Use of ethyl (benzothiazol-2-ylsulfonyl)acetate for malonic ester-type syntheses of carboxylic acids and esters

Waleed M. Hussein; Ross P. McGeary

doi:10.1071/CH14085

Use of ethyl (benzothiazol-2-ylsulfonyl)acetate for malonic ester-type syntheses of carboxylic acids and esters

Waleed M. Hussein, Ross P. McGeary

Research output: Contribution to journal › Article › Research › peer-review

1 Citation (Scopus)

Abstract

A new methodology for the synthesis of substituted carboxylic acids is described. Alkylation of either ethyl (benzothiazol-2-ylsulfonyl)acetate or ethyl 2-(benzothiazol-2-ylsulfonyl)propionate was achieved with alkyl halides and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) in dichloromethane solution. These products were then desulfinated and hydrolysed in one-pot under mild conditions to give substituted acetic acids in good-to-excellent yields.

Original language	English
Pages (from-to)	1222-1227
Number of pages	6
Journal	Australian Journal of Chemistry
Volume	67
Issue number	9
DOIs	https://doi.org/10.1071/CH14085
Publication status	Published - 12 May 2014
Externally published	Yes

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abstract = "A new methodology for the synthesis of substituted carboxylic acids is described. Alkylation of either ethyl (benzothiazol-2-ylsulfonyl)acetate or ethyl 2-(benzothiazol-2-ylsulfonyl)propionate was achieved with alkyl halides and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) in dichloromethane solution. These products were then desulfinated and hydrolysed in one-pot under mild conditions to give substituted acetic acids in good-to-excellent yields.",

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AU - McGeary, Ross P.

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Y1 - 2014/5/12

N2 - A new methodology for the synthesis of substituted carboxylic acids is described. Alkylation of either ethyl (benzothiazol-2-ylsulfonyl)acetate or ethyl 2-(benzothiazol-2-ylsulfonyl)propionate was achieved with alkyl halides and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) in dichloromethane solution. These products were then desulfinated and hydrolysed in one-pot under mild conditions to give substituted acetic acids in good-to-excellent yields.

AB - A new methodology for the synthesis of substituted carboxylic acids is described. Alkylation of either ethyl (benzothiazol-2-ylsulfonyl)acetate or ethyl 2-(benzothiazol-2-ylsulfonyl)propionate was achieved with alkyl halides and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) in dichloromethane solution. These products were then desulfinated and hydrolysed in one-pot under mild conditions to give substituted acetic acids in good-to-excellent yields.

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DO - 10.1071/CH14085

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JO - Australian Journal of Chemistry

JF - Australian Journal of Chemistry

IS - 9

ER -

Use of ethyl (benzothiazol-2-ylsulfonyl)acetate for malonic ester-type syntheses of carboxylic acids and esters

Abstract

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