A combinatorially convenient version of synthesis of 5-substituted oxazole-4-carboxylic acid ethyl esters

Article abstract of DOI:10.1134/S1070428006070177

Reaction of ethyl isocyanoacetic acid with sodium hydride in anhydrous benzene, followed by treatment with carboxylic acid chlorides or N-(acyloxy)pyrrolidine-2,5-diones, gives 5-substituted oxazole-4-carboxylic acid esters. The procedure is applicable to

Full text of DOI:10.1134/S1070428006070177

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ꢀꢋꢎꢃ+]ꢊꢅꢃꢏꢋꢇꢎꢃGꢋGꢃꢉꢀ+ꢅꢃ&+ꢅꢃ-ꢃ ꢃꢄꢋꢏꢅꢃꢀꢋꢎꢃ+]ꢊꢅꢃꢒꢋꢁꢒꢃGꢋGꢃ
ꢉꢀ+ꢅꢃ&+ꢅꢃ-ꢃ ꢃꢆꢋꢆꢅꢃꢁꢋꢏꢃ+]ꢊꢋꢃ &ꢃ105ꢃVSHFWUXPꢃ
ꢉ&'&O ꢊꢅꢃ ꢅꢃSSPꢓꢃꢀꢂꢋꢏꢌꢃꢉ&+ 8+ ꢊꢅꢃꢌꢀꢋꢂꢄꢃꢉ8+ &+ ꢊꢅꢃ
ꢀꢆꢆꢋꢏꢀꢃ ꢉ&+ꢊꢅꢃ ꢀꢆꢆꢋꢏꢆꢃ ꢉ&ꢊꢅꢃ ꢀꢆꢎꢋꢏꢆꢃ ꢉ& ꢊꢅꢃ ꢀꢂꢇꢋꢄꢏꢃ ꢉ&+ꢊꢅꢃ
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ꢀꢌꢀꢋꢆꢎꢃꢉ&2ꢊꢋꢃ)RXQGꢓꢃ0 ꢃꢆꢀꢏꢋꢁꢌꢏꢒꢋꢃ& + 1 2 ꢋꢃ&DOꢈ
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ꢇꢌKꢋꢃ/LJKWꢃ\HOORZꢃRLO\ꢃVXEVWDQFHꢋꢃ +ꢃ105ꢃVSHFWUXPꢃ
ꢉ&'&O ꢊꢅꢃ ꢅꢃSSPꢓꢃꢀꢋꢂꢄꢃWꢃꢉꢂ+ꢅꢃ&+ &C ꢅꢃ-ꢃ ꢃꢎꢋꢆꢃ+]ꢊꢅꢃ
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ꢎꢋꢎꢀꢃVꢃꢉꢀ+ꢅꢃ&+ꢊꢃꢉFIꢋꢃ>ꢀꢄ@ꢊꢋꢃ &ꢃ105ꢃVSHFWUXPꢃ
ꢉ&'&O ꢊꢅꢃ ꢅꢃ SSPꢓꢃ ꢀꢀꢋꢄꢎꢃ ꢉ&+ ꢊꢅꢃ ꢀꢂꢋꢒꢆꢃ ꢉ&+ 8+ ꢊꢅꢃ
ꢌꢁꢋꢇꢆꢃꢉ8+ &+ ꢊꢅꢃꢀꢆꢌꢋꢒꢏꢃꢉ& ꢊꢅꢃꢀꢄꢏꢋꢇꢁꢃꢉ& ꢊꢅꢃꢀꢇꢇꢋꢒꢏꢃ
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<LHOGꢃꢌꢌKꢋꢃ/LJKWꢃ\HOORZꢃRLO\ꢃVXEVWDQFHꢋꢃ +ꢃ105ꢃ
VSHFWUXPꢃꢉ&'&O ꢊꢅꢃ ꢅꢃSSPꢓꢃꢀꢋꢀꢁ±ꢀꢋꢌꢇꢃPꢃꢉꢌ+ꢅꢃꢂ&+ ꢊꢅꢃ
ꢀꢋꢂꢇꢃ Wꢃ ꢉꢂ+ꢅꢃ &+ &C ꢅꢃ-ꢃ ꢃꢎꢋꢆꢃ +]ꢊꢅꢃ ꢀꢋꢌꢇ±ꢀꢋꢒꢁꢃ Pꢃ ꢉꢄ+ꢅꢃ
