Stereospecificity of Diels–Alder Reactions Validated Using Ab Initio Calculations: Synthesis of Novel Coumarin and Phenanthridine Derivatives

El‐Shafei, Ahmed; Fadda, Ahmed A.; Abdel-Gawad, I. I.; Youssif, E. H. E.

doi:10.1080/00397910802711326

Cited by 15 publications

(10 citation statements)

References 14 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The reaction of 4‐styrylcoumarins with styrene, allyl bromide, and ethyl acrylate in dichloromethane at room temperature is reported to furnish the corresponding Diels–Alder adducts . However, the reaction failed in our hands.…”

Section: Resultsmentioning

confidence: 83%

“…However, the reaction failed in our hands. The products having structure such as 3 , with the surviving double bond exocyclic to the B ring, are reported to be formed in the reaction . This product seems to be less likely when the reaction is carried out in a polar solvent at a high temperature.…”

Section: Resultsmentioning

confidence: 99%

“…In our efforts to use the 3,4 double bond in 3,4 annulation of coumarins, we undertook a detailed investigation of the Diels–Alder reaction of 4‐styrylcoumarins. In the first report on this reaction, position of the surviving double bond (in ring “C”) was not established unambiguously , and the subsequent workers maintained the same position . We felt that placement of the surviving double bond in the C ring was less favorable than in the B ring.…”

Section: Introductionmentioning

confidence: 94%

“…These reactions require long reaction time. Recently, 4‐styrylcoumarins have been prepared by the condensation of 4‐methylcoumarin with benzaldehydes in the presence of catalytic amount of piperidine . 4‐Styrylcoumarin thus prepared is reported to react with different dienophiles in dichloromethane at room temperature to form the corresponding adducts.…”

Section: Introductionmentioning

confidence: 99%

“…4‐Styrylcoumarin thus prepared is reported to react with different dienophiles in dichloromethane at room temperature to form the corresponding adducts. On the basis of ab initio calculations at the Hartree‐Fock level using the basis set 6–31 G (d, p), the reaction has been shown to follow normal electron demand pathway and the endo adduct is found to be thermodynamically and kinetically more favorable than the exo adduct .…”

Section: Introductionmentioning

confidence: 99%

See 4 more Smart Citations

Investigation of Diels-Alder Reaction of 7-Substituted 4-Styrylcoumarins with Symmetrical Dienophiles Leading to 3,4-Annulated Coumarins

Sanap

Kulkarni

Samant

2013

J. Heterocyclic Chem.

View full text Add to dashboard Cite

Section: Resultsmentioning

confidence: 83%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 94%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Investigation of Diels-Alder Reaction of 7-Substituted 4-Styrylcoumarins with Symmetrical Dienophiles Leading to 3,4-Annulated Coumarins

Sanap

Kulkarni

Samant

2013

J. Heterocyclic Chem.

View full text Add to dashboard Cite

Synthesis, computational and antimicrobial evaluation of some new pyridine derivatives

Alsoliemy

2022

Archiv der Pharmazie

View full text Add to dashboard Cite

A series of pyridine compounds were prepared by using 3‐(dimethylamino)‐1‐(pyridin‐4‐yl)prop‐2‐en‐1‐one (14) as a precursor. The reaction of 14 with different reagents afforded different new heterocyclic compounds. All the new compounds were characterized by spectroscopic analyses. Moreover, the density function theory study was made to establish the geometry of the tested compounds. The antimicrobial activities of the newly prepared pyridine derivatives were studied against Gram‐positive bacteria (Bacillus subtilis and Bacillus thuringiensis) and Gram‐negative bacteria (Escherichia coli and Pseudomonas aeruginosa) and fungi (Fusarium oxysporum and Botrytis fabae) by the minimal inhibitory concentration method. Compounds belonging to the pyran 32, pyridine 33, indenopyran 34, thiazolopyridine 35, and chromene 39 series displayed a high antimicrobial activity. It was found that the experimental results of the biological evaluation were in agreement with the molecular modeling studies.

show abstract

ChemInform Abstract: Stereospecificity of Diels—Alder Reactions Validated Using ab initio Calculations: Synthesis of Novel Coumarin and Phenanthridine Derivatives.

et al. 2010

View full text Add to dashboard Cite

show abstract

Stereospecificity of Diels–Alder Reactions Validated Using Ab Initio Calculations: Synthesis of Novel Coumarin and Phenanthridine Derivatives

Cited by 15 publications

References 14 publications

Investigation of Diels-Alder Reaction of 7-Substituted 4-Styrylcoumarins with Symmetrical Dienophiles Leading to 3,4-Annulated Coumarins

Investigation of Diels-Alder Reaction of 7-Substituted 4-Styrylcoumarins with Symmetrical Dienophiles Leading to 3,4-Annulated Coumarins

Synthesis, computational and antimicrobial evaluation of some new pyridine derivatives

ChemInform Abstract: Stereospecificity of Diels—Alder Reactions Validated Using ab initio Calculations: Synthesis of Novel Coumarin and Phenanthridine Derivatives.

Contact Info

Product

Resources

About