Selective C-acylation of CH-active dicarbonyl compounds with ketenylidenetriphenylphosphorane: syntheses and structures of 3-phosphoranylideneacyltetronic acids, 3-phosphoranylideneacyl-4-oxocoumarins, and 4-phosphoranylideneacylpyrazol-5-ones

Schobert, Rainer; Siegfried, Sven; Nieuwenhuyzen, Mark; Milius, Wolfgang; Hampel, Frank

doi:10.1039/b001541p

Cited by 29 publications

(13 citation statements)

References 15 publications

(6 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The bond distances and angles in the title compound ( Fig. 1) agree very well with the corresponding bond distances and angles reported in a closely related compound (Schobert et al, 2000). In the title molecule, the central phosphorus atom adopts a tetrahedral geometry and is linked to three benzene rings and a planner coumarin moiety (maximum deviation of 0.005 (2) Å for C1 atom) via methylene carbonyl group.…”

Section: Data Collectionsupporting

confidence: 83%

See 1 more Smart Citation

3-[2-(Triphenylphosphanylidene)acetyl]-2H-chromen-2-one

et al. 2013

View full text Add to dashboard Cite

Key indicators: single-crystal X-ray study; T = 100 K; mean (C-C) = 0.002 Å; R factor = 0.035; wR factor = 0.093; data-to-parameter ratio = 13.7.In the title compound, C 29 H 21 O 3 P, a coumarin-substitued ylid, the P atom is linked to three benzene rings and a planar coumarin moiety via a methylenecarbonyl group. The bond lengths in the P C-C O fragment clearly indicate a delocalized system involving the olefinic and carbonyl bonds. The molecular structure is stabilized by an intramolecular C-HÁ Á ÁO interaction that results in an S7 graph-set ring motif. In the crystal, molecules are linked into a three-dimensional framework by C-HÁ Á ÁO hydrogen bonds. Related literature

show abstract

Section: Data Collectionsupporting

confidence: 83%

“…For applications and biological activity of coumarin, see: Kabak et al (1999); El-Ansary et al (1992); Czerpack & Skolska (1982); Reddy & Somayojulu (1981); Jund et al (1971). For the crystal structure of a related compound, see: Schobert et al (2000).…”

Section: Related Literaturementioning

confidence: 99%

3-[2-(Triphenylphosphanylidene)acetyl]-2H-chromen-2-one

et al. 2013

View full text Add to dashboard Cite

show abstract

“…Earlier, the synthesis of tetramates (and tetronates/thiotetronates) [80] incorporating the ylide Ph 3 PCCO 17 was published following the first paper on this methodology on tetronates in 1995 [81]. As reported by the same group, since tetramic and tetronic acids have acidic hydrogens at C-3, they can react with the same ylide 17 to give the corresponding 3-(triphenylphosphoranylidene) acetyl derivatives 18 [82], which were used toward the synthesis of ravenic acid 19 in 2010 (Scheme 5; Part B) [47].…”

Section: Involving Activated Cyclic Starting Materials or Intermediatesmentioning

confidence: 99%

Metal-Catalyzed and Metal-Mediated Approaches to the Synthesis and Functionalization of Tetramic Acids

Matiadis

2019

Catalysts

View full text Add to dashboard Cite

The heterocyclic ring of tetramic acids is found in naturally occurred biologically active products isolated from fungi, bacteria, molds, and sponges. Thus, these molecules have attracted significant attention as synthetic targets, and various synthetic paths have been developed. Over recent years, a growing number of catalytic approaches toward functionalized products have been established in order to overcome the limitations of the conventional methods. The present review describes the strategies for the metal-catalyzed and metal-promoted synthesis and further derivatization of tetramic acids, with emphasis on recent examples from the literature.

show abstract

“…Among the phosphorus compounds, the chemistry of phosphorus ylides is very significant in the chemistry of the twentieth century . Phosphorus ylides are reactive intermediates, which have been used in many reactions and are involved a lot in the synthesis of organic compounds . In continuation of our investigation on the organophosphorous synthesis by trivalent phosphorus nucleophiles and following the first report for the synthesis of C ‐amino phosphorous ylides by hexamethyl phosphorous triamide , we have recently described the synthesis of new phosphorous ylides from a reaction between hexamethyl phosphorous triamide and dimethyl acetylenedicarboxylate (DMAD) in the presence of N—H acids .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of New Stable Phosphorus Ylides and 1,4‐Diionic Organophosphorus Compound from a Reaction between Hexamethyl Phosphorous Triamide and Dimethyl Acetylenedicarboxylate in the Presence of CH‐Acids

Ziyaadini

Maghsoodlou

Hazeri

et al. 2012

Heteroatom Chemistry

View full text Add to dashboard Cite

A simple and efficient one‐pot three‐component reaction between hexamethyl phosphorous triamide and dimethyl acetylenedicarboxylate (DMAD) in the presence of CH‐acids, such as acetylacetone, 1,3‐indandione, dibenzoylmethane, anthrone, and N,N‐dimethylbarbituric acid, has been studied. In all cases, new and stable phosphorus ylides are obtained in excellent yields. These stable ylides exist in solution as a mixture of two geometrical isomers as a result of restricted rotation around the carbon–carbon partial double bond, resulting from conjugation of the ylide moiety with the adjacent carbonyl group. From the reaction of N,N‐dimethylbarbituric acid with DMAD in the presence of hexamethyl phosphorous triamide, a 1,4‐diionic organophosphorus compound is obtained. © 2012 Wiley Periodicals, Inc. Heteroatom Chem 24:84–89, 2013; View this article online at http://wileyonlinelibrary.com. DOI 10.1002/hc.21067

show abstract

Selective C-acylation of CH-active dicarbonyl compounds with ketenylidenetriphenylphosphorane: syntheses and structures of 3-phosphoranylideneacyltetronic acids, 3-phosphoranylideneacyl-4-oxocoumarins, and 4-phosphoranylideneacylpyrazol-5-ones

Cited by 29 publications

References 15 publications

3-[2-(Triphenylphosphanylidene)acetyl]-2H-chromen-2-one

3-[2-(Triphenylphosphanylidene)acetyl]-2H-chromen-2-one

Metal-Catalyzed and Metal-Mediated Approaches to the Synthesis and Functionalization of Tetramic Acids

Synthesis of New Stable Phosphorus Ylides and 1,4‐Diionic Organophosphorus Compound from a Reaction between Hexamethyl Phosphorous Triamide and Dimethyl Acetylenedicarboxylate in the Presence of CH‐Acids

Contact Info

Product

Resources

About