine 100 than for its N-Boc-protected analogue, probably because of the formation of chelated intermediates between ruthenium complexes and the Boc carbonyl oxygen.…”

Section: Ruthenium-catalyzed Metathesis Of Phenylamines and Analoguesmentioning

confidence: 99%

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Olefin Metathesis of Amine‐Containing Systems: Beyond the Current Consensus

Compain¹

2007

Adv Synth Catal

162

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Olefin metathesis is one of the most powerful synthetic tool to access amine-containing heterocycles and alkaloids. A major drawback associated with the use of amines concerns their ability to coordinate to metal-alkylidene complexes and to interfere unproductively with catalytic activity. Based on literature precedents, it has been established as a "dogma" that efficient metathesis reactions are suppressed in the presence of basic amines and that such substrates must invariably be deactivated by conversion of the amines to the corresponding carbamates or ammonium salts. However, an increasing number of examples of amine-containing compounds that are good substrates for metathesis is being reported in the literature. How can this "non-classical" reactivity be rationalized and exploited? The purpose of this review is to provide an overview of successful metathesis reactions performed with aminecontaining compounds in order to allow some guidelines to be formulated. A special emphasis is placed on the different parameters that may influence the outcome of the reaction such as steric effects, amine basicity, and the nature of the catalyst.

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Section: Ruthenium-catalyzed Metathesis Of Phenylamines and Analoguesmentioning

confidence: 99%

“…The higher reactivity of catalyst 3 was sufficient to overcome this difficulty and N-Boc-dihydroquinoline 101 was obtained in 97 % yield. [68] Secondary phenylamine 102 b was found to be a good partner in crossmetathesis reactions (Scheme 40).…”

Section: Ruthenium-catalyzed Metathesis Of Phenylamines and Analoguesmentioning

confidence: 99%

Olefin Metathesis of Amine‐Containing Systems: Beyond the Current Consensus

Compain¹

2007

Adv Synth Catal

162

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“…[59] It was found that the dihydroquinoline 110 was isolated in good yield following RCM, but that the protecting groups on nitrogen were removed during silica gel column chromatography and the resulting dihydroquinoline was spontaneously auto-oxidised to give 4-methylquinoline 111 directly.…”

Section: Construction Of Six-membered Aromatic Heterocyclesmentioning

confidence: 99%

Ring‐Closing Metathesis: Novel Routes to Aromatic Heterocycles

Donohoe

Fishlock

Procopiou

2008

Chemistry A European J

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Olefin metathesis has been established as an important and general reaction in synthetic organic chemistry. Recently, it has attracted interest as a powerful tool for the construction of aromatic heterocycles. The importance of heteroaromatic motifs in medicinal chemistry and biology, as well as the efficiency and wealth of metathesis transformations, have resulted in significant success in this rapidly developing area.

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“…For more than ten years, we have been exploring a synthetic methodology for nitrogen-containing heterocycles using these ruthenium carbene catalysts and applying them to the synthesis of biologically active natural products. [11][12][13][14][15][16][17][18][19][20][21][22][23][24][25][26][27][28][29][30] Here, we describe our synthetic study of nitrogen-containing heterocycles using ring-closing metathesis (RCM), such as chiral bicyclic lactams, azacycloundecenes, axially chiral macrolactams, 1,2-dihydroquinolines and indoles, including the development of silyl-enol ether ene metathesis and selective isomerization of terminal olefin, and its application to the synthesis of the natural products, (Ϫ)-coniceine, (S)-pyrrolam A and angustureine.…”

Section: Development Of Syntheticmentioning

confidence: 99%

“…Silyl enol ether-ene metathesis 16) : Many quinoline alkaloids which show important bioactivities, such as quinine and chloroquine, contain substituents at the 4-position. Therefore, we next focused our attention on extending this reaction to the synthesis of 4-substituted quinolines.…”

Section: Mitsuhiro Arisawa Was Born In 1971 Inmentioning

confidence: 99%

Development of Environmentally Benign Organometallic Catalysis for Drug Discovery and Its Application

Arisawa

2007

CHEMICAL & PHARMACEUTICAL BULLETIN

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We have developed a novel organometallic catalysis and applied it to drug discovery. Two new catalysts were found, ruthenium hydride with a nitrogen-containing heterocyclic carbene (A) and an organopalladium catalyst supported on a sulfur-terminated semiconductor, gallium arsenide (001) (B). Both catalysts are environmentally benign, because A can yield indole derivatives with good atom economy, and B can catalyze the Mizoroki-Heck reaction more than 10 times with only trace amounts of leached palladium (ppb level). We also describe our synthetic study of nitrogen-containing heterocycles using ring-closing metathesis (RCM), such as chiral bicyclic lactams, azacycloundecenes, axially chiral macrolactams, 1,2-dihydroquinolines and indoles, including the development of silyl-enol ether ene metathesis, selective isomerization of terminal olefin, enamide metathesis and cycloisomerization and its application to the syntheis of 4 natural products, (؊)-coniceine, (S)-pyrrolam A, angustureine, and fistulosin.

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Synthesis of substituted 1,2-dihydroquinolines and quinolines using ene–ene metathesis and ene–enol ether metathesis

Cited by 115 publications

References 13 publications

Olefin Metathesis of Amine‐Containing Systems: Beyond the Current Consensus

Olefin Metathesis of Amine‐Containing Systems: Beyond the Current Consensus

Ring‐Closing Metathesis: Novel Routes to Aromatic Heterocycles

Development of Environmentally Benign Organometallic Catalysis for Drug Discovery and Its Application

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