Oxidative cyclization of acyclic ureas with bis(trifluoroacetoxy)iodobenzene to generate N-substituted 2-benzimidazolinones

Tetrahedron Letters

Volumn 37, Issue 14, 1996, Pages 2361-2364

  Romero, Arthur G ^a   Darlington, William H ^a   Jacobsen, E Jon ^a   Mickelson, John W ^a,b  

^a PFIZER INC   (United States)

^b 3M COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZIMIDAZOLE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0029943732     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00291-2     Document Type: Article

References (10)

1. For example, nitration/reduction. For a superior one-pot method utilizing aryl carbanions (Li or Mg) and diphenylphosphoryl azide, see S. Mori, T. Aoyama, T. Shioiri, Tetrahedron Lett. 1984, 25, 429-432.
2. Perronner, J.; Demoute, J.-P. Gazz. Chim. Ital. 1982, 112, 507-511.
3. A related one-pot oxidative cyclization induced by lead tetraacetate has been reported. The cyclization substrates (similar to 17) possess a hydrogen substituent on the 3-N aryl substituted urea nitrogen: J.H. Cooley and P.T. Jacobs, J. Org. Chem. 1975, 40, 552-557.
4. All products were fully characterized and gave acceptable C,H,N analyses.
5. Bis(trifluoroacetoxy)iodobenzene has been used in a similar fashion to obtain cyclic N-methoxy lactams. Y. Kikugawa and M. Kawase, Chem. Lett. 1990, 581-582. For reviews of hypervalent iodine chemistry, see: R.M. Moriarty, O. Prakash, Acc. Chem. Res. 1986, 19, 244-250; A. Varvoglis, Synthesis 1984, 709-726.
6. Bis(trifluoroacetoxy)iodobenzene has been used in a similar fashion to obtain cyclic N-methoxy lactams. Y. Kikugawa and M. Kawase, Chem. Lett. 1990, 581-582. For reviews of hypervalent iodine chemistry, see: R.M. Moriarty, O. Prakash, Acc. Chem. Res. 1986, 19, 244-250; A. Varvoglis, Synthesis 1984, 709-726.
7. Bis(trifluoroacetoxy)iodobenzene has been used in a similar fashion to obtain cyclic N-methoxy lactams. Y. Kikugawa and M. Kawase, Chem. Lett. 1990, 581-582. For reviews of hypervalent iodine chemistry, see: R.M. Moriarty, O. Prakash, Acc. Chem. Res. 1986, 19, 244-250; A. Varvoglis, Synthesis 1984, 709-726.
8. Bis(trifluoroacetoxy)iodobenzene is prepared by carboxylic acid exchange, i.e. dissolving bis(acetoxy)iodobenzene in trifluoroacetic acid.
9. Other alkyloxy groups such as benzyloxy can be substituted for methoxy.
10. 3ONCO from the aryl nitrogen by loss of the adjacent C-H proton; this type of side product was not seen with cyclization precursor 13.