By I. J. Turchi
A reference that describes all the vital syntheses and reactions of oxazoles and oxazolones released in the course of the first area of l984. Emphasizes using oxazoles as man made reagents in addition to featuring the extra classical remedies of oxazole chemistry. comprises the single broad record of tables of oxazole derivatives and the main whole checklist of spectroscopic homes of oxazoles. bargains the main specified therapy 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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Additional resources for Chemistry of Heterocyclic Compounds: Oxazoles, Volume 45
Example text
O0 Deprotonation of ethyl 4-me thyloxazole-5-carboxylate (258) with lithium isopropylcyclohexyl amide followed by reaction of the anion with a halogenating agent affords 259 in modest yields. Ethyl 2-chloro-4-trifluoromethyloxazole-5-carboxylate (261) was prepared 1. LICA COzEt 2. '" These compounds are effective in reducing injury to plants caused by certain herbicides. ''l The proethyl 2-chloro-5-ethoxyoxazole-4-carboxylate posed mechanism for this transformation involves attack of dichlorocarbene (generated by the thermolysis of phenyl trichloromethylmercury) on the imine nitrogen leading to the azomethine ylide 264, which undergoes a 1,5-dipolar cyclization to give the 4-oxazoline 265.
The thermal decompoin the presence of aryl anhydrides in 2sition of 2,4-diphenyl-2-oxazolin-5-one picoline leading to 2,4-diphenyl-5-aryloxazoleswas first described by L a w ~ o n . ' ~ This reaction probably proceeds via the 4-aroyl-2-oxazolin-5-ones. Hofle and Synthesis and Reactions of Alkyl-, Aryl-, and Aralkyloxazoles 23 Steglich reported the results of a study of the scope and mechanism of this unusual and preparatively useful i n t e r c o n v e r ~ i o n . When ~~ 4-acyl-2- and 2-acyl-3-oxalin5-ones 105 and 106 respectively, are heated, oxazoles are formed in good yields.
Ignatius J. 10) produced as outlined above. /(:W 7 NHCOR + 4-02NPhCHO 137 A PY 1 --co, 139 R = H, Me, Ph; Ar = 4-0,NPh The 1,3-dipolar cycloaddition of carbonyl ylides to various dipolarophiles provides oxygen-containing h e t e r o ~ y c 1 e s . l ~Consequently ~ these dipolar species have the potential to act as intermediates leading to oxazoles or oxazolines if allowed to combine with nitriles. 0] pentane 140 is trapped by aryl nitriles to afford the nonisolable bicyclic intermediate 142. lZ6 + ph&ph 120° 140 - [ P h e P h ] 141 142 Ar = Ph, 4-MePh Synthesis and Reactions of Alkyl-, Aryl-, and Aralkyloxazoles 35 Another type of 1,3-dipole, the N-benzoylamino carbene 145 is the proposed intermediate in the pyrolytic decomposition of l-benzoyl-4,S-diphenyl-l,2,3triazole (144).