Staudinger and retro-Staudinger reactions. The dichloro-β-lactam moiety as a useful handle for the synthesis of 4-aryl-2H-1,3-benzothiazine 1,1-dioxides

Tetrahedron Letters

Volumn 51, Issue 24, 2010, Pages 3205-3207

  Fodor, Lajos ^a,b   Csomós, Péter ^a,b   Csámpai, Antal ^c   Sohár, Pál ^c  

^a UNIVERSITY OF SZEGED   (Hungary)

^b Department of Pediatrics   (Hungary)

^c EÖTVÖS LORÁND UNIVERSITY   (Hungary)

Author keywords

1,3 Benzothiazine; Dichloro lactam; Oxidation; Staudinger reaction

Indexed keywords

1,1 DICHLOROAZETO[2,1 C][1,3]BENZOTHIAZIN 2 ONE DERIVATIVE; 2H 1,3 BENZOTHIAZINE 1,1 DIOXIDE DERIVATIVE; BENZOTHIAZINE DERIVATIVE; BETA LACTAM DERIVATIVE; THIAZINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; OXIDATION; REACTION ANALYSIS; RETRO STAUDINGER REACTION; STAUDINGER REACTION; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 77953233076     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.04.051     Document Type: Article

References (30)

1. Brieaddy, L. E. WO Patent 9316055, 1993; Chem. Abstr. 1994, 120, 164244.
2. Brieaddy, L. E. WO Patent 9605188, 1996; Chem. Abstr. 1996, 125, 114724.
3. Sasahara, T.; Mohri, M. WO Patent 2004/020421, 2004; Chem. Abstr. 2004, 140, 253584.
4. Starke, I.; Alenfalk, S.; Nordberh, M. P.; Dahlstrom, M. U. J.; Bostrom, S. J.; Lemurell, M. A.; Wallberg, A. C. WO Patent 2004076430, 2004; Chem. Abstr. 2004, 141, 260784.
5. Kaneko, N. WO Patent 2005105793, 2005; Chem. Abstr. 2005, 143, 452896.
6. Marks, A. R.; Landry, D. W.; Deng, S.; Cheng, Z. Z.; Lehnart, S. E. WO Patent 2007024717, 2007; Chem. Abstr. 2007, 146, 295964.
7. Cali, P.; Hjelmencrantz, A.; Naerum, L. WO Patent 2005092872, 2005; Chem. Abstr. 2005, 143, 367310.
8. Richy F., Scarpignato C., Lanas A., and Reginster J.-Y. Pharmacol. Res. 60 (2009) 254
9. Zinnes H., Comes R.A., and Shavel J. J. Org. Chem. 29 (1964) 2068
10. Elghamry I., and Döpp D. Tetrahedron Lett. 42 (2001) 5651
11. Elghamry I., Döpp D., and Henkel G. J. Heterocycl. Chem. 44 (2007) 849
12. Szabó J., Szücs E., Fodor L., Katócs A., Bernáth G., and Sohár P. Tetrahedron 44 (1988) 2985
13. Fodor L., Szabó J., and Sohár P. Tetrahedron 37 (1981) 963
14. Fodor L., Szabó J., Bernáth G., Párkányi L., and Sohár P. Tetrahedron Lett. 22 (1981) 5077
15. Fodor L., Szabó J., Szu{combining double acute accent}cs E., Bernáth G., Sohár P., and Tamás J. Tetrahedron 40 (1984) 4089
16. Csomós P., Fodor L., Bernáth G., Sinkkonen J., Salminen J., Wiinamäki K., and Pihlaja K. Tetrahedron 64 (2008) 1002
17. Fodor L., Szabó J., Bernáth G., Sohár P., Argay G., Kálmán A., and Tamás J. Tetrahedron 44 (1988) 7180
18. Cossío F.P., Arrieta A., and Sierra M.A. Acc. Chem. Res. 41 (2008) 925
19. Xu J. Arkivoc ix (2009) 21
20. Fu N., and Tidwell T.T. Tetrahedron 64 (2008) 10465
21. 14 Yields, 4a: 97%, 4b: 95%, 4c: 88%.
22. Alcaide B., Almendros P., and Aragoncillo C. Chem. Rev. 107 (2007) 4437
23. Alcaide B., Almendros P., and Redondo M. Chem. Commun. (2006) 2616
24. Alcaide B., Aly M., Rodríguez C., and Rodríguez-Vicente A. J. Org. Chem. 65 (2000) 3453
25. Dejaegher Y., Mangelinkx P., and De Kimpe N. J. Org. Chem. 67 (2002) 2075
26. 4S (331.39): C, 61.61; H, 5.17; N, 4.23; S, 9.68. Found: C, 61.46; H, 5.33; N, 4.01; S, 9.87.
27. 5S (442.31): C, 51.59; H, 3.87; N, 3.17; S, 7.25. Found: C, 51.45; H, 4.10; N, 3.41; S, 7.08.
28. Holly S., and Sohár P. In: Láng L., and Prichard W.H. (Eds). Theoretical and Technical Introduction to the Series Absorption Spectra in the Infrared Region (1975), Akadémiai Kiadó, Budapest 113 (a) p 113; (b) pp 128-129
29. Wuts P.G.M., and Greene T.W. Protective Groups in Organic Synthesis (2007), Wiley Interscience, Hoboken, New Jersey
30. Szabó J., Fodor L., Szücs E., Bernáth G., and Sohár P. Pharmazie 39 (1984) 426