Synthese von chinoxalin- und indol-2,3-dicarbonsäureimiden

Augustin, M.; Köhler, Manfred; Faust, Jürgen; Al-Holly, M. M.

doi:10.1016/0040-4020(80)80077-9

Cited by 9 publications

(3 citation statements)

References 6 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The MeOH extract derived from a solid fermentation of P. citrinum (MST-F10130) was concentrated in vacuo and the residue fractionated by repeated reverse phase SPE and HPLC to yield the known P. citrinum metabolites, quinolactacins 1-4, together with the new quinolactacins B1 (5), C1 (6), D1 (7) and D2 (8), and the novel derivatives quinolonimide (9) and quinolonic acid (10).…”

Section: Resultsmentioning

confidence: 99%

“…As part of our research into the chemistry of Australian microorganisms we investigated a P. citrinum strain (MST-F10130) isolated from an Australian soil sample. The solid phase fermentation of this fungus led to the isolation and identification of the known quinolactacins A2, B2, C2 and A1 (1)(2)(3)(4), as well as the new quinolactacins B1 (5), C1 (6), D1 (7) and D2 (8), and the novel analogues quinolonimide (9) and quinolonic acid (10). Careful analysis of the quinolactacins revealed that all were unstable and engaged in a sequence of decomposition transformations that ultimately led to quinolonimide (9), and from there to quinolonic acid (10).…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Quinolactacins revisited: from lactams to imide and beyond

Clark

Capon

Lacey³

et al. 2006

Org. Biomol. Chem.

View full text Add to dashboard Cite

Chemical analysis of a solid phase fermentation of an Australian Penicillium citrinum strain has returned all known examples of a rare class of N-methyl quinolone lactams, quinolactacins A2 (1), B2 (2), C2 (3) and A1 (4), together with the new quinolactacins B1 (5), C1 (6), D1 (7) and D2 (8), and the novel derivatives quinolonimide (9) and quinolonic acid (10). Complete stereostructures were assigned to all these compounds by detailed spectroscopic analysis and chemical interconversion. Carefully controlled and monitored decomposition studies have confirmed that quinolactacins readily undergo C-3 epimerization and oxidation, and under appropriate conditions convert to quinolonimide and quinolonic acid. Mechanisms for key transformations are proposed. The decomposition studies suggested that only quinolactacins A2 (1) and B2 (2) are genuine natural products, with all other isolated compounds being decomposition artefacts. Quinolactacins C1 (6), C2 (3), and the racemic mixture of quinolactacins D1/D2 (8/7) all displayed notable cytotoxic activity.

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Quinolactacins revisited: from lactams to imide and beyond

Clark

Capon

Lacey³

et al. 2006

Org. Biomol. Chem.

View full text Add to dashboard Cite

show abstract

“…Longer reaction times (1−2 h) led to formation of imide 5a quantitatively. Although direct conversions of phthalic acids or phthalimides to diamides via treatment with amines are known, in the case of diacid 2 and imide 5a , we did not obtain satisfactory results. Treatment of diacid 2 or monoamide 4 with DCC and p- anisidine afforded a complex mixture with no traces of diamide 3 .…”

mentioning

confidence: 99%

Overcoming Regioselectivity Issues Inherent in Bis-Tröger's Base Preparation

2006

View full text Add to dashboard Cite

[structure: see text] Bis-Tröger's base derivatives are a new family of molecular tweezers. A major drawback to their study is a lack of commercially available precursors, ortho-nitrocarboxylic acids. A reverse synthetic strategy starting from known dinitrodicarboxylic acids, which circumvents this problem, is presented. Via this methodology regioisomeric bis-TB derivatives can be prepared selectively, using only common aromatic amines that are typically commercially available.

show abstract

Cyclization of Vinyl and Aryl Azides into Pyrroles, Indoles, Carbazoles, and Related Fused Pyrroles

Berkowitz

McCombie

2017

Organic Reactions

View full text Add to dashboard Cite

This chapter reviews in detail those reactions that form of a new pyrrole ring from vinyl, aryl, and heteroaryl azides via formal C–H insertion processes under thermal, photochemical, and metal‐catalyzed conditions. These reactions proceed via the intermediacy of vinyl or aryl nitrenes (or their metallonitrene equivalents) and generate a wide variety of pyrroles, indoles, carbazoles, and related systems. Methods for the synthesis of the starting azides are summarized, and a comprehensive survey of the cyclization processes is provided.

show abstract

Synthese von chinoxalin- und indol-2,3-dicarbonsäureimiden

Cited by 9 publications

References 6 publications

Quinolactacins revisited: from lactams to imide and beyond

Quinolactacins revisited: from lactams to imide and beyond

Overcoming Regioselectivity Issues Inherent in Bis-Tröger's Base Preparation

Cyclization of Vinyl and Aryl Azides into Pyrroles, Indoles, Carbazoles, and Related Fused Pyrroles

Contact Info

Product

Resources

About