Synthesis of the new (cyclopenta[b]pyrrolo[1,2-d])azepino[4,5-b]indole ring system

Tetrahedron Letters

Volumn 37, Issue 32, 1996, Pages 5701-5704

  Noé, Eric ^a,b   Séraphin, Denis ^a   Zhang, Qiang ^a   Djaté, Frédéric ^a   Hénin, Jacques ^a   Laronze, Jean Yves ^a   Lévy, Jean ^a  

^a UNIVERSITÉ DE REIMS CHAMPAGNE ARDENNE   (France)

^b INSTITUT DE RECHERCHE PIERRE FABRE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

INDOLE DERIVATIVE; PYRROLE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0030570897     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01215-4     Document Type: Article

References (17)

1. 4. Gauvin-Hussenet, C.; Séraphin, D.; Cartier, D.; Laronze, J.Y.; Lévy, J. Tetrahedron Lett., 1993, 34, 465-468.
2. 5. Duhamel, L.; Duhamel, P.; Collet, C.; Haider, A.; Poirier, J.M. Tetrahedron Lett., 1972, 4743-4746.
3. 6. Buzas, A.; Retourne, C. Heterocycles, 1977, 6, 1307-1310.
4. 7. Costa, G.; Riche, C.; Husson, H.P. Tetrahedron, 1977, 33, 315-320.
5. 8. Obtained by chromic oxidation of 3-methyl-1-formylcyclohex-3-ene (ref.4) and esterification by MeOH-HCl.
6. 13C NMR, HRMS or elemental analysis.
7. 10. Prepared in two steps as follows : i : Na 1 eq., EtOH, diethyl malonate 1 eq., r.t. 30 min then 2,3-dichloropropene 1.1 eq., r.t., 96 h; ii : NaH 1 eq., 1-bromo-3-chloropropane 1 eq., THF, reflux, 48 h; overall yield 64 %.
8. 11. 12a: mp 77°C; UV (MeOH) 229, 308, 318 nm
9. 2-CCl), 44.7 (C5), 37.5 (C1), 25.0 (C2), 22.4 (C6).
10. 2-CCl), 21.8 (C7), 16.5 (C3).
11. 2O, r.t., 2 h then reflux 4 h .
12. 15. Stevens, C.L.; Pillai, P.M. J. Am. Chem. Soc., 1967, 89, 3084-3085. Additional information on epoxyamine reactivity : Lluch, A.M.; Gibert, M.; Sanchez-Baeza, F.; Messeguer, A. Tetrahedron, 1996, 52, 3973-3982, and ref. cited.
13. 15. Stevens, C.L.; Pillai, P.M. J. Am. Chem. Soc., 1967, 89, 3084-3085. Additional information on epoxyamine reactivity : Lluch, A.M.; Gibert, M.; Sanchez-Baeza, F.; Messeguer, A. Tetrahedron, 1996, 52, 3973-3982, and ref. cited.
14. 16. Pierron, C.; PhD Thesis, Université de Reims Champagne-Ardenne, 1970.
15. 2), 31.9 (C2), 22.5 (C3), 17.9 (C7).
16. 18. Bohlmann, F. Ber., 1958, 91, 2157-2167.
17. 3) δ 216.1 (C2), 135.2 (C13a), 133.1 (C14a), 129.0 (C9b), 121.6 (C12), 119.2 (C11), 118.0 (C10), 111.1 (C9a), 110.4 (C13), 69.8 (C-3a), 53.2 (C6), 46.1 (C8), 45.9 (C14b), 45.8 (C3), 45.7 (C1), 40.8 (C4), 23.7 (C5), 21.7 (C9).