Catalytic oxidative carbonylation of primary and secondary α,ω-diamines to cyclic ureas

Organic Letters

Volumn 1, Issue 7, 1999, Pages 961-964

  McCusker, Jennifer E ^a   Grasso, Cara A ^a   Main, Andrea D ^a   McEiwee White, Lisa ^a  

^a University of Florida ^*  (United States)

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[No Author keywords available]

Indexed keywords

EID: 0000391940     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990690f     Document Type: Article

References (37)

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34. 2 layer was concentrated and then taken up into methanol, while the red solid was rinsed with methanol. Both methanol fractions were combined and concentrated to obtain a yellow powder. The yellow powder was then sublimed to obtain a white solid (0.29 g, 40% yield, TON = 40). The solid was identified as 2-imidazolidinone by comparison with an authentic sample.
35. 3 (3.63 g, 26.4 mmol), and 140 equiv of iodine (3.02 g, 11.9 mmol). The vessel was then charged with 100 atm of CO and left to stir under pressure at room temperature for 24 h. The pressure was released, and the yellow solution was filtered away from a white solid and concentrated. The resulting pale yellow oil was dissolved in ethyl acetate and chromatographed on silica with ethyl acetate as eluent to obtain a colorless liquid (0.68 g, 47% yield, TON = 70). The liquid was identified as 1,3-dimethyl-2-imidazolidinone by comparison with an authentic sample.
36. McCusker, J. E.; Main, A. D.; Johnson, K. S.; Grasso, C. A.; McElwee-White, L. Manuscript in preparation.
37. These initial studies were carried out with substituted benzyl amines in which intramolecular reaction of the functional group with the amine was not possible. Studies of more complex substrates are in progress.