In organic chemistry, atoms other than carbon and hydrogen are generally referred to as heteroatoms. The most common heteroatoms are nitrogen, oxygen and sulfur. Now I present to you an article called Divergent, Strain-Release Reactions of Azabicyclo[1.1.0]butyl Carbinols: Semipinacol or Spiroepoxy Azetidine Formation, published in 2021-03-29, which mentions a compound: 23794-15-2, mainly applied to semipinacol azetidine preparation strain release rearrangement azabicyclo Bu carbinol; spiroepoxy azetidine divergent preparation strain release nucleophilic ring expansion; azabicyclo[1.1.0]butane; azetidines; epoxides; ring expansion; strained molecules, Application In Synthesis of 1-(2-chloropyridine-4-yl)ethanone.
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.
《Divergent, Strain-Release Reactions of Azabicyclo[1.1.0]butyl Carbinols: Semipinacol or Spiroepoxy Azetidine Formation》 provides a strategy for the preparation of materials with excellent comprehensive properties, which is conducive to broaden the application field of this compound(1-(2-chloropyridine-4-yl)ethanone)Application In Synthesis of 1-(2-chloropyridine-4-yl)ethanone.
Reference:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem