[4++2]-Type polar cycloadditions of 2-benzothiopyrylium salt with alkenes-Reference-Cited by-同舟云学术

[4++2]-Type polar cycloadditions of 2-benzothiopyrylium salt with alkenes

Published:2000-03 Issue:13 Volume:41 Page:2161-2164
ISSN:0040-4039
Container-title:Tetrahedron Letters
language:en
Short-container-title:Tetrahedron Letters

Author:

Shimizu Hiroshi,Araki Naoko,Muraoka Osamu,Tanabe Genzoh

Publisher

Elsevier BV

Subject

Organic Chemistry,Drug Discovery,Biochemistry

Reference4 articles.

1. (a) Shimizu, H.; Miyazaki, S.; Kataoka, T.; Hori, M.; Muraoka, O. J. Chem. Soc., Perkin Trans. 1 1994, 3129. (b) Shimizu, H.; Miyazaki, S.; Kataoka, T.; Hori, M. J. Chem. Soc., Perkin Trans. 1 1995, 1583. (c) Shimizu, H.; Miyazaki, S.; Kataoka, T. J. Chem. Soc., Perkin Trans. 1 1996, 2227. (d) Shimizu, H.; Miyazaki, S.; Kataoka, T. Tetrahedron 1997, 53, 4611.

2. Shimizu, H.; Araki, N.; Muraoka, O.; Tanabe, G. J. Chem. Soc., Chem. Commun. 1996, 2185.

3. [4++2]-Type polar cycloadditions employing in situ generated arylthienium salts have been reported: (a) Tamura, Y.; Ishiyama, K.; Mizuki, Y.; Maeda, H.; Ishibashi, H. Tetrahedron Lett. 1981, 22, 3773. (b) Thakur, D. K.; Vankar, Y. D. Synthesis 1983, 223. (c) Wada, M.; Shigehisa, T.; Kitani, H.; Akiba, K. Tetrahedron Lett. 1983, 24, 1715.

4. Satisfactory analytical data were obtained for all new compounds. Relevant spectral data for 3a are as follows: 1H NMR (CDCl3, 400 Mz) δ: 1.76 (1H, ddd, J=2.4, 6.8, 13.2 Hz, CHH), 2.67 (1H, ddd, J=3.4, 9.8, 13.2 Hz, CHH), 3.18 (3H, s, OMe), 3.18 (1H, dd, J=6.8, 9.8 Hz, CHPh), 3.59 (1H, d, J=3.4 Hz, 4-H), 4.18 (1H, dd, J=2.4, 3.4 Hz, 1-H), 5.33 (1H, d, J=3.4 Hz, 3-H), 6.73 (2H, dd, J=2.0, 7.3 Hz, ortho-2H of phenyl ring), 7.12 (4H, m, ArH), 7.30 (3H, m, ArH); 13C NMR (CDCl3) δ: 39.6, 39.9, 40.2, 47.8, 55.9, 90.0, 121.9, 126.3, 127.2, 127.4, 127.5, 128.3, 129.2, 134.2, 142.3, 145.2.

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