Intermolecular acetoxyaminoalkylation of α-diazo amides with (diacetoxyiodo)benzene and amines
Multicomponent reactions of diazo compounds have attracted much attention in recent years. Such transformations are generally conducted by applying transition metal catalysis and involve the corresponding metal carbenes as key intermediates. In this letter, a metal-free three-component intermolecular acetoxyaminoalkylation of α-diazo amides with tertiary aryl amines and (diacetoxyiodo)benzene is presented.
One-pot synthesis of 3-hydroxyquinolin-2(1 H)-ones from N-phenylacetoacetamide via PhI(OCOCF3)2-mediated α-hydroxylation and H2SO4-promoted intramolecular cyclization
A clean, one-pot synthesis of the biologically important 3-hydroxyquinolin-2(1H)-one compounds has been realized from the readily available N-phenylacetoacetamide derivatives through a PhI(OCOCF 3)2-mediated α-hydroxylation and a H 2SO4-promoted intramolecular condensation. The hydroxyl group in the generated α-hydroxylated intermediate can be well tolerated in the second H2SO4-promoted cyclization step.
Yuan, Yucheng,Yang, Rui,Zhang-Negrerie, Daisy,Wang, Junwei,Du, Yunfei,Zhao, Kang
p. 5385 - 5392
(2013/07/26)
Preparation of 3-Acetyl-2-hydroxyindoles via Rhodium Carbenoid Aromatic C-H Insertion
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Etkin, Nola,Babu, Suresh D.,Fooks, Catherine J.,Durst, Tony
p. 1093 - 1096
(2007/10/02)
ORGANOMETALLIC INDUCED SELF-CONDENSATION OF CARBOXAMIDES
N,N-Disubstituted carboxamides containing α-hydrogen atoms undergo self-condensation reaction simply on treatment with Grignard reagents or n-BuLi in THF at room temp.The reaction is considerably influenced by steric hindrance at the α-carbon and the condensing agent utilized.A possible Claisen-type mechanism is also reported.
Babudri, F.,Ciminale, F.,Nunno, L. Di,Florio, S.
p. 557 - 561
(2007/10/02)
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