Synthesis of α-Quaternized 2,4-Cyclohexadienones from Propargyl Vinyl Ethers
نویسندگان
چکیده
منابع مشابه
Coupled domino processes: synthesis of 3,5,8-trisubstituted coumarins from propargyl vinyl ethers.
The generation of a small and representative library of 3,5,8-trisubstituted coumarins (21 compounds, 7 families, 3 groups) is described. The library was built from the corresponding propargyl vinyl ethers and three different 1,3-dicarbonyl derivatives using a one-pot coupled domino strategy. These coumarins constitute a novel chemotype defined by the presence of a chemical handle in the pyrano...
متن کاملPropargyl Vinyl Ethers and Tertiary Skipped Diynes: Two Pluripotent Molecular Platforms for Diversity-Oriented Synthesis.
During the last years, we have been involved in the development of a diversity-oriented synthetic strategy aimed at transforming simple, linear, and densely functionalized molecular platforms into collections of topologically diverse scaffolds incorporating biologically relevant structural motifs such as N- and O- heterocycles, multifunctionalized aromatic rings, fused macrocycles, etc. The str...
متن کاملMicrowave-assisted domino access to C2-chain functionalized furans from tertiary propargyl vinyl ethers.
Tertiary propargyl vinyl ethers armed with an electron-withdrawing group (amide or ester) at the tertiary propargylic position have been efficiently transformed into trisubstituted C(2)-chain functionalized furans. The metal-free domino transformation involves a microwave-assisted tandem [3,3]-propargyl Claisen rearrangement/5-exo-dig O-cyclization reaction. The manifold can be performed in a o...
متن کاملSynthesis of Functionalized Aryl-vinyl Ethers as Building Blocks and Auxiliaries in Organic Synthesis
5- hydroxyisoquinoline undergoes a smooth reaction with alkyl propiolates in the presence of triphenylphosphine (15 mol%) to produce the corresponding (E)-alkyl 3-(isoquinolin-5-yloxy) acrylate in good yields. When the reaction was performed by 2-methyl 4-hydroxyquinoline and 3-nitro 4-hydroxypyridine, similar aryl vinyl ethers were obtained.
متن کاملTriphenylphosphine mediated synthesis of functionalized aryl-vinyl ethers from7-hydroxy coumarin and methyl acetylene carboxylate
7-hydroxy coumarin undergoes neutral conditions with alkyl propiolates in the presence of triphenylphosphine, and bysubstituation the corresponding aryl vinyl ethers was obtained in good yields
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ژورنال
عنوان ژورنال: The Journal of Organic Chemistry
سال: 2016
ISSN: 0022-3263,1520-6904
DOI: 10.1021/acs.joc.6b02137