Novel polar cycloaddition of 1,2-thiazinylium salt

Tetrahedron Letters

Volumn 40, Issue 1, 1999, Pages 95-96

  Shimizu, Hiroshi ^a   Hatano, Takashi ^a   Matsuda, Takayuki ^a   Iwamura, Tatsunori ^a  

^a GIFU PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 BUTADIENE; HETEROCYCLIC COMPOUND; ISOPRENE; PYRROLE DERIVATIVE;

ARTICLE; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; MOLECULAR INTERACTION;

EID: 0032890265     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)80028-2     Document Type: Article

References (10)

1. (a) H. Shimizu, S. Miyazaki, T. Kataoka, M. Hori and O. Muraoka, J. Chem. Soc., Perkin Trans. 1, 1994, 3129.
2. (b) H. Shimizu, S. Miyazaki, T. Kataoka and M. Hori, J. Chem. Soc., Perkin Trans. 1, 1995, 1583.
3. (c) H. Shimizu, S. Miyazaki and T. Kataoka, J. Chem. Soc., Perkin Trans. 1, 1996, 2227.
4. (d) H. Shimizu, S. Miyazaki and T. Kataoka, Tetrahedron, 1997, 53, 4611.
5. 3) δ: 7.26-7.33 (m, ArH), 7.50-7.61 (m, ArH), 7.61-7.72 (m, ArH), 7.74-7.88 (m, ArH), 7.89 (d, J=7 Hz, ArH), 8.27-8.50 (m, ArH), 10.43 (br. s, NH).
6. 3) δ: 16.9 (q), 20.0 (q), 37.8 (t), 52.5 (t), 116.2 (s), 118.7 (d), 122.6 (s), 123.2 (s), 125.3 (s), 125.6 (d), 126.3 (s), 126.3 (d), 127.0 (d), 130.3 (d), 131.8 (d), 136.3 (d), 136.9 (s).
7. 3), 4.02 (d, J=16 Hz, SCHH), 4.16 (dd, J=7, 16 Hz, SCHH), 4.42 (d, J=19 Hz, NCHH), 4.54 (d, J=19 Hz, NCHH), 5.74 (d, J=7 Hz, CH=); for 3d, 8: 3.73 (dd, J=6, 16 Hz, NCHH), 3.79 (dd, J=16, 6 Hz, NCHH), 5.96 (br. S, CH=).
8. The calculation of the two cations 2 and 4 was performed with The PM3 hamiltonian by "WinMOPAC v1.0 (Fujitsu Ltd.) for Windows 95 (Microsoft Inc.)", which is based on the MOPAC93 of Dr. J.J.P. Stewart and Fujitsu Ltd., Tokyo Japan.
9. H. Shimizu, K. Ikedo, K Hamada, M. Ozawa, H. Matsumoto, K. Kamata, H. Nakamura, M. Ji, T. Kataoka and M. Hori, J. Chem. Soc., Perkin Trans, 1, 1991, 1733.
10. 3) 8: 9.7 (q), 10.6 (q), 120.2 (d), 121.0 (s), 121.7 (s), 123.9 (s), 124.3 (d), 125.8 (d), 128.4 (d), 128.6 (d), 129.0 (d), 131.2 (d), 131.4 (d), 131.7 (d), 135.2 (s), 137.7 (s), 139.3 (s), 142.8 (s):