Synthesis and Transition Metal Catalysed Reactions of 1-Ureido-3-Propargyl-2,3-Dihydropyrrol-2-ols, 1-Ureido-3-Propargylpyrroles and 1-Ureido-3-Propargyl-3-Phosphono-1H-Pyrrol-2(3H)-ones

详细信息    查看全文

• 作者：Arcadi ; Antonio ; Attanasi ; Orazio A. ; De Crescentini ; Lucia ; Rossi ; Elisabetta ; Serra-Zanetti ; Franco
• 刊名：Tetrahedron
• 出版年：1996
• 出版时间：March 11, 1996
• 年：1996
• 卷：52
• 期：11
• 页码：3997-4012
• 全文大小：670 K

文摘

The title compounds were obtained by reaction of conjugated azoalkenes with activated methinic derivatives bearing a propargylic residue. 1-Ureido-3-propargyl-2,3-dihydropyrrol-2-ols gave in the presence of Cu(I) catalyst the 2,5-dimethyl-3-ethoxycarbonyl-4-(2-oxopropyl)-1-(N′-phenylureido)-pyrrole, while in the presence of Pd(0) or Au³⁺ the 3,6-dimethyl-5-ethoxycarbonyl-4-propargyl-1,4-dihydropyridazine was obtained by ring opening and ring expansion reaction. The propargylic side chain of 1-ureido-3-propargylpyrroles and 1-ureido-3-propargyl-3-phosphono-1H-pyrrol-2(3H)-ones was functionalised by means of palladium and/or copper catalysed coupling reactions with aryl or vinyl triflates and halides.