Synthesis of 1,4-diaza-7-oxabicyclo[4.3.0]non-2-en-6-ones by cyclization of 1,1-bis(trimethylsiloxy)ketene acetals with pyrazine and quinoxaline

Tetrahedron

Volumn 62, Issue 51, 2006, Pages 12084-12091

  Rotzoll, Sven ^a,b   Ullah, Ehsan ^a,b,c   Fischer, Christine ^b   Michalik, Dirk ^b   Spannenberg, Anke ^b   Langer, Peter ^a,b  

^a UNIVERSITY OF ROSTOCK   (Germany)

^b LEIBNIZ INSTITUT FÜR KATALYSE E V AN DER UNIVERSITÄT ROSTOCK   (Germany)

^c UNIVERSITY OF GREIFSWALD   (Germany)

Author keywords

Cyclizations; Heterocycles; Iminium salts; Pyrazine; Quinoxaline; Silyl enol ethers

Indexed keywords

2 OXO 3,3A DIHYDROFURO[2,3 B]QUINOXALINE; 6 OXO 7,7A DIHYDROFURO[3,2 B]PYRAZINE; ACETAL DERIVATIVE; DIMETHYL 3 (2 CYCLOHEXYLETHYL) 2 OXO 3,3A DIHYDROFURO[2,3 B]QUINOXALINE 4,9(2H,9AH) DICARBOXYLATE; DIMETHYL 3 (CYCLOPENTYLMETHYL) 2 OXO 3,3A DIHYDROFURO[2,3 B]QUINOXALINE 4,9(2H,9AH) DICARBOXYLATE; DIMETHYL 3 BUTYL 2 OXO 3,3A DIHYDROFURO[2,3 B] QUINOXALINE 4,9(2H,9AH) DICARBOXYLATE; DIMETHYL 3 CYCLOHEXYL 2 OXO 3,3A DIHYDROFURO[2,3 B]QUINOXALINE 4,9(2H,9AH) DICARBOXYLATE; DIMETHYL 3 DODECYL 2 OXO 3,3A DIHYDROFURO[2,3 B]QUINOXALINE 4,9(2H,9AH) DICARBOXYLATE; DIMETHYL 3 ETHYL 2 OXO 3,3A DIHYDROFURO[2,3 B]QUINOXALINE 4,9(2H,9AH) DICARBOXYLATE; DIMETHYL 3 ISOPROPYL 2 OXO 3,3A DIHYDROFURO[2,3 B]QUINOXALINE 4,9(2H,9AH) DICARBOXYLATE; DIMETHYL 3 PROPYL 2 OXO 3,3A DIHYDROFURO[2,3 B]QUINOXALINE 4,9(2H,9AH) DICARBOXYLATE; DIMETHYL 7 BUTYL 6 OXO 7,7A DIHYDROFURO[3,2 B]PYRAZINE 1,4(4AH,6H) DICARBOXYLATE; DIMETHYL 7 CYCLOHEXYL 6 OXO 7,7A DIHYDROFURO[3,2 B]PYRAZINE 1,4(4AH,6H) DICARBOXYLATE; DIMETHYL 7 DODECYL 6 OXO 7,7A DIHYDROFURO[3,2 B]PYRAZINE 1,4(4AH,6H) DICARBOXYLATE; DIMETHYL 7 ETHYL 6 OXO 7,7A DIHYDROFURO[3,2 B] PYRAZINE 1,4(4AH,6H) DICARBOXYLATE; DIMETHYL 7 ISOPROPYL 6 OXO 7,7A DIHYDROFURO[3,2 B]PYRAZINE 1,4(4AH,6H) DICARBOXYLATE; DIMETHYL 7 PROPYL 6 OXO 7,7A DIHYDROFURO[3,2 B]PYRAZINE 1,4(4AH,6H) DICARBOXYLATE; PYRAZINE; QUINOXALINE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CYCLIZATION; POLYMERIZATION; PRIORITY JOURNAL; REACTION ANALYSIS; STOICHIOMETRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 33750695236     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.09.072     Document Type: Article

References (32)

