Novel synthesis of benzothiazole derivatives via directed lithiation and aryne-mediated cyclization followed by quenching with electrophiles

Journal of Organic Chemistry

Volumn 61, Issue 15, 1996, Pages 5130-5133

  Stanetty, Peter ^a   Krumpak, Barbara ^a  

^a VIENNA UNIVERSITY OF TECHNOLOGY   (Austria)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001122493     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960203z     Document Type: Article

References (21)

1. Huisgen, R.; König, H.; Lepley, A. L. Chem. Ber. 1960, 93, 1496. Huisgen, R.; Sauer, J. Angew. Chem. 1960, 72, 91.
2. Huisgen, R.; König, H.; Lepley, A. L. Chem. Ber. 1960, 93, 1496. Huisgen, R.; Sauer, J. Angew. Chem. 1960, 72, 91.
3. Bunnett, J. F.; Hrutfiord, B. F. J. Am. Chem. Soc. 1961, 83, 1691.
4. Kessar, S. V. Acc. Chem. Res. 1978, 11, 283.
5. Kessar, S. V.; Pal, D.; Singh, M. Tetrahedron 1973, 29, 177.
6. Clark, R. D.; Caroon, J. M. J. Org. Chem. 1982, 2804.
7. Reavill, D. R.; Richardson, St. K. Synth. Commun. 1990, 20, 1423.
8. Sielecki, T. M.; Meyers, A. I. J. Org. Chem. 1992, 57, 3673.
9. Gschwend, H. G.; Rodriguez, H. R. Org. React. 1979, 26, 1. Snieckus, V. Chem. Rev. 1990, 90, 879.
10. Gschwend, H. G.; Rodriguez, H. R. Org. React. 1979, 26, 1. Snieckus, V. Chem. Rev. 1990, 90, 879.
11. General procedures: Beaver, D. J.; Roman, D. P.; Stoffel, P. J. J. Am. Chem. Soc. 1957, 79, 1236. Hodgkins, J. E.; Reeves, W. P. J. Org. Chem. 1964, 29, 3098. 3-Fluorophenyl isothiocyanate: Browne, D. W.; Dyson, G. M. J. Chem. Soc. 1931, 3285. 3-Chlorophenyl isothiocyanate: Hofmann, A. W. Chem. Ber. 1880, 13, 8.
12. General procedures: Beaver, D. J.; Roman, D. P.; Stoffel, P. J. J. Am. Chem. Soc. 1957, 79, 1236. Hodgkins, J. E.; Reeves, W. P. J. Org. Chem. 1964, 29, 3098. 3-Fluorophenyl isothiocyanate: Browne, D. W.; Dyson, G. M. J. Chem. Soc. 1931, 3285. 3-Chlorophenyl isothiocyanate: Hofmann, A. W. Chem. Ber. 1880, 13, 8.
13. General procedures: Beaver, D. J.; Roman, D. P.; Stoffel, P. J. J. Am. Chem. Soc. 1957, 79, 1236. Hodgkins, J. E.; Reeves, W. P. J. Org. Chem. 1964, 29, 3098. 3-Fluorophenyl isothiocyanate: Browne, D. W.; Dyson, G. M. J. Chem. Soc. 1931, 3285. 3-Chlorophenyl isothiocyanate: Hofmann, A. W. Chem. Ber. 1880, 13, 8.
14. General procedures: Beaver, D. J.; Roman, D. P.; Stoffel, P. J. J. Am. Chem. Soc. 1957, 79, 1236. Hodgkins, J. E.; Reeves, W. P. J. Org. Chem. 1964, 29, 3098. 3-Fluorophenyl isothiocyanate: Browne, D. W.; Dyson, G. M. J. Chem. Soc. 1931, 3285. 3-Chlorophenyl isothiocyanate: Hofmann, A. W. Chem. Ber. 1880, 13, 8.
15. Larsen, C.; Jakobsen, P. Acta Chim. Scan. 1973, 27, 201. McCarthy, W. C.; Foss, L. E. J. Org. Chem. 1977, 42, 1508. Hagemann, H. In Houben-Weyl, Methoden der Organischen Chemie, Erweiterungs - und Folgebände zur 4. Auflage, Kohlensäurederivate; Georg Thieme Verlag: Stuttgart, 1993.
16. Larsen, C.; Jakobsen, P. Acta Chim. Scan. 1973, 27, 201. McCarthy, W. C.; Foss, L. E. J. Org. Chem. 1977, 42, 1508. Hagemann, H. In Houben-Weyl, Methoden der Organischen Chemie, Erweiterungs - und Folgebände zur 4. Auflage, Kohlensäurederivate; Georg Thieme Verlag: Stuttgart, 1993.
17. Larsen, C.; Jakobsen, P. Acta Chim. Scan. 1973, 27, 201. McCarthy, W. C.; Foss, L. E. J. Org. Chem. 1977, 42, 1508. Hagemann, H. In Houben-Weyl, Methoden der Organischen Chemie, Erweiterungs - und Folgebände zur 4. Auflage, Kohlensäurederivate; Georg Thieme Verlag: Stuttgart, 1993.
18. Katritzky, A. R.; Vanden Eynde, J.-J. J. Chem. Soc., Perkin Trans. 1, 1989, 639. Freund, H.; Arndt, H.; Rusch, R. Ger. 1,166,547, 1962; Chem. Abstr. 1962, 60, 16438e, no data given.
19. Katritzky, A. R.; Vanden Eynde, J.-J. J. Chem. Soc., Perkin Trans. 1, 1989, 639. Freund, H.; Arndt, H.; Rusch, R. Ger. 1,166,547, 1962; Chem. Abstr. 1962, 60, 16438e, no data given.
20. If the reaction was run with both educts yields are shown in Scheme 2.
21. If both educts (16, 17) were used, see Scheme 3 for yields.