Magnesium Perchlorate

Chakraborti, Asit K.; Chankeshwara, Sunay V.

doi:10.1002/047084289x.rn01002

Cited by 2 publications

(2 citation statements)

References 108 publications

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“…Our previous work on the catalytic synthesis of spiro[4 H -pyran-oxindole] derivatives was carried out smoothly in the presence of magnesium perchlorate [ 26 ]. The handling, storage, and precautionary information of the oxidative Mg(ClO 4 ) 2 can be found in the literature, and it is relatively safe when used as a Lewis acid catalyst [ 27 , 28 ].…”

Section: Introductionmentioning

confidence: 99%

An Efficient Synthesis of Spiro[indoline-3,9′-xanthene]trione Derivatives Catalyzed by Magnesium Perchlorate

Chen

Liang

et al. 2017

Molecules

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A simple and efficient method for the synthesis of spiro[indoline-3,9′-xanthene]trione derivatives by means of condensation between isatins and 1,3-cyclohexanedione in the presence of a catalytic amount of magnesium perchlorate at 80 °C in 50% aqueous ethanol medium has been described. Notably, the present method offers desirable advantages of good yields, simplicity of workup procedure, easy purification, and reduced reaction times.

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Section: Introductionmentioning

confidence: 99%

An Efficient Synthesis of Spiro[indoline-3,9′-xanthene]trione Derivatives Catalyzed by Magnesium Perchlorate

Chen

Liang

et al. 2017

Molecules

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“…However, metal triflimidates are costly, only a few triflimidates are commercially available, and their preparation require additional efforts and costly reagents. These drew our attention toward metal perchlorates to develop Zn(ClO 4 ) 2 · x H 2 O-catalyzed opening of the epoxide ring by amines . However, the reactions with aliphatic amines required heating .…”

Section: Introductionmentioning

confidence: 99%

Zinc Tetrafluoroborate Hydrate as a Mild Catalyst for Epoxide Ring Opening with Amines: Scope and Limitations of Metal Tetrafluoroborates and Applications in the Synthesis of Antihypertensive Drugs (RS)/(R)/(S)-Metoprolols

2011

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The scope and limitations of metal tetrafluoroborates have been studied for epoxide ring-opening reaction with amines, and Zn(BF(4))(2)·xH(2)O has been found to be a mild and efficient catalyst affording high yields under solvent-free conditions at rt with excellent chemo-, regio-, and stereoselectivities. The catalytic efficiency followed the order Zn(BF(4))(2)·xH(2)O ≫ Cu(BF(4))(2)·xH(2)O > Co(BF(4))(2)·6H(2)O ≫ Fe(BF(4))(2)·6H(2)O > LiBF(4) for reactions with cyclohexene oxide and Zn(BF(4))(2)·xH(2)O ≫ Co(BF(4))(2)·6H(2)O ≫ Fe(BF(4))(2)·6H(2)O > Cu(BF(4))(2)·xH(2)O for stilbene oxide, but AgBF(4) was ineffective. For reaction of styrene oxide with aniline, the metal tetrafluoroborates exhibited comparable regioselectivity (1:99-7:93) with preferential reaction at the benzylic carbon of the epoxide ring. A reversal of regioselectivity (91:1-69:31) in favor of the reaction at the terminal carbon of the epoxide ring was observed for reaction with morpholine. The regioselectivity was dependent on the electronic and steric factors of the epoxide and the pK(a) of the amine and independent of amine nucleophilicity. The role of the metal tetrafluoroborates is envisaged as "electrophile nucleophile dual activation" through cooperativity of coordination, charge-charge interaction, and hydrogen-bond formation that rationalizes the catalytic efficiency, substrate reactivity, and regioselectivity. The methodology was used for synthesis of cardiovascular drug metoprolol as racemic and enriched enantiomeric forms.

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Magnesium Perchlorate

Cited by 2 publications

References 108 publications

An Efficient Synthesis of Spiro[indoline-3,9′-xanthene]trione Derivatives Catalyzed by Magnesium Perchlorate

An Efficient Synthesis of Spiro[indoline-3,9′-xanthene]trione Derivatives Catalyzed by Magnesium Perchlorate

Zinc Tetrafluoroborate Hydrate as a Mild Catalyst for Epoxide Ring Opening with Amines: Scope and Limitations of Metal Tetrafluoroborates and Applications in the Synthesis of Antihypertensive Drugs (RS)/(R)/(S)-Metoprolols

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