Elementorganic compounds with Si, P, As, B

Starck, B.

doi:10.1007/10201200_21

Cited by 2 publications

(2 citation statements)

References 16 publications

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“…However, for greater diversity, the heterocyclic ring needs to be constructed on variously substituted benzene rings. The heterocyclic ring is generally prepared by cyclocarbonylation of o -aminophenols with phosgene , or other carbonyl group donors, such as molten urea, ,,,, triphosgene, ,,,, aryl chloroformates, , carbonyl diimidazole, ,,,, etc. − Carbon monoxide has also been used for oxidative and reductive cyclocarbonylations of o -aminophenols and o -nitrophenols, respectively. Some examples of cyclization of o -hydroxyaryl isocyanates, generated in situ by Curtius, Schimdt, Hoffmann, , and Lossen , rearrangements of suitable salicylic acid derivatives, are also known.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 3-Alkylbenzoxazolones fromN-Alkyl-N-arylhydroxylamines by ContiguousO-Trichloroacetylation, Trichloroacetoxyortho-Shift, and Cyclization Sequence

Ram

Soni

2013

J. Org. Chem.

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Benzoxazolone pharmacophore is present in clinical pharmaceuticals, drug candidates, and many compounds having a wide spectrum of biological activities. The methods available for the synthesis of benzoxazolones have limited diversity due to problems in accessibility and air-sensitivity of diversely substituted o-aminophenols from which they are generally prepared by cyclocarbonylation with phosgene or its equivalents. The present paper describes a mild method for the synthesis of 3-alkylbenzoxazolones from easily accessible and air-stable nitroarenes. Nitroarenes were converted to N-alkyl-N-arylhydroxylamines in two steps involving partial reduction to arylhydroxylamines followed by selective N-alkylation. Treatment of N-alkyl-N-arylhydroxylamines with trichloroacetyl chloride and triethylamine afforded 3-alkylbenzoxazolones generally in good yields through an uninterrupted three-step sequence involving O-trichloroacetylation, N→C(ortho) trichloroacetoxy shift, and cyclization in a single pot at ambient temperatures. The present method is mild, wide in scope, economical, and regioselective. Many sensitive groups like alkyl and aryl esters, amide, cyano, and the carbon-carbon double bond survive the reaction.

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Section: Introductionmentioning

confidence: 99%

Synthesis of 3-Alkylbenzoxazolones fromN-Alkyl-N-arylhydroxylamines by ContiguousO-Trichloroacetylation, Trichloroacetoxyortho-Shift, and Cyclization Sequence

Ram

Soni

2013

J. Org. Chem.

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“…Reported values for the moments of inertia of HCl and DCl are respectively 2.68 x 10-40 and 5.19 x 10-40 g cm2 (Starck 1967).…”

Section: 1 Linear' Moleculesmentioning

confidence: 99%

Free rotational models for far-infrared absorptions of linear and symmetrical-top molecules dissolved in inert solvents

Morita

Calderwood

Walker

1976

J. Phys. D: Appl. Phys.

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Equations of rotational motion for rigid linear and symmetrical-top molecules which rotate without any interaction with the surrounding molecules are solved to obtain the dipole correlation function and the imaginary part of the complex permittivity of a non-interacting ensemble of such molecules. The calculated values of the absorption coefficients are compared with the experimental values obtained from far-infrared spectra of hydrogen chloride (a linear molecule) dissolved in various inert solvents, and of ammonia (a symmetrical-top molecule) dissolved in sulphur hexafluoride. For these comparisons, the far-infrared spectrum of hydrogen chloride dissolved in cyclohexane at 25 degrees C was measured, and other spectra were taken from the literature. The theoretically derived spectra were calculated using only reported values of moments of inertia.

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Elementorganic compounds with Si, P, As, B

Cited by 2 publications

References 16 publications

Synthesis of 3-Alkylbenzoxazolones fromN-Alkyl-N-arylhydroxylamines by ContiguousO-Trichloroacetylation, Trichloroacetoxyortho-Shift, and Cyclization Sequence

Synthesis of 3-Alkylbenzoxazolones fromN-Alkyl-N-arylhydroxylamines by ContiguousO-Trichloroacetylation, Trichloroacetoxyortho-Shift, and Cyclization Sequence

Free rotational models for far-infrared absorptions of linear and symmetrical-top molecules dissolved in inert solvents

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