Oxazolines reaction with, phosgene

The preparation of 3,5-diphenyl-4-oxazolin-2-one by reaction of phenacylaniline with phosgene was described by McCombie and Scarborough, who also showed that the 3,4,5-triphenyl analog was an extremely stable compound which failed to react with a variety of... 

Conversion of 2 to the highly crystalline oxazolidinone 3 with phosgene has been described by Thornton who has employed this substance as a chiral auxiliary in asymmetric aldol reactions of its N-propionyl derivative. Kelly has also used an oxazoline derived from 3 as a chiral auxiliary in asymmetric alkylation of a glycolate enolate. Oxazolidinone 3 has also been prepared from 2 with diethyl carbonate in the presence of potassium carbonate. The conversion of 2 to the oxazolidinone 3 is accomplished using triphosgene in this procedure because of the high toxicity of phosgene. 

The reaction of phosgene [75-44-5] or thiophosgene [463-71-8] with ethyleneimine yields either a bisaziridine compound (l,l -carhonylhisaziridine [1192-75-2] on l,T-thiocarbonylhisaziridine [13163-23-0]) or a 2-chloroethyliso(thio)cyanate, depending on the reaction conditions. The former can he isomerized by catalysis with triiodide to give l-aziridinyl-2-oxazoline [19587-77-0] or l-aziridinyl-2-thiazoline [17205 18-0] (173—177). 

Highlights of iome reactions of phosgene with amines, imines. oxazolines... 

Finally, in an intriguing reaction, phosgene reacts with 2-aziridinyl-2-oxazoline to form the trimer of 2-chloroethyl isocyanate [2042a] ... 

The action of phosgene or thionyl chloride on the )V-(benzyl-oxycarbonyl)amino-acids PhCH202CNHCHRC02H (R == PhCH2 or Pr ) yields 2-oxazolin-5-ones (522), contrary to a previous report/ Numerous 3-oxazolin-5-ones (523 R , R R = alkyl or Ph) have been prepared from hydroxylamino-acids H0NHCHR C02H and ketones R COR. The revised structure (524) has been established by X-ray diffraction for the product of the reaction of ethyl diazoacetate with di-isopropylcarbodi-imide, catalysed by salts of transition metals. Treatment of the diazomethylphosphoryl compound (Me0)2P(0)CHN2 with aroyl isocyanates affords the 2-oxazolin-4-ones (525)/ ... 

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