A rapid and efficient synthesis of a new pyrrolobenzodiazocines via an intramolecular Friedel-Crafts reaction

Tetrahedron Letters

Volumn 50, Issue 43, 2009, Pages 5884-5887

  BouzBouz, Samir ^a   Sanselme, Morgane ^b  

^a UNIVERSITÉ DE ROUEN   (France)

^b UNIVERSITÉ DE ROUEN   (France)

Author keywords

Acrylamide; Cyclisation; Eight membered ring; Friedel Crafts; Intramolecular; Pyrrole; Pyrrolobenzodiazocine

Indexed keywords

3,4 DIHYDROPYRROLO[1,2 F][1,6]BENZODIAZOCIN 2 ONE; ACRYLAMIDE DERIVATIVE; PYRROLE DERIVATIVE; PYRROLO[1,2 B][2,5]BENZODIAZOCINE; PYRROLO[1,2 F][1,6] BENZODIAZOCINE; PYRROLOBENZODIAZOCINE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CYCLIZATION; FRIEDEL CRAFTS REACTION; ISOMER; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; X RAY DIFFRACTION;

EID: 69749086640     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.07.145     Document Type: Article

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18. Compounds 1b-d were prepared in two steps from commercially available 4-methoxy or 4-chloro or 4-fluoro 2-nitrophenylaniline by thermal condensation with 2,5-dimethoxytetrahydrofurane in glacial acetic acid to give 1-(4-methoxy or 4-chloro or 4-fluoro 2-nitrophenyl)-1H-pyrrole, which was then reduced with ethanolic hydrazine hydrate in the presence of Raney nickel. Amine 1e was prepared by reduction of 1-(6-methyl 2-nitrophenyl)-1H-pyrrole in an ethanolic aqueous ammonium chloride solution in the presence of zinc. Amine 1a is commercially available from Aldrich.
19. Bouzbouz, S. Unpublished results.
20. 2/EtOAc).
21. -1): 3185 (NH), 1683 (CO).
22. -1): 3188 (NH), 1697 (CO). MS m/z: 226 (78), 211 (4) 197 (11), 183 (21), 169 (100), 156 (11), 143 (2), 129 (3), 115 (4), 91 (5), 77 (7), 65 (6).
23. Crystallographic data for 3a reported in this manuscript have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication nos. CCDC 728234 Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ, UK (fax: (+44) 1223 336 033; e-mail: deposit@ccdc.cam.ac.uk).
24. 6 at seven different temperatures from 293 to 352 K. These spectra show the broadening of the signals with increasing temperature, there is also the reduction in the intensity of signals from the minor atropoisomer their dispartion up to 352 K.
25. The spectra of compounds 2e and 3e and the spectra of the reaction followed by NMR are in the Supplementary data.