Synthesis of a wakayin model compound: Oxidative formation of a new pyrrole ring in the indol-3-yl-indoloquinone system

Tetrahedron Letters

Volumn 39, Issue 42, 1998, Pages 7677-7678

  Zhang, Liming ^a   Cava, Michael P ^a   Rogers, Robin D ^a   Rogers, Lillian M ^a  

^a UNIVERSITY OF ALABAMA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

INDOLOQUINOLINE DERIVATIVE; NAPHTHOQUINONE; PYRROLE DERIVATIVE; TRYPTAMINE;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; OXIDATION; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0032532781     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01718-3     Document Type: Article

References (12)

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2. 2. Kokoshka, J. M.; Capson, T. L.; Holden, J. A.; Ireland, C. M.; Barrows, L. R. Anti-Cancer Drug 1996, 7(7), 758-65.
3. 3. Kita, Y.; Tohma, H.; Inagaki, M.; Hatanaka, K.; Yakura, T. J. Am. Chem. Soc. 1992, 114, 2175.
4. 4. White, J. D.; Yager, K. M.; Yajura, T. J. Am. Chem. Soc. 1994, 116, 1831.
5. 5. Nishiyama, S.; Cheng, J. F.; Tao, X. L.; Yamamura, S. Tetrahedron Lett. 1991, 32, 4151.
6. 6. Tao, X. L.; Cheng, J. F.; Nishiyama, S., Yamamura, S. Tetrahedron 1994, 50, 2017.
7. 7. Izawa, T.; Nishiyama, S.; Yamamura, S. Tetrahedron Lett. 1994, 35, 917.
8. 8. Sadanandan, E. V.; Pillai, S. K.; Lakshmikantham, M. V.; Billimoria, A. D.; Culpepper, J. S.; Cava, M. P. J. Org. Chem. 1995, 60, 1800-05.
9. 2: C.75.95; H, 5.06; N, 8.86. Found: C, 75.83; H, 5.04; N, 8.72.
10. 2: C, 76.36; H, 5.45; N, 8.48. Found: C, 76.24; H, 5.47; N, 8.38.
11. 6), δ 179.68, 174.95, 135.94, 134.14, 133.06, 132.78, 130.80, 130.12, 126.89, 126.73, 126.05, 125.64, 125.42, 122.41, 121.12, 119.54, 119.40, 119.24, 111.57, 106.41. MS m/z (rel. intensity), 137 (22.7), 163 (15.0), 200 (9.6), 227 (12.5), 269 (10.5), 297 (13.3), 326 (100). HRMS required 326.105528, found 326.104370.
12. 3, F(000)=680, crystal dimensions 0.22 × 0.40 × 0.55 mm. Tables of atom positions, thermal parameters and a complete listing of bond distances and angles have been deposited at Cambridge Crystallographic Data Center.