By David C. Palmer
Synthesis, Reactions, and Spectroscopy offers a finished assessment of the literature from 1983 to the current masking oxazoles, mesoionic oxazoles, oxazolones, oxazolines, and chiral bisoxazolines. In-depth insurance contains synthesis, reactions, spectroscopic and actual houses for every type of compounds, in addition to vital advancements concerning using these compounds.
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Additional info for The Chemistry of Heterocyclic Compounds, Oxazoles: Synthesis, Reactions, and Spectroscopy, Part B
Sample text
Proposed electrophilic attack on the 2-oxazolone moiety. 8. 42 R1 (exo) R2 (endo) ÀO OMe OBu OCH2CH2OMe OCH2OEt H Me a H H H H OMe H Temp ( C) À78 À78 À78 À78 À78 À78 À78 % Yield (% de) 58 (80) 89 (85) 85 (85) 79 (89) 79 (96) 36 (0) 80 (0) Data from Ref. 40. The (þ)- and (À)-4,5-dialkoxy-2-oxazolidinones 173 and 174 prepared through the 5-bromo-4-methoxy- derivatives serve as reliable chiral synthons for the preparation of a wide variety of optically active a-amino acids 176 and a-amino aldehydes 177 (Fig.
N-Phosphorylation The activated phosphorus reagents 269 and 270 are conventionally prepared by the reaction of 2(3H)-oxazolone with the corresponding phosphorus chlorides in the presence of triethylamine. The phosphorus chlorides employed include phosphoryl chloride, thiophosphoryl chloride, mono- and dichlorophosphates, and phosphinic chloride (Fig. 66). 82 The bis(2-oxo-3-oxazolinyl)phosphinate 282 is useful for Zr(IV)-catalyzed phosphorylation of alcohols, leading to the general synthesis of acid- and base-labile mixed phosphate esters 284 (Fig.
79 The 5-methyl-2(3H)-oxazolone sulfonamide derivatives 265 are obtained from the sulfonamides 263 via bromination and subsequent Stille coupling reaction with tetramethyltin in the presence of palladium catalyst (Fig. 61 Me ROC Me 1. AlCl 3 2. 6. 1. N-Acylation and N-Alkoxycarbonylation The parent 2(3H)-oxazolone moiety functions as a bifunctional leaving group when carboxyl groups are activated for acylations and condensations, similar to other five- and six-membered heterocycles such as imidazole, triazole, and 2-pyridinethiol.