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.
1996
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].
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11365/31315
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