ꢆ&+ ꢊꢅꢃꢂꢋꢄꢁꢃPꢃꢉꢀ+ꢅꢃ&+ꢊꢅꢃꢄꢋꢂꢀꢃTꢃꢉꢆ+ꢅꢃ&C &+ ꢅꢃ-ꢃ ꢃꢃ
ꢎꢋꢆꢃ+]ꢊꢅꢃꢎꢋꢌꢎꢃVꢃꢉꢀ+ꢅꢃ&+ꢊꢋꢃ &ꢃ105ꢃVSHFWUXPꢃꢉ&'&O ꢊꢅꢃ
ꢅꢃSSPꢓꢃꢀꢄꢋꢁꢇꢃꢉ&+ 8+ ꢊꢅꢃꢆꢇꢋꢄꢇꢃꢉ&+ ꢊꢅꢃꢆꢇꢋꢎꢇꢃꢉ&+ ꢊꢅꢃ
ꢂꢁꢋꢄꢀꢃꢉ&+ ꢊꢅꢃꢂꢇꢋꢂꢁꢃꢉ&+ꢊꢅꢃꢌꢁꢋꢌꢇꢃꢉ8+ &+ ꢊꢅꢃꢀꢆꢇꢋꢆꢎꢃ
ꢉ& ꢊꢅꢃꢀꢄꢏꢋꢂꢎꢃꢉ& ꢊꢅꢃꢀꢌꢀꢋꢒꢏꢃꢉ& ꢊꢅꢃꢀꢌꢂꢋꢌꢄꢃꢉ&2ꢊꢋꢃ)RXQGꢓꢃ
0 ꢃꢆꢆꢂꢋꢀꢆꢀꢇꢋꢃ& + 12 ꢋꢃ&DOFXODWHGꢓꢃ0ꢃꢆꢆꢂꢋꢀꢆꢁꢏꢋꢀ
@‡u’yꢀ $ꢂbꢅ(ꢆꢂ!ꢂꢅ!ꢂ‡uvr’yꢆr‡ur’yd‚‘h“‚yrꢂ#ꢂphꢁꢂ
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ꢁꢋꢏꢃ+]ꢊꢅꢃꢎꢋꢂꢏꢃꢉꢆ+ꢅꢃ$%ꢃV\VWHPꢅꢃ-ꢃ ꢃꢀꢌꢋꢁꢃ+]ꢊꢅꢃꢎꢋꢎꢄꢃVꢃ
ꢉꢀ+ꢅꢃ&+ꢊꢋꢃ &ꢃ105ꢃVSHFWUXPꢃꢉ&'&O ꢊꢅꢃ ꢅꢃSSPꢓꢃꢀꢄꢋꢀꢀꢃ
ꢉ&+ 8+ ꢊꢅꢃꢌꢁꢋꢒꢏꢃꢉ8+ &+ ꢊꢅꢃꢀꢀꢆꢋꢀꢎꢃꢉ&+ꢊꢅꢃꢀꢆꢌꢋꢂꢌꢃ
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ꢉ&2ꢊꢋꢃ)RXQGꢓꢃ0 ꢃꢆꢄꢒꢋꢁꢄꢇꢎꢋꢃ& + 12 6ꢋꢃ&DOFXODWHGꢓꢃ
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+DWDꢅꢃ 7ꢋꢅꢃ -DNXERZVNLꢅꢃ $ꢋ$ꢋꢅꢃ 6SULQJVꢅꢃ (ꢋ%ꢋꢅꢃ DQGꢃ 7LVKꢈꢃ
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YROꢋꢃ ꢆꢅꢃ Sꢋꢃ ꢂꢆꢇꢐꢃ &R[ ꢅꢃ 0ꢋ2ꢋꢃ DQGꢃ 3UDJHUꢅꢃ 5ꢋ+ꢋꢅꢃ$XVWꢁ -ꢁ
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ZDLꢅꢃ$ꢋꢅꢃ0DWVXLꢅꢃ7ꢋꢅꢃ+DUDꢅꢃ2ꢋꢅꢃDQGꢃ6KLRLULꢅꢃ7ꢋꢅꢃ7HWUDKHGURQꢅꢃ
ꢀꢒꢒꢁꢅꢃYROꢋꢃꢄꢌꢅꢃSꢋꢃꢄꢏꢆꢂꢋꢃ
ꢀꢏꢋꢃ $QGHUVRQꢅꢃ*ꢋ:ꢋꢅꢃ=LPPHUPDQꢅꢃ-ꢋ(ꢋꢅꢃDQGꢃ&DOODKDQꢅꢃ)ꢋ0ꢋꢅꢃ
-ꢁ $Pꢁ &KHPꢁ 6RFꢋꢅꢃꢀꢒꢌꢄꢅꢃYROꢋꢃꢏꢌꢅꢃSꢋꢃꢀꢏꢂꢒꢋꢃ
ꢀꢒꢋꢃ &RXWXUHꢅꢃ$ꢋꢅꢃ *UDQGFODXGRQꢅꢃ 3ꢋꢅꢃ +RDUDXꢅꢃ &ꢋꢅꢃ &RUQHWꢅꢃ -ꢋꢅꢃ
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YROꢋꢃꢌꢎꢅꢃSꢋꢃꢂꢌꢁꢀꢋꢃ
ꢎꢋꢃYRQꢃ 6FK|OONRSIꢅꢃ 8ꢋꢃ DQGꢃ 6FKU|GHUꢅꢃ 5ꢋꢅꢃ $QJHZꢁ &KHPꢋꢅꢃ
ꢀꢒꢎꢀꢅꢃYROꢋꢃꢏꢂꢅꢃSꢋꢃꢂꢇꢏꢋꢃ
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