The Synthesis of Khellin Derivatives

Gardner, Thomas S.; Wenis, E.; Lee, John

doi:10.1021/jo01150a021

Cited by 20 publications

(2 citation statements)

References 6 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The following procedure for the preparation of 6-rt-butyl-7-hydroxy-4-methylcoumarin (I), exemplifies the general method for the preparation of the 6-alkyl-7hydroxy (and 7,8-dihydroxy) -4-methylcoumarins listed in Table I. 1 All melting-points were taken with Anschutz thermometers. A solution of 4-butylresorcinol (11.3 g., 0.068 mole) in ethyl acetoacetate (8.9 g., 0.068 mole) was added during 40 minutes to vigorously stirred 82% sulfuric acid (300 g., 183 ml.)…”

Section: Experimental•1mentioning

confidence: 99%

Some New Coumarins and Chromones and their Ultraviolet Absorption Spectra

Jacobson¹,

Brower²,

Amstutz³

1953

J. Org. Chem.

View full text Add to dashboard Cite

During the course of an investigation of phenolic compounds in this laboratory a series of thirteen new coumarins and four new chromones has been prepared and their ultraviolet absorption spectra have been recorded. The formulas for these compounds are given in Tables I and II and other pertinent data are assembled in Table III.These compounds have been prepared by standard methods and in most cases from known intermediates. The 6-alkyl-7-hydroxy-4-methylcoumarins (I and II) were obtained from resorcinol through the intermediate 4-alkylresorcinols which condensed with ethyl acetoacetate in 82% sulfuric acid to yield the coumarins. In the same way the 6-alkyl-7,8-dihydroxy-4-methylcoumarins (VI and VII) were prepared from pyrogallol through the intermediate 4-alkylpyrogallols. spectrophotometer using 95% ethanolic solutions at a concentration of 10 milligrams per liter. SUMMARYA series of thirteen new eonmarins and four new chromones has been prepared and their ultraviolet absorption spectra have been recorded. Bethlehem, Pa.

show abstract

Section: Experimental•1mentioning

confidence: 99%

Some New Coumarins and Chromones and their Ultraviolet Absorption Spectra

Jacobson¹,

Brower²,

Amstutz³

1953

J. Org. Chem.

View full text Add to dashboard Cite

show abstract

“…The di ( -carboxymethoxy) derivative (If) was obtained by acid hydrolysis of Ig. 6-Acetyl-3 (2H)-dihydro-3-ketokhellin has been synthesized from 2,5-dimethoxyresorcinol (I) (34,35). The latter compound on chloroacetylation gave 2,4-dihydroxy-3,6-dimethoxy-co-chloroacetophenone (II).…”

Section: Och Khellinmentioning

confidence: 99%

The Chemistry and the Physiological Action of Khellin and Related Products.

Huttrer¹,

Dale²

1951

Chem. Rev.

View full text Add to dashboard Cite

Hydrogenolysis of Benzyl Groups Attached to Oxygen, Nitrogen, or Sulfur

Hartung¹,

Simonoff²

2011

Organic Reactions

View full text Add to dashboard Cite

The benzyl group and a variety of substituted benzyl groups attached to an oxygen atom as in alcohols, ethers, acetals, or esters; to an amino nitrogen atom; or to a sulfur atom in thio ethers may be removed as toluene, or the corresponding substituted toluene, by hydrogenolysis. Other chemical and catalytic methods have been employed to bring about these debenzylations. It is the purpose of this chapter to give illustrations of both types of debenzylations so that their usefulness may be appreciated.

show abstract

The Synthesis of Khellin Derivatives

Cited by 20 publications

References 6 publications

Some New Coumarins and Chromones and their Ultraviolet Absorption Spectra

Some New Coumarins and Chromones and their Ultraviolet Absorption Spectra

The Chemistry and the Physiological Action of Khellin and Related Products.

Hydrogenolysis of Benzyl Groups Attached to Oxygen, Nitrogen, or Sulfur

Contact Info

Product

Resources

About