A New Method for the Synthesis of Imidazolidinone- and Benzimidazolone-containing [2.2]Cyclophanes

Organic Letters

Volumn 2, Issue 24, 2000, Pages 3785-3788

  Ellis, Keisha K ^a   Wilke, Burkhardt ^a   Zhang, Yuegang ^a   Diver, Steven T ^a  

^a UNIVERSITY AT BUFFALO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0010466194     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0064866     Document Type: Article

References (31)

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5. Imidazole-containing macrocycles: (a) Müller, F.; Mattay, J. Angew. Chem., Int. Ed. Engl. 1992, 31, 209.
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9. (e) Sasaki, S.-i.; Mizuno, M.; Naemura, K.; Tobe, Y. J. Org. Chem. 2000, 65, 275. Benzimidazole-containing macrocycles:
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14. Pye, P. J.; Rossen, K.; Reamer, R. A.; Tsou, N. N.; Volante, R. P.; Reider, P. J. J. Am. Chem. Soc. 1997, 119, 6207.
15. Heterophanes are [2.2]cyclophanes that contain at least one heterocyclic ring system. In cyclophane nomenclature, [m.n] refer to the number of atoms in the bridge between the two ring systems. The para descriptor is omitted because it is not appropriate with regard to the heterocyclic nucleus; the sites of substitution on the heterocycle are denoted in parentheses, see: Paudler, W. W.; Bezoari, M. D. Synthesis and Properties of Heterophanes. In Cyclophanes, Vol. 2; Keehn, P. M., Rosenfeld, S. M., Eds.; Academic Press: New York, 1983.
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19. The use of N-acyl iminium ions in synthesis: Speckamp, W. N.; Hiemstra, H. Tetrahedron 1985, 41, 4367.
20. 3) by syringe pump addition (12 h) to give the products C (eq 1) in 26% and 20% yields, respectively. The combination NaOH/EtOH gave ethoxy substitution product in the benzimidazolone series in contrast with successful literature macrocyclizations employing benzylic dihalides (ref 6). This latter observation led us to consider the source of the presumably greater reactivity in benzimidazolone dichlorides. Preparation of dihalides: (a) Petersen, H.; Reuther, W. Liebigs Ann. Chem. 1972, 766, 58.
21. (b) Zinner, H.; Spangenberg, B. Chem. Ber. 1958, 91, 1432.
22. Kimbonguila, A. M.; Merzouk, A.; Guibe, F.; Loffet, A. Tetrahedron Lett. 1994, 35, 9035.
23. 2) = 1.051. The racemate 5b was separated by HPLC using a chiral column (Chiracel OD-H, 4.6 mm x 30 cm, 10% IPA-hex, rt 10.01, 32.65 min). When pure enantiomer was collected and reinjected, there was no evidence of racemization. Heating 5b in pyridine (reflux, 1 h) did not result in racemization. Further studies of conformational issues are ongoing.
24. (a) Cram, D. J.; Montgomery, C. S.; Knox, G. R. J. Am. Chem. Soc. 1966, 88, 515.
25. (b) Timko, J. M.; Cram, D. J. J. Am. Chem. Soc. 1974, 96, 7159.
26. Haley, J. F., Jr.; Keehn, P. M. Tetrahedron Lett. 1973, 4017.
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29. 2) = 0.954. Absolute configuration could not be determined due to a lack of heavy atoms.
30. [2.2]Paracyclophane is estimated to have 31 kcal/mol ring strain. Cram, D. J.; Cram, J. M. Acc. Chem. Res. 1971, 4, 204.
31. For the parent [2.2]paracyclophane, the distortion angle is reported to be θ = 12°. See ref 16.