The synthesis of 3-(dimethylamino)methyl-5H,11H-pyrrolo[2,1- c][1,4]benzothiazepine derivatives 2a-c which might show significant central nervous system (CNS) activity, is described. The basic side chain was introduced by a Mannich condensation with the preformed heterocyclic systems 1a-c. Synthesis of novel 5-phenyl-5H,11H-pyrrolo[2,1-c][1,4]benzothiazepine le by a nucleophilic aromatic fluoride displacement-cyclization and an attempted alternative route to le via a Pummerer rearrangement-cyclization are also reported. A mechanism for an unexpected formation of a pyrrole-2- carbaldehyde is proposed, as well.
Garofalo, A., Campiani, G., Ciani, S.M., Fiorini, I., Nacci, V. (1996). Polycondensed heterocycles. IX. Pyrrolo[2,1-c][1,4]benzothiazepines. Synthesis of 3-(dimethylamino)methyl derivatives. TETRAHEDRON, 52(22), 7745-7754 [10.1016/S0040-4020(96)00342-0].
Polycondensed heterocycles. IX. Pyrrolo[2,1-c][1,4]benzothiazepines. Synthesis of 3-(dimethylamino)methyl derivatives
Campiani, Giuseppe;Fiorini, Isabella;Nacci, Vito
1996-01-01
Abstract
The synthesis of 3-(dimethylamino)methyl-5H,11H-pyrrolo[2,1- c][1,4]benzothiazepine derivatives 2a-c which might show significant central nervous system (CNS) activity, is described. The basic side chain was introduced by a Mannich condensation with the preformed heterocyclic systems 1a-c. Synthesis of novel 5-phenyl-5H,11H-pyrrolo[2,1-c][1,4]benzothiazepine le by a nucleophilic aromatic fluoride displacement-cyclization and an attempted alternative route to le via a Pummerer rearrangement-cyclization are also reported. A mechanism for an unexpected formation of a pyrrole-2- carbaldehyde is proposed, as well.File | Dimensione | Formato | |
---|---|---|---|
Tetrahedron_1996.pdf
non disponibili
Tipologia:
Post-print
Licenza:
NON PUBBLICO - Accesso privato/ristretto
Dimensione
496.58 kB
Formato
Adobe PDF
|
496.58 kB | Adobe PDF | Visualizza/Apri Richiedi una copia |
I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
https://hdl.handle.net/11365/31315
Attenzione
Attenzione! I dati visualizzati non sono stati sottoposti a validazione da parte dell'ateneo