Electric Literature of C7H7NOIn 2021 ,《Divergent, Strain-Release Reactions of Azabicyclo[1.1.0]butyl Carbinols: Semipinacol or Spiroepoxy Azetidine Formation》 was published in Angewandte Chemie, International Edition. The article was written by Gregson, Charlotte H. U.; Noble, Adam; Aggarwal, Varinder K.. The article contains the following contents:
The azetidine moiety is a privileged motif in medicinal chem. and new methods that access them efficiently are highly sought after. Towards this goal, we have found that azabicyclo[1.1.0]butyl carbinols, readily obtained from the highly strained azabicyclo[1.1.0]butane (ABB), can undergo divergent strain-release reactions upon N-activation. Treatment with trifluoroacetic anhydride or triflic anhydride triggered a semipinacol rearrangement to give keto 1,3,3-substituted azetidines. More than 20 examples were explored, enabling us to evaluate selectivity and the migratory aptitude of different groups. Alternatively, treatment of the same alcs. with benzyl chloroformate in the presence of NaI led to iodohydrin intermediates which gave spiroepoxy azetidines upon treatment with base. The electronic nature of the activating agent dictates which pathway operates. In addition to this study using 4-Acetylpyridine, there are many other studies that have used 4-Acetylpyridine(cas: 1122-54-9Electric Literature of C7H7NO) was used in this study.
4-Acetylpyridine(cas: 1122-54-9) belongs to pyridine. Pyridine and pyridine-derived structures are privileged pharmacophores in medicinal chemistry and an essential functionality for organic chemists. As the prototypical π-deficient heterocycle, pyridine illustrates distinctive chemistry as both substrate and reagent. Electric Literature of C7H7NO