Unexpected facile sequential halolactamization-hydroxylation of 2, 3-allenamides with CuX(2) for the efficient synthesis of 4-halo-5-hydroxypyrrol-2(5H)-ones.
[reaction: see text] 4-Halo-5-hydroxypyrrol-2(5H)-ones were synthesized from the efficient sequential halolactamization-hydroxylation reaction of 4-monosubstituted 2,3-allenamides with CuX(2) (X = Br, Cl) in high yields. Halolactamization of fully substituted 2,3-dienamide (1f) afforded 4-halo-pyrrol-2(5H)-ones.
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Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, P. R. China. masm@pub.sioc.ac.cn
Xie
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D000577:Amides / Q000737:chemistry; D000970:Antineoplastic Agents / Q000138:chemical synthesis; D002384:Catalysis; D003300:Copper; D006900:Hydroxylation; D007769:Lactams / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D011090:Polyenes / Q000737:chemistry; D011758:Pyrroles / Q000138:chemical synthesis*
D000577:Amides; D000970:Antineoplastic Agents; D007769:Lactams; D011090:Polyenes; D011758:Pyrroles; D003300:Copper