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使用催化烯醇化物芳基化和原位官能化进行模块化异喹啉合成。

Modular isoquinoline synthesis using catalytic enolate arylation and in situ functionalization.

机构信息

Department of Chemistry, University of Oxford , Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, U.K., and GlaxoSmithKline , Medicines Research Centre, Gunnels Wood Road, Stevenage, SG1 2NY, U.K.

出版信息

Org Lett. 2013 Dec 20;15(24):6190-3. doi: 10.1021/ol4030309. Epub 2013 Nov 19.

DOI:10.1021/ol4030309
PMID:24251885
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3880054/
Abstract

A methyl ketone, an aryl bromide, an electrophile, and ammonium chloride were combined in a four-component, three-step, and one-pot coupling procedure to furnish substituted isoquinolines in overall yields of up to 80%. This protocol utilizes the palladium catalyzed α-arylation reaction of an enolate, followed by in situ trapping with an electrophile, and aromatization with ammonium chloride. tert-Butyl cyanoacetate participated in a similar protocol; after functionalization and decarboxylation, 3-amino-4-alkyl isoquinolines were prepared in high yield.

摘要

将甲基酮、芳基溴化物、亲电试剂和氯化铵在四组分、三步和一锅耦联程序中组合在一起，以高达 80%的总收率提供取代的异喹啉。该方案利用钯催化的烯醇化物的α-芳基化反应，然后用亲电试剂原位捕获，并用氯化铵进行芳构化。叔丁基氰基乙酸酯参与了类似的方案; 经过官能化和脱羧后，以高产率制备 3-氨基-4-烷基异喹啉。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/333e/3880054/ab9592303b1e/ol-2013-030309_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/333e/3880054/d85cf62c4483/ol-2013-030309_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/333e/3880054/5326335fd79f/ol-2013-030309_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/333e/3880054/ae867ecde872/ol-2013-030309_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/333e/3880054/875096812016/ol-2013-030309_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/333e/3880054/0e0782572b08/ol-2013-030309_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/333e/3880054/ab9592303b1e/ol-2013-030309_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/333e/3880054/d85cf62c4483/ol-2013-030309_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/333e/3880054/5326335fd79f/ol-2013-030309_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/333e/3880054/ae867ecde872/ol-2013-030309_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/333e/3880054/875096812016/ol-2013-030309_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/333e/3880054/0e0782572b08/ol-2013-030309_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/333e/3880054/ab9592303b1e/ol-2013-030309_0007.jpg

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