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 Traceless Electrophilic Amination for the Synthesis of Unprotected Cyclic β-Amino Acids, published in 2019-07-03, which mentions a compound: 114527-53-6, mainly applied to cyclic beta amino acid preparation electrophilic amination, Name: 1,2,3,4-Tetrahydroquinoline-3-carboxylic acid.
Electrophilic aminations involve an umpolung of a nitrogen atom, providing an alternate, distinctive synthetic strategy. The recent advent of various designed O-substituted hydroxylamines has significantly advanced this research field. An underappreciated issue is atom economy of the transformations: The necessary activating group on the oxygen atom is left in coproduced waste. Herein, the authors describe Rh-catalyzed electrophilic amination of substituted isoxazolidin-5-ones for the synthesis of unprotected, cyclic β-amino acids featuring either benzo-fused or spirocyclic scaffolds. Using the cyclic hydroxylamines allows for retaining both nitrogen and oxygen functionalities in the product. The traceless, redox neutral process proceeds on a gram scale with as little as 0.1 mol % catalyst loading. In contrast to related electrophilic aminations in the literature, a series of mechanistic experiments suggests a unique pathway involving spirocyclization, followed by the skeletal rearrangement. The insights provided herein shed light on a nuanced reactivity of the active species, Rh-nitrenoid generated from the activated hydroxylamine, and extend the knowledge on electrophilic aromatic substitutions.
Compound(114527-53-6)Name: 1,2,3,4-Tetrahydroquinoline-3-carboxylic acid received a lot of attention, and I have introduced some compounds in other articles, similar to this compound(1,2,3,4-Tetrahydroquinoline-3-carboxylic acid), if you are interested, you can check out my other related articles.
Reference:
Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com