Terminal Alkyne-Assisted One-Pot Synthesis of Arylamidines: Carbon Source of the Amidine Group from Oxime Chlorides

A terminal alkyne-assisted protocol for the one-pot formation of a diverse range of arylamidines from a novel cascade reaction of in situ generated nitrile oxides, sulfonyl azides, terminal alkynes, and water by [3 + 2] cycloaddition and ring opening sequence was developed. The use of aryl oxime chl...

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Published inJournal of organic chemistry Vol. 84; no. 11; pp. 6780 - 6787
Main Authors Yi, Fengping, Sun, Qihui, Sun, Jing, Fu, Chao, Yi, Weiyin
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 07.06.2019
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
TRANSFORMATION
CYCLOADDITION
INSERTION
DIELS-ALDER REACTIONS
SULFONYL AZIDES
FACILE ACCESS
PALLADIUM-CATALYZED SYNTHESIS
NITRILE OXIDE
REACTIVITY
INHIBITORS
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Summary:A terminal alkyne-assisted protocol for the one-pot formation of a diverse range of arylamidines from a novel cascade reaction of in situ generated nitrile oxides, sulfonyl azides, terminal alkynes, and water by [3 + 2] cycloaddition and ring opening sequence was developed. The use of aryl oxime chlorides as the carbon source of the amidine group and the addition of water proved to be critical for the reaction. Moreover, terminal alkynes, which can lead to high yields of products by employing a less amount, may play a catalytic role in the reaction. A broader range of substrates was investigated.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.9b00538