- Synthesis of Vinyl Isocyanides and Development of a Convertible Isonitrile
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The reaction of isocyanomethylenetriphenylphosphorane, generated in situ from the corresponding phosphonium salt, with a diverse set of aldehydes afforded vinyl isocyanides in good to high yields. Excellent E-selectivity was observed for aliphatic aldehydes and 2,6-disubstituted aromatic aldehydes, whereas Z-olefins were formed predominantly with ortho-substituted aryl aldehydes. (Z)-1-Bromo-2-(2-isocyanovinyl)benzene (5l) was found to be a truly universal isonitrile since, after Ugi reaction, the resulting secondary amide unit (RNHCO-) is convertible under both acidic and basic conditions. The application of 5l in the synthesis of polyheterocycles is also illustrated.
- Spallarossa, Martina,Wang, Qian,Riva, Renata,Zhu, Jieping
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supporting information
p. 1622 - 1625
(2016/05/02)
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- Process for the synthesis of imidazoles
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The present invention provides a process for the preparation of imidazoles by reacting a cyano compound with a silylalkylisocyanide compound. Such imidazoles are useful pharmacologically-active compounds and/or intermediates for the preparation of pharmacologically-active compounds.
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Page/Page column 5
(2008/06/13)
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- AN IMPROVED SYNTHESIS OF TRIMETHYLSILYLMETHYL ISOCYANIDE
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Trimethylsilylmethyl isocyanide is prepared by a new method which gives a higher overall yield and circumvents the use of methyl isocyanide.
- Brouwer, Antoon C.,Leusen, Albert M. van
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p. 865 - 870
(2007/10/02)
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- Alkaloid synthesis via the intramolecular imidate methylide 1,3-dipolar cycloaddition reaction
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A concise synthesis for the neurotoxic physostigmine alkaloid d,l-eserethole is described which relys upon an intramolecular cycloaddition reaction involving a "non-stabilized" imidate methylide and an unactivated alkene. The facility of this cyclization
- Smith, Richard,Livinghouse, Tom
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p. 3559 - 3568
(2007/10/02)
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- The Direct Generation of N-Acyl Formimidate Methylides. An Efficient Approach to the Synthesis of Pyrrolidine Derivatives
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The reaction of silyl-formamidines and silyl-thioformimidates with acyl fluorides gives N-acyl imidate methylides which have been successfully trapped with several dipolarophiles to afford pyrrolidine derivatives in high yields.
- Livinghouse, Tom,Smith, Richard
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p. 210 - 211
(2007/10/02)
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