Thieno[2,3-b]indoles can be synthesised in 70–80 % yield by the sulfoxide rearrangement of 2-(4′-aryloxybut-2′-ynylthio)-1-methylindoles. The substrates are prepared by phase-transfer-catalysed alkylation of 1-methylindoline-2-thione with 1-aryloxy-4-chlorobut-2-ynes.
KobayashiG., FurukawaS., MatsudaY., and NatsukiR., Yakugaku Zasshi, 1969, 89, 58.
4.
(a) OhmotoT., and KoikeK., Chem. Pharm. Bull., 1984, 32, 170; (b) M. Shimizu, M. Ishikawa, Y. Komoda, T. Nkajima, K. Yamaguchi and N. Yoneda, Chem. Pharm. Bull., 1984, 32, 463; (c) Y. Endo, K. Shudo, K. Furuhata, H. Ogura, S. Sakai, N. Aimi, Y. Hitotsuyanagi and Y. Koyama, Chem. Pharm. Bull., 1984, 32(1), 358; (d) N. Haider and E. Sotero, Chem. Pharm. Bull., 2002, 50, 1479; (e) S. Sakai, N. Aimi, K. Yamaguchi, Y. Hitotsuyonagi, C. Watanabe, K. Yokose, Y. Koyama, K. Shudo and A. Itai, Chem. Pharm. Bull., 1984, 32, 354.
5.
(a) KamijoS., and YamamotoY., J. Org. Chem., 2003, 68, 4764; (b) R.J. Sundberg, The Chemistry of Indoles, Academic Press, New York, 1970, pp. 438-439; (c) E. Yamanaka, M. One, S. Kasamatsu, N. Aimi and S. Sakai, Chem. Pharm. Bull., 1984, 32, 818.
6.
(a) TakadaS., and MakisumiY., Chem. Pharm. Bull., 1984, 32, 872; (b) S. Takada, N. Ishizuka, T. Sasatani, Y. Makisumi, H. Jyoyama, H. Hatakeyama, F. Asanuma and K. Hirose, Chem. Pharm. Bull., 1984, 32, 877.
7.
(a) MajumdarK.C., and ThyagarajanB.S., J. Chem. Soc., Chem. Commun., 1972, 83; (b) K.C. Majumdar and B.S. Thyagarajan Int. J. Sulfur Chem., 1972, 2A, 93; (c) B. El-Osta, K.C. Majumdar and B.S. Thyagarajan, J. Heterocycl. Chem., 1973, 10, 107; (d) K.C. Majumdar and P. Biswas, Tetrahedron, 1998, 54, 11 603; (e) K.C. Majumdar and B.S. Thyagarajan, Int. J. Sulfur Chem., 1972, 2A, 67.
8.
(a) MajumdarK.C., and ThyagarajanB.S., Int. J. Sulfur Chem.1972, 2A, 153; (b) J.B. Hillard, K.V. Reddy, K.C. Majumdar and B.S. Thyagarajan, J. Heterocycl. Chem., 1974, 11, 369.
9.
(a) MajumdarK.C., and GhoshS.K., Tetrahedron Lett., 2002, 43, 2123; (b) K.C. Majumdar and M. Ghosh, Tetrahedron, 2002, 58, 10 047; (c) K.C. Majumdar, U.K. Kundu and S. Ghosh, Tetrahedron., 2002, 58, 10309.
10.
(a) ThyagarajanB.S., HillardJ.B., ReddyK.V., and MajumdarK.C., Tetrahedron Lett., 1974, 23, 1999; (b) K.C. Majumdar and S.K. Chattopadhyay, J. Chem. Soc., Chem. Commun., 1987, 524; (c) K.C. Majumdar and S.K. Samanta, Tetrahedron Lett., 2002, 43, 2119; (d) K.C. Majumdar and G.H. Jana, J. Org. Chem., 1997, 62, 1506; (e) K.C. Majumdar, G.H. Jana and U. Das, J. Chem. Soc. Perkin Trans. 1, 1997, 1229.