Formation of Heterocyclic and Polycyclic Compounds from Amino Alcohols and Dialdehydes

Abstract

Amino alcohols typically react with aldehydes to produce oxazolidines. It was hypothesized that the condensation of several commercially available amino alcohols with dialdehydes would produce a series of bicyclic oxazolidines containing two secondary amines. However, there were remarkable differences in the type of products formed depending on the structure of the dicarbonyl compounds and the reaction conditions. When linear aliphatic dialdehydes such as glyoxal were used, the expected bis‐oxazolidines were not produced; instead, polycyclic structures or oxazines were formed. However, when cyclic dialdehydes such as 1,3/1,4 cyclohexane dicarboxaldehyde were used, they resulted in products bearing the desired oxazolidine moieties.

Stereoselective synthesis and application of bi- and trifunctional monoterpene-based compounds

“…Fu and Chen reported the synthesis of diaminoalcohols via stereoselective Ugi-reaction starting from α,α'-iminodiacetic acid analogues 109. Reaction of nitroalkanes with α,β-unsaturated aldehydes and subsequent catalytic hydrogenation can also lead to the aforementioned moiety 110. Rondotet al reported the efficient regio-and stereoselective synthesis of diaminoalcohol derived dihydrooxazines (CXIX) from readily accessible aminodiol CXVIII via trichloroacetimidate intermediates.…”