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Knölker, Hans‐Joachim; Baum, Gerhard; Foitzik, Norbert; Goesmann, Helmut; Gonser, Peter; Jones, Peter G.; Röttele, Herbert

doi:10.1002/(sici)1099-0682(199807)1998:7<993::aid-ejic993>3.3.co;2-y

Cited by 27 publications

(70 citation statements)

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“…9,10 The addition of 3-trimethylsilylpropargylmagnesium bromide (4) requires an activation of the aldimines 3. Following Nakagawa's procedure by generation of a preformed aldimine-BF 3 complex, 11 the homopropargylamines 5a-c were available in yields ranging from 78-88%.…”

Section: Resultsmentioning

confidence: 99%

“…Yellow-green crystals; for spectroscopic data, see ref. 10 General procedure for the synthesis of the homopropargylamines 5a-c. Boron trifluoridediethyl ether complex (8.0 mmol) is added to a solution of the Schiff bases 3a-c (8.0 mmol) in THF at -23 °C. After stirring for 30 min, a solution of freshly prepared 3-trimethylsilylpropargylmagnesium bromide (4) (24 mmol) in diethyl ether is added dropwise to this suspension.…”

Section: -Methoxy-n-[(e)-3-phenylallylidene]aniline (3c)mentioning

confidence: 99%

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Transition metals in organic synthesis, Part 105. Synthesis of pyrroles by silver(I)-promoted oxidative cyclization

Agarwal¹,

Pässler²,

Knölker³

2012

Arkivoc

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Section: Resultsmentioning

confidence: 99%

Section: -Methoxy-n-[(e)-3-phenylallylidene]aniline (3c)mentioning

confidence: 99%

Transition metals in organic synthesis, Part 105. Synthesis of pyrroles by silver(I)-promoted oxidative cyclization

Agarwal¹,

Pässler²,

Knölker³

2012

Arkivoc

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“…Coordination of cyclohexadienes to the tricarbonyliron fragment is most efficiently achieved by the 1-azadiene-catalyzed complexation developed in our laboratories. [8][9][10] Thus, catalytic complexation of cyclohexa-1,3-diene (3) with pentacarbonyliron quantitatively provides tricarbonyl( 4 -cyclohexa-1,3-diene)iron (6). It is important to note that this process can be applied as well to substituted cyclohexadienes leading to the corresponding substituted irondiene complexes.…”

Section: ç Iron-mediated Synthesis Of Carbazolesmentioning

confidence: 99%

“…10,11 Subsequent hydride abstraction affords the tricarbonyliron-coordinated cyclohexadienylium salt 7 (Scheme 2). 8,12 The tricarbonyliron-coordinated cations are useful electrophiles for regioselective electrophilic aromatic substitution of arylamines. This reactivity is exploited to construct the central C-C bond of the carbazole framework.…”

Section: ç Iron-mediated Synthesis Of Carbazolesmentioning

confidence: 99%

Synthesis of Biologically Active Carbazole Alkaloids Using Selective Transition-metal-catalyzed Coupling Reactions

Knölker¹

2008

Chemistry Letters

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Highly convergent syntheses of substituted carbazoles are most conveniently achieved using organometallic chemistry. Construction of the carbazole framework via the iron-mediated route proceeds by a sequence of C-C and C-N bond formation. In the highly efficient palladium-catalyzed route the C-N bond is formed first followed by generation of the C-C bond. This article highlights some recent developments and applications to the total synthesis of biologically active carbazole alkaloids. Ç IntroductionThe chemistry and biology of carbazole alkaloids has attracted an increasing interest over the last 50 years. Important milestones for the tremendous development of this class of natural products were the isolation of ellipticine (1) Since then a broad range of structurally interesting carbazole alkaloids with useful biological activities has been isolated from diverse natural sources.3,4 The pharmacological potential of these natural products initiated the development of novel synthetic methods for efficient routes to carbazoles. 4 We have established an iron-mediated and a palladium-catalyzed route, which are based on transition metal-induced coupling reactions of arylamines. 5 The present article briefly summarizes these achievements and shows recent applications to total synthesis.

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“…All reactions were carried out under nitrogen, but no precautions to exclude air were taken during work-up. 4 The azabutadiene 4-phenyl-1-p-tolyl-1-azabuta-1,3-diene 3a, its 1,4-diphenyl analogue and PhCH 2 Mn(CO) 5 were prepared by literature routes [20,21]. PLC and TLC refer to preparative and thin layer chromatography on silica gel (Merck Kieselgel 60 PF 254 ).…”

Section: Generalmentioning

confidence: 99%

Manganese carbonyl-mediated reactions of azabutadienes with phenylacetylene, methyl acrylate and other unsaturated molecules

Mace¹,

Main²,

Nicholson³

et al. 2004

Journal of Organometallic Chemistry

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SynopsisPhCH 2 Mn(CO) 5 reacts with 1,4-di-aryl-1-aza-1,3-butadienes in the presence of unsaturated substrates to give products based on a cyclomanganated intermediate.PhCH 2 Mn(CO) 5PhC CH PhNCO CH 2 =CHCOOMe CO 2 Abstract.Reaction of PhCH 2 Mn(CO) 5 with 1,4-di-aryl-1-aza-1,3-butadienes gave substituted pyrrolinonyl rings which were 4 -coordinated to a Mn(CO) 3 group. These are formed by intramolecular CO insertion into a (non-isolated) cyclomanganated intermediate, followed by cyclisation. Other unsaturated reagents (PhC>CH, CH 2 =CHCOOMe, PhNCO) gave products arising from insertion of these, including a structurally characterised tri-aryl-5 -azacyclohexadienyl-Mn(CO) 3 complex from the reaction with the alkyne.

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Cited by 27 publications

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Transition metals in organic synthesis, Part 105. Synthesis of pyrroles by silver(I)-promoted oxidative cyclization

Transition metals in organic synthesis, Part 105. Synthesis of pyrroles by silver(I)-promoted oxidative cyclization

Synthesis of Biologically Active Carbazole Alkaloids Using Selective Transition-metal-catalyzed Coupling Reactions

Manganese carbonyl-mediated reactions of azabutadienes with phenylacetylene, methyl acrylate and other unsaturated molecules

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