The Synthesis of α-Amino-o-tolualdehyde Diethylacetal and its Attempted Conversion to Pseudoisoindole

Börnstein, J.; Bedell, S. F.; Drummond, P. E.; Kosloski, Clement L.

doi:10.1021/ja01582a026

Cited by 49 publications

(25 citation statements)

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“…2 Because of the versatility and usefulness of acetals in organic synthesis, several methods for the protection [3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20] and the selective, mild deprotection 21 of aldehydes and ketones have been described. The classical procedure for protection involves the Lewis [3][4][5][6][7][8][9][10][11][12][13][14][15] or protic acid-catalyzed [16][17][18][19][20] reaction of a carbonyl compound with a large excess of an alcohol in the presence of a water scavenger. Among the employed Lewis acids are metal triflates, [3][4][5][6][7][8] 19 and silica-supported HClO 4 20 have been used as protic acids.…”

Section: Introductionmentioning

confidence: 99%

The use of anhydrous CeCl3 as a recyclable and selective catalyst for the acetalization of aldehydes and ketones

Silveira¹,

Mendes²,

Ziembowicz³

et al. 2010

J. Braz. Chem. Soc.

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Um método eficiente, limpo, quimiosseletivo e sem a utilização de solventes para a síntese de dimetil acetais de aldeídos e cetonas foi desenvolvido usando ortoformiato de trimetila e CeCl 3 anidro como catalisador. O método é geral e, sob condições reacionais brandas, fornece compostos carbonílicos protegidos em bons rendimentos, incluindo aril e alquil cetonas e aldeídos. O catalisador pode ser reutilizado diretamente, três vezes, sem perda significativa da atividade.An efficient, clean, chemoselective and solvent-free method for the synthesis of ketone and aldehyde dimethyl acetals was developed using trimethyl orthoformate and commercially available anhydrous CeCl 3 as a recyclable catalyst. The method is general and affords the protected carbonyl compounds in good yields and under mild conditions, including aryl and alkyl ketones and activated aldehydes. The catalyst could be utilised directly for 3 cycles, without significant loss of activity.

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Section: Introductionmentioning

confidence: 99%

The use of anhydrous CeCl3 as a recyclable and selective catalyst for the acetalization of aldehydes and ketones

Silveira¹,

Mendes²,

Ziembowicz³

et al. 2010

J. Braz. Chem. Soc.

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“…The commonly used acid catalysts include corrosive protic acids such as HCI, H 2S04 and Lewis acids such as ZnCl 2 and FeCI J [18,19]. Homogeneous acid catalysts ranging from Mg(C10 4h[20j, p-toluenesulphonic acid [21], and a series of cationic diphosphine Lewis acidic complexes of Pt(lI), Pd(II), and Rh(llI) [22,23], etc.…”

Section: Introductioñmentioning

confidence: 99%

Synthesis of dimethyl acetal of ketones: design of solid acid catalysts for one-pot acetalization reaction

Thomas

Prathapan

Sugunan

2005

Microporous and Mesoporous Materials

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The synthesis of dimethyl acctals of carbonyl compounds such as cyclohcxanone, acetophenone, and bcnzophenone has successfully been carried out by the reaction between ketones and methanol using different solid acid catalysts. The strong influence of the · textural properties of the catalysts such as acid amount and adsorption properties (surface area and pore volume) determine thẽ catalytic activity. The molecular size of the reactants and products determine the acetalization ability of a particular ketone. The

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“…The commonly used acid catalysts include corrosive protic acids such as HCl, H 2 SO 4 and Lewis acids such as ZnCl 2 and FeCl 3 [23,24]. A series of diphosphine complexes have also been employed for the synthesis of acetals [25,26].…”

Section: Introductionmentioning

confidence: 99%

Acetalation of Pentaerithritol Catalyzed by an Al-Pillared Saponite

et al. 2011

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Acetalation of pentaerithritol has been carried out in the presence of an Al-pillared saponite. Several carbonyl compounds were used, including aldehydes and ketones. Yields between 72 and 93% were obtained in all cases, except in the case of veratraldehyde where the carbonyl group was blocked. The high conversion could be explained by diffusion effects of intermediates and electronic effects between the reactants in the transition state. The catalyst was found to be active after three cycles.

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The Synthesis of α-Amino-o-tolualdehyde Diethylacetal and its Attempted Conversion to Pseudoisoindole

Cited by 49 publications

References 0 publications

The use of anhydrous CeCl3 as a recyclable and selective catalyst for the acetalization of aldehydes and ketones

The use of anhydrous CeCl3 as a recyclable and selective catalyst for the acetalization of aldehydes and ketones

Synthesis of dimethyl acetal of ketones: design of solid acid catalysts for one-pot acetalization reaction

Acetalation of Pentaerithritol Catalyzed by an Al-Pillared Saponite

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