Conformationally Flexible C 3-Symmetric 1,3-Oxazoles as Molecular Scaffolds

Abstract

Flexible-arm, C 3 -symmetric tris-oxazoles are synthesized for their applications in supramolecular chemistry and materials science. The C 3 -symmetry is introduced starting from 1,3,5-trimethylbenzene and carrying out threefold reactions at each stage of the synthesis. The applicability of these tris-oxazoles is demonstrated by transforming a representative example into a highly fluorescent material. This is accomplished by conjugation with an aromatic moiety via palladium(0)catalyzed direct arylation at C-2 of the oxazole. A unique molecular arrangement in the crystal structure is observed.

Modular Approach to Benzofurans, 2H‐Chromenes and Benzoxepines via Claisen Rearrangement and Ring‐Closing Metathesis: Access to Phenylpropanoids

“…For this purpose, Van Leusen oxazole synthesis [37c,d, e] was employed. The aldehyde derivatives 29 a, 32 a and 34 a were treated with p ‐toluenesulfonylmethyl isocyanide (TosMIC)/(K 2 CO 3 ) in methanol (MeOH) under reflux conditions to deliver the benzofuran 36 and 2 H ‐chromenes 37 containing oxazole moiety in 97% and 98% yields, respectively.…”

Heteroditopic Macrobicyclic Molecular Vessels for Single Step Aerial Oxidative Transformation of Primary Alcohol Appended Cross Azobenzenes

“…All the starting materials were purchased from commercial sources such as Sigma-Aldrich, Merck, Spectrochem, and Alfa Aesar and are used as received without further purification. Compounds 1 , 2a , 2b , and M1 were prepared by following previously reported procedures. Primary alcohol based aromatic amine substrates 6 and 7 were synthesized in high yields using the generalized reduction procedure from corresponding carboxylic acids .…”

An overview of the synthetic strategies ofC3-symmetric polymeric materials containing benzene and triazine cores and their biomedical applications

“…The designed trialdhyde was formed in two ways, tribromo with nBuLi and N-formylpiperidine or formylation of tristhiophene derivative by Vilsmeier-Haack reaction using POCl 3 in DMF (Table 2, entry 1). 53,54…”