Abstract
The sodium salts of o-sulfanylphenyl ketones 3a-g were treated with α-benzotriazol-1-ylalkyl chlorides 4a,b to give intermediates 5a-k in good yields. Compounds 5a-k, on treatment successively with LDA and Ti (0), gave benzothiophenes 7a-k.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
REFERENCES
B. Iddon; R. M. Scrowston, in: A. R. Katritzky and A. J. Boulton (eds.), Adv. Heterocycl. Chem., 11, Acad. Press, New York (1970), p. 177.
R. M. Kellogg, in: A. R. Katritzky and C. W. Rees (eds.), Comprehensive Heterocycl. Chem., 4, Pergamon Press, Oxford (1984), p. 713.
M. Szajda and J. N. Lam, in: A. R. Katritzky, C. W. Rees, and E. F. V. Scriven (eds.), Comprehensive Heterocycl. Chem., 2, Pergamon Press, Oxford (1996), p. 437.
R. D. Gilliom, W. P. Purcell, and T. R. Bosin, Eur. J. Med. Chem.-Chim. Ther., 12, 187 (1977); Chem. Abstr., 87, 62366d (1977).
D. Duterte-Boucher, J. M. Vaugeois, J. Costentin, A. Ilagouma, T. Maurice, J. Vignon, and J. M. Kamenka, Proc. Jt. Fr.-U.S. Semin, CNRS-NSF, 3 rd, 1991, 435; Chem. Abstr., 119, 241180q (1993).
W. H. W. Lunn, PCT Int. Appl. WO95 17,095; Chem. Abstr., 123, 339715 (1995).
S. H. Groen, R. M. Kellogg, J. Buter, and H. Wynberg, J. Org. Chem., 33, 2218 (1968).
T. Kitamura, S. Kobayashi, and H. Taniguchi, Chem. Lett., 1637 (1988).
W. Ando, T. Oikawa, K. Kishi, T. Saiki, and T. Migita, J. Chem. Soc., Chem. Commun., 704 (1975).
L. Benati, P. C. Montevecchi, and P. Spagnolo, J. Chem. Soc., Perkin Trans. 1, 1659 (1992).
G. Capozzi, G. Melloni, G. Modena, and M. Piscitelli, Tetrahedron. Lett., 4039 (1968).
G. Melloni and G. Modena, J. Chem. Soc., Perkin Trans. 1, 1355 (1972).
T. Sonoda, M. Kawakami, T. Ikeda, S. Kobayashi, and H. Taniguchi, J. Chem. Soc., Chem. Commun., 612 (1976).
H. Blatt, J. J. Brophy, L. J. Colman, and W. J. Tairych, Aust. J. Chem., 29, 883 (1976).
T. Higa and A. J. Krubsack, J. Org. Chem., 41, 3399 (1976).
S. Middleton, Aust. J. Chem., 12, 218 (1959).
B. L. Flynn, P. Verdier-Pinard, and E. Hamel, Org. Lett., 3, 651 (2001).
A. R. Katritzky, Y. Ji, Y. Fang, and I. Prakash, J. Org. Chem., 66, 5613 (2001).
A. R. Katritzky, W. Kuzmierkiewicz, B. Rachwal, S. Rachwal, and J. Thomson, J. Chem. Soc., Perkin Trans. 1, 811 (1987).
A. R. Katritzky and J. Li, J. Org. Chem., 62, 238 (1997).
L. E. Brieaddy and K. H. Donaldson, J. Heterocycl. Chem., 32, 1683 (1995).
D. Machii, S. Fujiwara, Y. Onoda, H. Takai, T. Sano, T. Ishikawa, S. Takahara, and K. Yamada, Jpn. Kokai Tokkyo Koho JP 06,145,150 [94, 145, 150]; Chem. Abstr., 122, 239700 (1995).
G. Holan, D. F. O'Keefe, and K. E. Jarvis, PCT Int. Appl. WO91 07,380; Chem. Abstr., 115, 135692 (1991).
D. Seyferth, W. Tronich, R. S. Marmor, and W. E. Smith, J. Org. Chem., 37, 1537 (1972).
S. Cabiddu, D. Cancellu, C. Floris, G. Gelli, and S. Melis, Synthesis, 888 (1988).
O. Dann and M. Kokorudz, Chem. Ber., 91, 173 (1958).
R. Leardini, D. Nanni, and G. Zanardi, J. Org. Chem., 65, 2763 (2000).
F. Effenberger and W. Russ, Chem. Ber., 115, 3719 (1982); Chem. Abstr., 98, 106904 (1985).
A. R. Katritzky, L. Serdyuk, and L. Xie, J. Chem. Soc., Perkin Trans. 1, 1059 (1998).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Katritzky, A.R., Kirichenko, K., Ji, Y. et al. Novel Syntheses of 2,3-Disubstituted Benzothiophenes. Chemistry of Heterocyclic Compounds 38, 156–164 (2002). https://doi.org/10.1023/A:1015331023769
Issue Date:
DOI: https://doi.org/10.1023/A:1015331023769