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Novel 2,5‐Disubstituted 1,3‐Dioxanes and Oxazolidines as Potential Chemoprevention Agents and Building Blocks for Organic Synthesis
Author(s) -
Rüger Anne J.,
Nieger Martin,
EsSayed Mazen,
Bräse Stefan
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201000339
Subject(s) - chemistry , hydroxymethyl , combinatorial chemistry , diol , organic synthesis , stereochemistry , organic chemistry , catalysis
2,5‐Disubstituted 1,3‐dioxacycloalkanes have recently been found to be promising lead compounds that possess potent anti‐inflammatory activity and therefore may act as chemoprevention agents. Encouraged by this we have designed and synthesized a new series of 5‐amino‐2‐heteroaryl‐1,3‐dioxanes. Starting from N ‐protected 2‐aminopropane‐1,3‐diol and the corresponding aromatic aldehydes, the products were isolated without isomeric inversion at the deprotection step. This is the first broadly applicable synthetic approach to the acetalization of heteroaromatic aldehydes to give 5‐amino‐1,3‐dioxanes. Our route provides a mild access to both isomers of this kind of dioxane, that is, cis and trans products, as well as 4‐(hydroxymethyl)‐2‐heteroaryloxazolidines, which are useful building blocks in organic synthesis.