Pyrroles from ketoximes and acetylene. 22. Dihaloethanes in place of acetylene in reactions with cyclohexanone oxime

Михалева, А. И.; Трофимов, Б. А.; Vasil'ev, A. N.; Komarova, G. A.; Skorobogatova, V. I.

doi:10.1007/bf00513432

Cited by 6 publications

(4 citation statements)

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“…Melting points are uncorrected. p -Acetamidobenzenesulfonyl azide ( p -ABSA), the chiral rhodium prolinate catalyst 2 ,8c vinyl diazomethanes 3 , 19a ,9b 19b ,9b N -(methoxycarbonyl)pyrrole, N -acetylpyrrole, N -(methanesulfonyl)pyrrole, 2-phenylpyrrole, 2,5-dimethyl-1-[(1,1-dimethylethoxy)carbonyl]pyrrole ( 4f ), and 4,5,6,7-tetrahydroindole ( 4h ) 23 were prepared by literature procedures. 2-Methyl and 3-methylpyrrole were prepared from the corresponding carboxaldehydes via Wolff−Kishner reduction. , Unless otherwise stated, enantiomeric excesses of the [3.2.1] ring systems were determined by gas chromatography on a permethylated β-cyclodextrin (β-PH) column obtained from Astec Separations connected to a Hewlett-Packard 5890 Series II Plus gas chromatograph.…”

Section: Methodsmentioning

confidence: 99%

“…Melting points are uncorrected. p-Acetamidobenzenesulfonyl azide (p-ABSA), 11 the chiral rhodium prolinate catalyst 2, 8c vinyl diazomethanes 3, 7 19a, 9b 19b, 9b N-(methoxycarbonyl)pyrrole, 20 N-acetylpyrrole, 21 N-(methanesulfonyl)pyrrole, 22 2-phenylpyrrole, 23 2,5dimethyl-1-[(1,1-dimethylethoxy)carbonyl]pyrrole (4f), 24 and 4,5,6,7-tetrahydroindole (4h) 23 were prepared by literature procedures. 2-Methyl and 3-methylpyrrole were prepared from the corresponding carboxaldehydes via Wolff-Kishner reduction.…”

Section: Methodsmentioning

confidence: 99%

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Enantioselective Synthesis of Functionalized Tropanes by Rhodium(II) Carboxylate-Catalyzed Decomposition of Vinyldiazomethanes in the Presence of Pyrroles

et al. 1997

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A series of enantiomerically enriched tropanes was synthesized by the rhodium(II) octanoatecatalyzed reaction of various N-BOC-protected pyrroles with vinyldiazomethanes. The overall 3 + 4 annulation occurs by a tandem cyclopropanation/Cope rearrangement. Asymmetric induction was best achieved in these transformations by using either (S)-lactate or (R)-pantolactone as a chiral auxiliary on the vinyldiazomethanes. Reactions carried out with the chiral catalyst tetrakis-[N-(4-tert-butylbenzenesulfonyl)-(L)-prolinato]dirhodium (2) provided moderate asymmetric induction, but also resulted in the formation of isomeric azabicyclooctane side products. The utility of the synthetic process was demonstrated through the asymmetric synthesis of (-)-anhydroecgonine methyl ester and (-)-ferruginine.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Enantioselective Synthesis of Functionalized Tropanes by Rhodium(II) Carboxylate-Catalyzed Decomposition of Vinyldiazomethanes in the Presence of Pyrroles

et al. 1997

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“…In place of acetylene it is possible to use its synthetic equivalents -vinyl halides [86,121,122] and 1,2-dihaloethanes [123][124][125] and also a propyne-allene mixture [126]. Pyrroles with alkyl, cycloalkyl, aryl, and hetaryl substituents and also pyrroles annulated with carbocycles and condensed systems have become accessible [87,94,95,118] as a result of this reaction, known as the Trofimov reaction (e.g., see [97,129] and the references therein).…”

mentioning

confidence: 99%

Chemistry of heterocyclic compounds at the A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, over 50 years (Review)

Nedolya

2008

Chem Heterocycl Comp

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“…Starting from carboxylic acid 7 , Weinreb-amide 8 and ketone 9 were obtained in two steps, consecutively. Afterwards, oxime 10 was synthesized to be used as starting material in the Trofimov pyrrole synthesis toward pyrrole 11a , as previously described ( Mikhaleva et al, 1981 ; Trofimov et al, 2015 ; Klein et al, 2018 ). The Trofimov pyrrole synthesis represents the yield-limiting step in this synthesis sequence ( Figure 3 ).…”

Section: Resultsmentioning

confidence: 99%

Production of tailored hydroxylated prodiginine showing combinatorial activity with rhamnolipids against plant-parasitic nematodes

Kossmann,

Huang,

Weihmann

et al. 2023

Front. Microbiol.

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Bacterial secondary metabolites exhibit diverse remarkable bioactivities and are thus the subject of study for different applications. Recently, the individual effectiveness of tripyrrolic prodiginines and rhamnolipids against the plant-parasitic nematode Heterodera schachtii, which causes tremendous losses in crop plants, was described. Notably, rhamnolipid production in engineered Pseudomonas putida strains has already reached industrial implementation. However, the non-natural hydroxyl-decorated prodiginines, which are of particular interest in this study due to a previously described particularly good plant compatibility and low toxicity, are not as readily accessible. In the present study, a new effective hybrid synthetic route was established. This included the engineering of a novel P. putida strain to provide enhanced levels of a bipyrrole precursor and an optimization of mutasynthesis, i.e., the conversion of chemically synthesized and supplemented monopyrroles to tripyrrolic compounds. Subsequent semisynthesis provided the hydroxylated prodiginine. The prodiginines caused reduced infectiousness of H. schachtii for Arabidopsis thaliana plants resulting from impaired motility and stylet thrusting, providing the first insights on the mode of action in this context. Furthermore, the combined application with rhamnolipids was assessed for the first time and found to be more effective against nematode parasitism than the individual compounds. To obtain, for instance, 50% nematode control, it was sufficient to apply 7.8 μM hydroxylated prodiginine together with 0.7 μg/ml (~ 1.1 μM) di-rhamnolipids, which corresponded to ca. ¼ of the individual EC50 values. In summary, a hybrid synthetic route toward a hydroxylated prodiginine was established and its effects and combinatorial activity with rhamnolipids on plant-parasitic nematode H. schachtii are presented, demonstrating potential application as antinematodal agents. Graphical Abstract

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Pyrroles from ketoximes and acetylene. 22. Dihaloethanes in place of acetylene in reactions with cyclohexanone oxime

Cited by 6 publications

References 0 publications

Enantioselective Synthesis of Functionalized Tropanes by Rhodium(II) Carboxylate-Catalyzed Decomposition of Vinyldiazomethanes in the Presence of Pyrroles

Enantioselective Synthesis of Functionalized Tropanes by Rhodium(II) Carboxylate-Catalyzed Decomposition of Vinyldiazomethanes in the Presence of Pyrroles

Chemistry of heterocyclic compounds at the A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, over 50 years (Review)

Production of tailored hydroxylated prodiginine showing combinatorial activity with rhamnolipids against plant-parasitic nematodes

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