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Application of the heck reaction for the synthesis of 1-alkoxyisoquinoline- 3-carboxylic acids esters

Identifieur interne : 000653 ( Main/Exploration ); précédent : 000652; suivant : 000654

Application of the heck reaction for the synthesis of 1-alkoxyisoquinoline- 3-carboxylic acids esters

Auteurs : A. Ture [Lettonie] ; K. Rubina [Lettonie] ; E. Rozhkov [Lettonie] ; V. Kauss [Lettonie]

Source :

RBID : ISTEX:BCC26459804A6A191B94FD0BCF1BF37473ECF675

English descriptors

Abstract

It has been shown that the cyclization of the methyl 2-(2,2,2-trifluoroacetylamino)acrylate arylation product using methyl 4,6-dichloro-2-iodobenzoate gives the corresponding 1-methoxyisoquinoline-3-carboxylic acid ester through loss of water rather than methanol. This feature of the condensation has been used for the synthesis of methyl 1-(tert-butoxycarbonylmethoxy)isoquinoline-3-carboxylate.

Url:
DOI: 10.1007/s10593-011-0844-7


Affiliations:


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<term>Sodium chloride solution</term>
<term>Sodium sulfate</term>
<term>Suzuki reaction</term>
<term>Tetrabutylammonium bromide</term>
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<div type="abstract" xml:lang="en">It has been shown that the cyclization of the methyl 2-(2,2,2-trifluoroacetylamino)acrylate arylation product using methyl 4,6-dichloro-2-iodobenzoate gives the corresponding 1-methoxyisoquinoline-3-carboxylic acid ester through loss of water rather than methanol. This feature of the condensation has been used for the synthesis of methyl 1-(tert-butoxycarbonylmethoxy)isoquinoline-3-carboxylate.</div>
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