- 1,3-Dipolar Cycloaddition of Nitrones with Nitriles. Scope and Mechanistic Study
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1,3-Dipolar cycloadditions of nitrones 1-6 with nitriles 14-16, proceeded under thermal as well as under high pressure conditions with complete regioselectivity to give Δ4-1,2,4-oxadiazolines 17-19.In general, the cycloaddition seemed to be controlled by a HOMO(nitrone)- LUMO(nitrile) interaction.However, a crossover in the orbital control is probable observed with nitrile 16c.Nitrone-nitrile cycloadditions are normal type II cycloadditions so that the nitriles have a U-shaped reactivity curve.Kinetic study on solvent polarity and Hammett equation demonstrated that mechanistically the nitrone-nitrile cycloaddition is consistent with nitrone-alkene cycloaddition.
- Hermkens, Pedro H.H.,Maarseveen, Jan H. v.,Kruse, Chris G.,Scheeren, Hans W.
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p. 6491 - 6504
(2007/10/02)
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- Employment of Nitriles in the Stereoselective Cycloaddition to Nitrones
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The cycloaddition of the nitrones 8-11 to the geminal dinitriles 12a-d has been evaluated.Under thermal as well high-pressure reaction conditions 1,3 dipolar cycloadditions proceed with complete regioselectivity to give the Δ4-1,2,4-oxadiazolin
- Plate, Ralf,Hermkens, Pedro H. H.,Smits, Jan M. M.,Nivard, Rutger J. F.,Ottenheijm, Haary C. J.
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p. 1047 - 1051
(2007/10/02)
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- AROMATIZATION OF 3,4-DIHYDRO-β-CARBOLINE-3-CARBOXYLIC ACID AND ITS DERIVATIVES THROUGH A CARBANION INTERMEDIATE : MECHANISTIC STUDY AND USE IN CHEMICAL SYNTHESIS
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3,4-dihydro-β-carboline-3-carboxylic acid, its esters and amide derivatives (AH2) undergo complete aromatization into corresponding β-carboline derivatives (A) by basic treatment under mild conditions.This, together with the easy obtention of 3,4-dihydro-
- Previero, A.,Barry, L-G.,Torreilles, J.,Fleury, B.,Letellier, S.,Maupas, B.
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p. 221 - 234
(2007/10/02)
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- β-Carbolin-3-carboxylic acid derivatives
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A β-carbolin-3-carboxylic acid derivative of the formula STR1 has valuable pharmacological properties when administered to patients, e.g. humans as a drug, have been shown to possess interesting tranquilizing activity.
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