Synthesis of Imidazolidin-2-ones and Imidazol-2-ones via Base-Catalyzed Intramolecular Hydroamidation of Propargylic Ureas under Ambient Conditions

被引：21

作者：

Casnati, Alessandra ^{[1
]}

Perrone, Antonio ^{[1
]}

Mazzeo, Paolo P. ^{[1
,2
]}

Bacchi, Alessia ^{[1
,2
]}

Mancuso, Raffaella ^{[3
]}

Gabriele, Bartolo ^{[3
]}

Maggi, Raimondo ^{[1
]}

Maestri, Giovanni ^{[1
]}

Motti, Elena ^{[1
]}

Stirling, Andras ^{[4
]}

Della Ca', Nicola ^{[1
]}

机构：

[1] Univ Parma, Dept Chem Life Sci & Environm Sustainabil, I-43124 Parma, Italy

[2] Biopharmanet Tec, Parco Sci 27-A, I-43124 Parma, Italy

[3] Univ Calabria, Dipartimento Chim & Tecnol Chim, I-87036 Cosenza, Italy

[4] Res Ctr Nat Sci, Theoret Chem Res Grp, Inst Organ Chem, Budapest, Hungary

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 84卷 / 06期

关键词：

CYCLIC UREAS; OXIDATIVE CARBONYLATION; CESIUM HYDROXIDE; CARBON-DIOXIDE; MEDIATED HYDROAMINATION; ASYMMETRIC-SYNTHESIS; EFFICIENT SYNTHESIS; ALKYNES; AMINES; DIAMINES;

D O I：

10.1021/acs.joc.9b00064

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first organo-catalyzed synthesis of imidazolidin-2-ones and imidazol-2-ones via intramolecular hydroamidation of propargylic ureas is reported. The phosphazene base BEMP turned out to be the most active organo-catalyst compared with guanidine and amidine bases. Excellent chemo- and regioselectivities to five-membered cyclic ureas have been achieved under ambient conditions, with a wide substrate scope and exceptionally short reaction times (down to 1 min). A base-mediated isomerization step to an allenamide intermediate is the most feasible reaction pathway to give imidazol-2-ones, as suggested by DFT studies.

引用

页码：3477 / 3490

页数：14

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