The gramine route to the Diels-Alder adducts of indolo-2,3-quinodimethanes

Tetrahedron Letters

Volumn 40, Issue 42, 1999, Pages 7463-7467

  Diker, Khalid ^a   Döé de Maindreville, Michèle ^a   Royer, Daniel ^a   Le Provost, Fabien ^a   Lévy, Jean ^a  

^a UNIVERSITÉ DE REIMS CHAMPAGNE ARDENNE   (France)

Author keywords

Diels Alder reactions; Indoles; Polycyclic heterocyclic compounds; Quinonoid compounds

Indexed keywords

1,2,3,4 TETRAHYDROCARBAZOLE DERIVATIVE; GRAMINE; HETEROCYCLIC COMPOUND; INDOLE DERIVATIVE; POLYCYCLIC AROMATIC COMPOUND; QUINONE DERIVATIVE; TERPENE DERIVATIVE;

ARTICLE; CHEMICAL MODIFICATION; REACTION ANALYSIS; SYNTHESIS; THERMAL EXPOSURE;

BETULACEAE;

EID: 0033569868     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01349-0     Document Type: Article

References (15)

1. Diker, K.; Döé de Maindreville, M.; Lévy, J. Tetrahedron Lett. 1999, 40, 7459-7462.
2. 3) δ: 13.4, 19.9, 39.6, 40.1, 42.6, 61.5, 109.2, 111.1, 117.5, 119.1, 121.6, 125.6, 126.3, 128.3, 128.6, 128.7, 131.5, 135.8, 169.8, 177.4, 179.
3. Potter, A. J.; Storr, R. C. Tetrahedron Lett. 1994, 35, 5293-5296.
4. Mundy, B. F. Concepts in Organic Synthesis; M. Dekker: NY, 1979.
5. The respective structures were not attributed.
6. 6) δ: 13.9, 61.8, 112.3, 117.1, 120.5, 121.0, 122.1, 123.3, 125.4, 126.7, 128.8, 138.5, 138.8, 139.2, 142.2, 148.2, 167.0, 184.1, 184.7.
7. Modi, S. P.; Oglesby, R. C.; Archer, S. Organic Synthesis 1995, 72, 125-134.
8. 3) δ: 2.87 (s, 3H), 3.05 (s, 3H), 3.30-3.50 (m, 3H), 3.85 (s, 3H), 4.10-4.30 (m, 2H), 6.80 (m, 1H), 6.94 (s, 1H), 7.22 (d, J=9.0 Hz, 1H), 9.22 (s, 1H).
9. 3) δ: 21.3, 39.4, 39.5, 42.4, 48.8, 108.3, 111.1, 118.2, 119.8, 122.0, 126.5, 127.2, 127.3, 127.4, 128.4, 128.6, 129.0, 132.9, 135.0, 135.8, 140.5, 178.6, 179.6.
10. Pindur, U.; Haber, M. Heterocycles 1991, 32, 1463-1470.
11. 3) δ: 12.3, 20.0, 21.7, 24.7, 36.6, 40.5, 44.1, 107.4, 110.9, 117.7, 119.6, 121.3, 126.6, 135.3, 136.0, 177.8, 179.9.
12. 3) δ: 21.9, 32.9, 41.7, 42.0, 43.2, 44.0, 44.1, 54.1, 55.1, 55.6, 106.1, 111.3, 117.5, 118.7, 120.3, 126.2, 126.7, 127, 128.2, 134.9, 135.9, 136, 177.4, 179.6.
13. 3) δ 21.0, 21.9, 25.1, 33.8, 36.9, 39.7, 43.2, 50.4, 107.8, 111.2, 117.9, 119.5, 121.6, 126.4, 132.8, 135.7, 172.1, 179.5, 179.8.
14. Snyder, H. R.; Matteson, D. S. J. Chem. Soc. 1957, 2217-2221.
15. 3OD) δ: 41.6, 45.8, 47.6, 50.0, 54.1, 116.6, 116.9, 123.0, 123.9, 126.3, 130.8, 132.0, 132.2, 132.4, 132.7, 133.2, 133.5, 133.6, 134.1, 134.9, 141.3, 142.2, 143.0, 144.8, 146.1, 179.2, 179.8.