Chemistry of Heterocyclic Compounds: Oxazoles, Volume 45 by I. J. Turchi
By I. J. Turchi
A reference that describes the entire very important syntheses and reactions of oxazoles and oxazolones released during the first region of l984. Emphasizes using oxazoles as man made reagents in addition to proposing the extra classical remedies of oxazole chemistry. comprises the single wide record of tables of oxazole derivatives and the main entire record of spectroscopic homes of oxazoles. bargains the main particular remedy of mesoionic oxazoles together with syntheses, specroscopy and reactions.Content:
Chapter 1 Oxazoles (pages 1–341): Ignatius J. Turchi
Chapter 2 Spectroscopic houses of Oxazoles (pages 343–360): Cynthia A. Maryanoff
Chapter three Oxazolones (pages 361–729): Y. Shyamsunder Rao and Robert Filler
Chapter four Mesoionic Oxazoles (pages 731–961): Henry L. Gingrich and Jonathan S. Baum
Chapter five Oxazoles and Oxazolines in natural Synthesis (pages 963–1017): Bruce E. Maryanoff
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Extra info for Chemistry of Heterocyclic Compounds: Oxazoles, Volume 45
The reaction of 2-phenyl-4-methyloxazole (169) with bromine is of interest. I IBr Synthesis and Reactions of Functionalized Oxazoles 41 90% yield along with the hydrobromide salt of 169. Addition of a second equivalent of bromine yields a perbromide and an N-bromo derivative whose structures are represented b y 171 and 172, respectively. '43 Further examples of this process are 1 6 9 . H B r + 170 Br2 171 Ph I )$ Br 173 172 R' R' R' R' R' R' R' Br = Me; RZ = Ph (60%)'43 = H, Me; RZ = Ph (85%)'O0 = H , M e , P h ; RZ = XPhI3' = 4-AcNHPh; R2 = M e (85%)'48 = XPh; R2 = CH2C1'49 5-Acetoxymercurioxazoles are easily transformed into the corresponding 5bromo- or 5-iodooxazoles in good yields with bromine or iodine as is the case for the 2- and 4-acetoxymercurioxazoles 151 and 159, r e ~ p e c t i v e l y , ' ~ ' ~ ' ~ ~ The reduction of 5-halooxazoles with hydrogen/palladium on charcoal or zinc in acetic acid leads t o 5-unsubstituted oxazoles.
23) The reaction of phenyloxazoles with electrophiles in general leads to the formation of substituted phenyloxazoles because of the low reactivity of the oxazole nucleus toward these species. Substitution occurs in the 4-position of the phenyl moiety with the order of reactivity being dependent on the position it occupies on the oxazole ring, that is, 5-Ph > 4-Ph & 2-Ph. The phenyl substituents thus introduced 29 Synthesis and Reactions of Alkyl-, Aryl-, and Aralkyloxazoles undergo the normal types of reactions expected of these functional groups.
13's132 152 151 Because of the reactivity of 2-chlorooxazoles toward nucleophilic displacement reactions, these derivatives are useful intermediates in the preparation of 2-aminooxazoles 153 Similarly the 2-alkoxyoxazoles 154, X = 0,128,'34~135 2can be obtained alkylthiooxazoles 154, X = S,13' and 2-hydrazinoo~azoles'~~ usually in good yields. 1283130,133 / R' 153 R' , R2 = alkyl, aryl; R3,R4 = H, alkyl a w ~ 1 2 8 . 55 P h q o $ Ph CN 156 4-Halooxazoles are available by several methods. " Ignatius J.