N-Allyl-N-sulfonyl Ynamides as Synthetic Precursors to Amidines and Vinylogous Amidines. An Unexpected N-to-C 1,3-Sulfonyl Shift in Nitrile Synthesis
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چکیده
منابع مشابه
Synthesis of N-Sulfonyl Amidines and Acyl Sulfonyl Ureas from Sulfonyl Azides, Carbon Monoxide, and Amides.
A Pd-catalyzed and ligand-free carbonylation/cycloaddition/decarboxylation cascade synthesis of sulfonyl amidines from sulfonyl azides and substituted amides at low CO pressure is reported. The reaction proceeds via an initial Pd-catalyzed carbonylative generation of sulfonyl isocyanates from sulfonyl azides, followed by a [2 + 2] cycloaddition with amides and subsequent decarboxylation, which ...
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Cu-catalyzed aerobic oxidative three-component coupling of a terminal alkyne, secondary amine, and sulfonamide enables efficient synthesis of amidines. The use of Cu(OTf)2 (5 mol %) produces amidines selectively without Glaser-Hay alkyne homocoupling products. Preliminary studies suggest that the reaction pathway involves initial oxidative coupling of the terminal alkyne with the secondary amin...
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The scope and limitations of a photoinitiated N- to C-sulfonyl migration process within a range of dihydropyridinones is assessed. This sulfonyl transfer proceeds without erosion of either diastereo- or enantiocontrol, and is general across a range of N-sulfonyl substituents (SO2R; R = Ph, 4-MeC6H4, 4-MeOC6H4, 4-NO2C6H4, Me, Et) as well as C(3)-(aryl, heteroaryl, alkyl and alkenyl) and C(4)-(ar...
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An immense effort has been made to develop efficient strategies for the direct functionalization of C H bonds using transition-metal catalysis. For the most part, ruthenium-, rhodium-, and palladium-based catalysts have been applied to effect either C C or C Het (Het= heteroatom) bond formation by replacement of a C H bond. Few examples have been described that employ copper as catalysts, which...
متن کاملBase-catalyzed cyclization of N-sulfonyl propargylamides to sulfonylmethyl-substituted oxazoles via sulfonyl migration.
The reaction of N-sulfonyl propargylamides in the presence of a base catalyst selectively affords 5-sulfonylmethyl oxazoles via 1,4-sulfonyl migration. Allenes have been established as the key intermediates. Experimental evidence has been provided to support a two-step mechanism in the cyclization.
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ژورنال
عنوان ژورنال: The Journal of Organic Chemistry
سال: 2011
ISSN: 0022-3263,1520-6904
DOI: 10.1021/jo200780x