Synthesis of New Sulfoximine‐Tethered Alkynones and Further Extension towards Metal‐Free Synthesis of Pyrimidines, Amino Pyrimidines, Pyrazoles and Isoxazoles
Abstract:A metal free and divergent synthetic method has been successfully developed for the synthesis of sulfoximine tethered pyrimidines, amino pyrimidines, pyrazoles and isoxazoles. Two key sulfoximine tethered alkynone intermediates ((tert‐butyldiphenylsilyl)imino)(2‐oxo‐4‐phenylbut‐3‐yn‐1‐yl)(phenyl)‐λ6‐sulfanone (3 a) and ((tert‐butyldiphenylsilyl)imino)(2‐oxopent‐3‐yn‐1‐yl)(phenyl)‐λ6‐sulfanone (3 b), have been reported for the first time and were used as the common building blocks to construct these heterocycle… Show more
“…Now, we have discovered highly selective cyclization reactions of S -methyl derivatives of N -ynonylsulfoximines providing three-dimensional heterocycles 2 under very mild reaction conditions (Scheme ). In this Letter, we summarize the initial observations and subsequent optimization studies.…”
Upon
treatment with Cs2CO3, S-methyl-N-ynonylsulfoximines undergo 5-exo-dig cyclizations
to give three-dimensional heterocycles. The reactions proceed at ambient
temperature with a wide range of substrates affording the corresponding
products in good to excellent yields.
“…Now, we have discovered highly selective cyclization reactions of S -methyl derivatives of N -ynonylsulfoximines providing three-dimensional heterocycles 2 under very mild reaction conditions (Scheme ). In this Letter, we summarize the initial observations and subsequent optimization studies.…”
Upon
treatment with Cs2CO3, S-methyl-N-ynonylsulfoximines undergo 5-exo-dig cyclizations
to give three-dimensional heterocycles. The reactions proceed at ambient
temperature with a wide range of substrates affording the corresponding
products in good to excellent yields.
A divergent approach with a wide substrate scope has been successfully developed for the synthesis of N-1,2,4-oxadiazole tethered sulfoximines starting from N-cyano sulfoximines.
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