1. Brook M.A. Silicon in Organic, Organometallic, and Polymer Chemistry (1999), Wiley-Interscience, New York, NY
2. Mukaiyama T., Banno K., and Narasaka K. J. Am. Chem. Soc. 96 (1974) 7503
3. Mukaiyama T. Org. React. 28 (1982) 203
4. Takai K., and Heathcock C.H. J. Org. Chem. 50 (1985) 3247
5. Bellassoued M., Chelain E., Collot J., Rudler H., and Vaissermann J. Chem. Commun. (1999) 187
6. Rudler H., Comte V., Garrier E., Bellassoued M., Chelain E., and Vaissermann J. J. Organomet. Chem. 621 (2001) 284
7. Rudler H., Harris P., Parlier A., Cantagrel F., Denise B., Bellassoued M., Chelain E., and Vaissermann J. J. Organomet. Chem. 624 (2001) 186
8. Rudler H., Harris A., Cantagrel F., and Bellassoued M. Chem. Commun. (2000) 771
9. Rudler H., Alvarez C., Parlier A., Perez E., Denise B., Xu Y., and Vaissermann J. Tetrahedron Lett. 45 (2004) 2409
10. Ullah E., and Langer P. Synlett (2004) 2782
11. Ullah E., and Langer P. Synthesis (2005) 3189
12. Scriven E.F.V. Pyridines and their Benzo Derivatives: (ii) Reactivity at Ring Atoms. In: Boulton A.J., and McKillop A. (Eds). In: Katritzky A.R., and Rees C.W. (Eds). Comprehensive Heterocyclic Chemistry Vol. 2 (1984), Elsevier Science, Oxford Part 2A, Chapter 2.05, p 165
13. Bradley W., and Jeffrey S. J. Chem. Soc., Chem. Commun. (1954) 2770
14. Diaba F., Le Houerou C., Grignon-Dubios M., and Gerval P. J. Org. Chem. 65 (2000) 907
15. Yamaguchi R., Hatano B., Nakaysau T., and Kozima S. Tetrahedron Lett. 38 (1997) 403
16. Akiba K., Nishihara Y., and Wada M. Tetrahedron Lett. 24 (1983) 5269
17. Diaba F., Le Houerou C., Grignon-Dubois M., Rezzonico B., and Gerval P. Eur. J. Org. Chem. (2000) 2915
18. Itoh T., Nagata K., Miyazaki M., Kameoka K., and Ohsawa A. Tetrahedron 57 (2001) 8827
19. Katritzky A.R., Zhang S., Kurz T., and Wang M. Org. Lett. 3 (2001) 2807
20. Comins D.L., Sandelier M.J., and Grillo T.A. J. Org. Chem. 66 (2001) 6829
21. Yadav J.S., Reddy B.V.S., Gupta M.K., Prabhakar A., and Jagadeesh B. Chem. Commun. (2004) 2124
22. Review:. Langer P. Synthesis (2002) 441
23. Schmidt A., Gütlein J.-P., Preuss A., Albrecht U., Reinke H., and Langer P. Synlett (2005) 2489
24. Rudler H., Denise B., Parlier A., and Daran J.-C. Chem. Commun. (2002) 940
25. Rudler H., Denise B., Parlier A., and Daran J.-C. Eur. J. Org. Chem. (2005) 3724
26. Ullah E., Rotzoll S., Schmidt A., Michalik D., and Langer P. Tetrahedron Lett. 46 (2005) 8997
27. Rudler H., Denise B., Xu Y., and Vaissermann J. Tetrahedron Lett. 46 (2005) 3449
28. Rychlewska U., Broom M.B.H., Eggleston D.S., and Hodgson D.J. J. Am. Chem. Soc. 107 (1985) 4768
29. Patel T.V.B., Misra A.N., and Manfatia Y.S. Pharmazie 54 (1999) 448 and references cited therein
30. Ainsworth C., and Kuo Y.-N. J. Organomet. Chem. 46 (1972) 73
31. Wissner A. J. Org. Chem. 44 (1979) 4617
32. CCDC-611764 contains all crystallographic details of this publication and is available free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html or can be ordered from the following address: Cambridge Crystallographic Data Centre, 12 Union Road, GB-Cambridge CB21EZ. Fax: +44 1223 336 033; or deposit@ccdc.cam.ac.uk.