Novel 3-Substituted 3-Acylaminobenzo[b]furan-2(3H)-ones: Synthesis and Chemiluminescence Studies

Advanced Synthesis and Catalysis

Volumn 340, Issue 1, 1998, Pages 20-25

  Matuszczak, Barbara ^a  

^a UNIVERSITY OF INNSBRUCK   (Austria)

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EID: 2742542469     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (17)

1. for part III see: B. Matuszczak, Monatsh. Chem. 128 (1997) 945
2. a) K.-D. Gundermann, F. McCapra, 'Chemiluminescence in Organic Chemistry', Springer, 1987 and literature cited therein;
3. b) A. K. Campbell 'Chemiluminescence: Principles and Applications in Biology and Medicine', VCH, 1988 and literature cited therein.
4. B. Matuszczak, Monatsh. Chem. 127 (1996) 1291
5. B. Matuszczak, Pharmazie 51 (1996) 862
6. H. Oediger, R. Braden (Bayer AG Leverkusen), Ger. Offen. 2,162,717 (17.12.1971); Chem. Abstr. 79 (1973) 66817j
7. J. Köppen, D. Matthies, H. Schweim, Liebigs Ann. Chem. 1985, 2383
8. Formation of the dimeric product has also been observed by reaction of 3-acylaminobenzo[b]furan-2(3H)ones with sulfonyl chlorides in basic medium [10]. Moreover, Lofthouse et al. have described dimeric compounds type 6 as products in the chemiluminescence reaction of 3-alkoxycarbamoylbenzo[b]furan-2(3H)ones [15].
9. Due to the high reactivity of the N-acylimines (5) and the degradation during TLC, detection of these N-acylimines failed.
10. C. Mannich, G. Heilner, Chem. Ber. 55 (1922) 356
11. A. Vogt, PhD thesis, University of Hamburg (Germany), 1989
12. E. P. Kohler, M. Reimer, J. Am. Chem. Soc. 31 (1904) 163
13. F. Weygand, W. Steglich, I. Lengyel, F. Fraunberger, Chem. Ber. 99 (1966) 1932 and literature cited therein.
14. a) A. Schouteeten, Y. Christidis, G. Mattioda, Bull. Soc. Chim. Fr. 45 (1978) II248;
15. b) Y. Christidis, A. Schouteeten (Nobel Hoechst Chimie, Puteaux, Hauts-de-Seine), Ger. Offen. 2,640,615 (17.03.1977); Chem. Abstr. 87 (1977) 53589b
16. O. R. Hansen, R. Hammer, Acta Chem. Scand. 7 (1953) 1331
17. G. J. Lofthouse, H. Suschitzky, B. J. Wakefield, R. A. Whittaker, B. Tuck, J. Chem Soc. Perkin Trans. I 1979, 1634