[4+1] Cycloaddition of N-acylimine derivatives with isocyanides: efficient synthesis of 5-aminooxazoles and 5-aminothiazoles

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• 作者：Takahiro Soetaup> ; up>up>soeta@se.kanazawa-u.ac.jp" class="auth_mailup> ; Kaname Tamura ; Yutaka Ukajiup> ; up>up>ukaji@staff.kanazawa-u.ac.jp" class="auth_mailup>
• 关键词：Isocyanide ; Aminooxazole ; Aminothiazole ; [4+1] Cycloaddition
• 刊名：Tetrahedron
• 出版年：6 May, 2014
• 年：2014
• 卷：70
• 期：18
• 页码：3005-3010
• 全文大小：535 K

文摘

[4+1] Cycloaddition reaction between isocyanides and N-acylimine derivatives generated from N-acyl N,O-acetals acting as isocyanophiles has been developed. These reactions proceeded smoothly and cleanly to afford the corresponding 5-aminooxazoles in high yields. This reaction was extended to the syntheses of 5-aminothiazoles by using N-thioacyl N,O-acetals. A wide range of N-acyl N,O-acetals, N-thioacyl N,O-acetals, and isocyanides were found to be applicable to this reaction.