Synthese et structure d'amino-4 aza-2 dienes-1,3

Schoeni, Jean-Paul; Fleury, Jean‐Pierre

doi:10.1016/0040-4020(75)80069-x

Cited by 19 publications

(2 citation statements)

References 12 publications

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“…The acyliminium ion may alternatively be formed by direct nucleophilic attack of C10 of 3 at an sp 2 -hybridized nitrogen and substitution of the tosyloxy group. There is precedence for the bimolecular reaction of enamines with tosyloximes . A tosyloxime complex like 26 could be formed from reagent 3 and Ca 2+ liberated from CaO and traces of water.…”

Section: Resultsmentioning

confidence: 99%

Total Synthesis of the Cytostatic Marine Natural Product Dibromophakellstatin via Three-Component Imidazolidinone Anellation

2006

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The tetracyclic pyrrole-imidazole alkaloid dibromophakellstatin from the marine sponge Phakellia mauritiana has been synthesized within seven steps from pyrrole in an 18% overall yield. The key step is a three-component assembly of a tricyclic enamide, a nitrene, and a carbamoyl building block, affording the imidazolidinone ring of dibromophakellstatin in one step. Notably, it is possible to employ the reagent EtO2CNHOTs in a double function as a source of the electrophilic nitrene and of a dipolar carbamoyl component. Use of debrominated precursor dipyrrolopyrazinones leads to much higher anellation yields and allowed us to develop a second generation synthesis. The cytostatic activity of dibromophakellstatin is confirmed.

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Section: Resultsmentioning

confidence: 99%

Total Synthesis of the Cytostatic Marine Natural Product Dibromophakellstatin via Three-Component Imidazolidinone Anellation

2006

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“…The electronic nature of the R group has no apparent impact on the product yield under these conditions ( Table 1, entries [6][7][8][9][10][11][12][13][14][15][16]. When the R group increases the electrophilicity of a benzoyl chloride, it simultaneously decreases the nucleophilicity of the diacyl ketene-N,N¢-acetal intermediate, and vice versa.…”

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confidence: 99%

Tandem Reactions of 2-Methylimidazoline and 1,2-Dimethylimidazoline with Various Benzoyl Chlorides

Ye¹,

Chen²,

Chatterjee³

et al. 2009

Synthesis

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The reactions of 2-methylimidazoline with excess benzoyl chlorides under mild conditions generated N,N¢-diacyl-b-keto cyclic ketene-N,N¢-acetals. Conversely, the corresponding reactions of 1,2-dimethylimidazoline under the same conditions stereoselectively formed the ring-opened (Z)-vinyl benzoates. The latter reactions feature the formation of carbon-carbon bonds, carbonnitrogen bonds, and carbon-oxygen bonds in one sequential cascade.

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ChemInform Abstract: 2‐AZA‐DIENE‐(1,3) 1. MITT. SYNTHESE UND STRUKTUR VON 4‐AMINO‐2‐AZA‐DIENEN‐(1,3)

Schoeni¹,

Fleury²

1975

Chemischer Informationsdienst

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Synthese et structure d'amino-4 aza-2 dienes-1,3

Cited by 19 publications

References 12 publications

Total Synthesis of the Cytostatic Marine Natural Product Dibromophakellstatin via Three-Component Imidazolidinone Anellation

Total Synthesis of the Cytostatic Marine Natural Product Dibromophakellstatin via Three-Component Imidazolidinone Anellation

Tandem Reactions of 2-Methylimidazoline and 1,2-Dimethylimidazoline with Various Benzoyl Chlorides

ChemInform Abstract: 2‐AZA‐DIENE‐(1,3) 1. MITT. SYNTHESE UND STRUKTUR VON 4‐AMINO‐2‐AZA‐DIENEN‐(1,3)

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