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Oxazolidine is a five-membered heterocycle ringwith the formula (CH 2) 3 (NH)O.The O atom and NH groups are not mutually bonded, in contrast to isoxazolidine. [ 2 ] [ 3 ] Oxazolidines (emphasis on plural) are derivatives of the parent oxazolidine owing to the presence of substituents on carbon and/or nitrogen.
The synthesis of 2-oxazoline rings is well established and in general proceeds via the cyclisation of a 2-amino alcohol (typically obtained by the reduction of an amino acid) with a suitable functional group. [5] [6] [7] The overall mechanism is usually subject to Baldwin's rules.
Oxazolidinones are useful as Evans auxiliaries, which are of interest for chiral synthesis. In a common implementation, an acid chloride substrate reacts with a chiral oxazolidinone to form an imide. Substituents at the 4 and 5 position of the oxazolidinone direct any aldol reaction to the alpha position of the carbonyl of the substrate. [6]
2-Oxazolidinone is the parent compound of several protein synthesis inhibitor antibiotics and the Evans chiral auxiliaries for aldol reactions. Cycloserine is an antibiotic based on the 3-isoxazolidone parent.
The routine use of pseudoproline (oxazolidine) dipeptides in the FMOC solid phase peptide synthesis (SPPS) of serine- and threonine-containing peptides leads to remarkable improvements in quality and yield of crude products and helps avoid unnecessary repeat synthesis of failed sequences. [14]
Synthesis of benzodiazepinones from azomethine ylide cyclizations. Cyclization of an azomethine ylide with a carbonyl affords a spirocyclic oxazolidine, which loses CO 2 to form a seven-membered ring. These high-utility decarboxylative multi-step reactions are common in azomethine ylide chemistry. [24]
Use of an oxazole in the synthesis of a precursor to pyridoxine, which is converted to vitamin B6. [6] In the Cornforth rearrangement of 4-acyloxazoles is a thermal rearrangement reaction with the organic acyl residue and the C5 substituent changing positions. Various oxidation reactions.
This was a remarkable result for the time and generated significant interest in the BOX motif. As the synthesis of 2-oxazoline rings was already well established at this time (literature reviews in 1949 [29] and 1971 [30]), research proceeded quickly, with papers from new groups being published within a year.