Platinum-catalyzed consecutive C-N bond formation-[1,3] shift of carbamoyl and ester groups

Tetrahedron Letters

Volumn 50, Issue 18, 2009, Pages 2075-2077

  Nakamura, Itaru ^a   Sato, Yusuke ^a   Konta, Sayaka ^a   Terada, Masahiro ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBANILAMIDE DERIVATIVE; ESTER DERIVATIVE; PLATINUM COMPLEX;

AMINATION; ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION;

EID: 62349119891     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.02.108     Document Type: Article

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31. 4 and 0.25 mmol of 1 was added 1.0 mL of ethyl acetate in a pressure vial (Wheaton v-vial) at room temperature, and the mixture was stirred at 100 °C. After complete consumption of the starting material, which was monitored by TLC, the reaction mixture was cooled to room temperature. The reaction mixture was passed through a short pad of silica gel with ethyl acetate. After the solvents were removed in vacuo, the residue was purified by silica-gel column chromatography using ethyl acetate/hexane (1:5) as eluent. The obtained mixture of 2 and 5 was separated by gel permeation chromatography (Japan Analytical Industry Co. LC-918) to give product 2.
32. The reaction of 3a with lower catalyst loading (5 mol %) took 20 h, affording 4a in 60% yield along with 21% of recovered 3a.