2006/10/12 by Mohammad Movassaghi, Matthew D. Hill · 2 citations
Chemistry · #Advanced Synthetic Organic Chemistry #Chemical synthesis and alkaloids #Quinazolinone synthesis and applications
paper · doi:10.1021/ja066405m
openalex publication_date 2006/10/12 · openalex created_date 2025/10/10 · openalex updated_date 2026/07/28
We describe a single-step conversion of various N-vinyl and N-aryl amides to the corresponding pyrimidine and quinazoline derivatives, respectively. The process involves amide activation with 2-chloropyridine and trifluoromethanesulfonic anhydride followed by nitrile addition into the reactive intermediate and cycloisomerization. In situ nitrile generation from primary amides allows for their use as nitrile surrogates. The use of this chemistry with sensitive N-vinyl amides and epimerizable substrates in addition to a wide range of functional groups is noteworthy.