Cyclobutanone photoadducts of HCN and malononitrile: useful intermediates for the synthesis of C-nucleosides

Tetrahedron Letters

Volumn 48, Issue 15, 2007, Pages 2787-2789

  Mladenova, Gabriela ^a   Lee Ruff, Edward ^a  

^a YORK UNIVERSITY   (Canada)

Author keywords

C Nucleosides; Cyclobutanone; Oxacarbene; Photochemistry

Indexed keywords

C NUCLEOSIDE; CYCLOBUTANONE DERIVATIVE; MALONONITRILE; NUCLEOSIDE DERIVATIVE; PHOSPHATIDYLETHANOLAMINE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; PHOTOCHEMISTRY; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 33947144705     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.02.046     Document Type: Article

References (17)

1. Jeong L.S., and Lee J.A. Antivir. Chem. Chemoth. 15 (2004) 235-250
2. Lee-Ruff E., Xi F.-D., and Qie J.-H. J. Org. Chem. 61 (1996) 1547-1550
3. Khalili P., Naimi E., Knaus E.E., and Wiebe L.I. Biopharm. Drug Dispos. 23 (2002) 105-113
4. Lamberth C. Org. Prep. Proced. Int. 34 (2002) 151-167
5. Lee-Ruff E., Jiang J.-L., and Wan W.-Q. Tetrahedron Lett. 34 (1993) 261-264
6. Lee-Ruff E., Wan W.-Q., and Jiang J.-L. J. Org. Chem. 59 (1994) 2114-2118
7. Lee-Ruff E., Xi F.-D., and Qie J.H. J. Org. Chem 61 (1996) 1547-1550
8. Lee-Ruff E., Ostrowski M., Ladha A., Stynes D.V., Vernik I., Jiang J.-L., Wan W.-Q., Ding S.-F., and Joshi S. J. Med. Chem. 39 (1996) 5276-5280
9. Lee-Ruff E., and Margau R. Nucleos. Nucleot. Nucl. 20 (2001) 185-196
10. Zhong J.-H., Fishman A., and Lee-Ruff E. Organic Lett. 4 (2002) 4415-4417
11. Ghazi H., and Lee-Ruff E. J. Fluorine Chem. 126 (2005) 1565-1569
12. The insertion of siloxycarbenes, generated from acyl silanes, to HCN and malononitrile has been previously observed. Duff J.M., and Brook A.G. Can. J. Chem. 51 (1973) 2869-2883
13. 1H NMR; δ 2.23 (m, 1H), 2.59 (m, 1H), 2.87 (h, J = 7.92 Hz, 1H), 3.91 (t, J = 8.52, 8.04 Hz, 1H), 4.18 (t, J = 8.64, 7.64 Hz, 1H), 4.40 (dd, J = 7.24, 7.24 Hz, 1H), 4.47 (dd, J = 6.36, 6.36 Hz, 1H), 4.76 (dd, J = 5.64, 5.72 Hz, 1H), 7.48 (t, J = 7.68 Hz, 2H), 7.61 (t, J = 7.2 Hz, 1H), 8.07 (d, J = 7.68 Hz, 2H). Compounds 3 and 3′ as well as other photoproducts gave satisfactory elemental analyses.
14. Bio M.M., Xu F., Waters M., Williams J.M., Savary K.A., Cowden C.J., Yang C., Buck E., Song Z.J., Tschaen D.M., Volante R.P., Reamer R.A., and Grabowski E.J.J. J. Org. Chem. 69 (2004) 6257-6266
15. Miller D.D., Hamada A., Clark M.T., Adejare A., Patil P.N., Shams G., Romstedt K.J., Kim S.U., and Intrasuksri U. J. Med. Chem. 33 (1990) 1138-1144
16. Popsavin M., Torovic L., Spaic S., Stankov S., Kapor A., Tomic Z., and Popsavin V. Tetrahedron 58 (2002) 569-580
17. Mladenova G., and Lee-Ruff E. Chem. Rev. 103 (2003) 1449-1483