Synthesis of a New Series of N,N’-Dimethyltetrahydrosalen (H2 [H2Me]salen) Ligands by the Reductive Ring-Opening of 3,3'-Ethylene-bis(3,4-dihydro-6-substituted-2H-1,3-benzoxazines)

doi:10.3390/molecules15064102

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Molecules 2010, 15(6), 4102-4110; doi:10.3390/molecules15064102

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Synthesis of a New Series of N,N’-Dimethyltetrahydrosalen (H₂ [H₂Me]salen) Ligands by the Reductive Ring-Opening of 3,3'-Ethylene-bis(3,4-dihydro-6-substituted-2H-1,3-benzoxazines)

Augusto Rivera* , Jicli José Rojas, Jairo Salazar-Barrios, Mauricio Maldonado and Jaime Ríos-Motta

Departamento de Química, Universidad Nacional de Colombia, Bogotá, Colombia, A.A. 14490, Colombia

* Author to whom correspondence should be addressed.

Received: 26 April 2010; in revised form: 7 May 2010 / Accepted: 11 May 2010 / Published: 7 June 2010

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Abstract: A new series of N,N'-bis(2'-hydroxy-5'-substituted-benzyl)-N,N´-dimethylethane-1,2-diamines (N,N'-dimethyltetrahydrosalen) ligands were prepared in good yield by reduction of the respective 3,3'-ethylene-bis(3,4-dihydro-6-substituted-2H-1,3-benzoxazine) precursors with sodium borohydride . The ligands were characterized by IR, NMR, and elemental analysis, which showed the compounds to be consistent with the proposed structures. Ring-opening reactions of bis-1,3-benzoxazines in the presence of sodium borohydride to produce N,N’-dimethylated tetrahydrosalens (H₂ [H₂Me]salen) have not been reported in the literature.

Keywords: tetrahydrosalen; salan; bis-benzoxazines; tetradentate ligand

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MDPI and ACS Style

Rivera, A.; Rojas, J.J.; Salazar-Barrios, J.; Maldonado, M.; Ríos-Motta, J. Synthesis of a New Series of N,N’-Dimethyltetrahydrosalen (H₂ [H₂Me]salen) Ligands by the Reductive Ring-Opening of 3,3'-Ethylene-bis(3,4-dihydro-6-substituted-2H-1,3-benzoxazines). Molecules 2010, 15, 4102-4110.

AMA Style

Rivera A, Rojas JJ, Salazar-Barrios J, Maldonado M, Ríos-Motta J. Synthesis of a New Series of N,N’-Dimethyltetrahydrosalen (H₂ [H₂Me]salen) Ligands by the Reductive Ring-Opening of 3,3'-Ethylene-bis(3,4-dihydro-6-substituted-2H-1,3-benzoxazines). Molecules. 2010; 15(6):4102-4110.

Chicago/Turabian Style

Rivera, Augusto; Rojas, Jicli José; Salazar-Barrios, Jairo; Maldonado, Mauricio; Ríos-Motta, Jaime. 2010. "Synthesis of a New Series of N,N’-Dimethyltetrahydrosalen (H₂ [H₂Me]salen) Ligands by the Reductive Ring-Opening of 3,3'-Ethylene-bis(3,4-dihydro-6-substituted-2H-1,3-benzoxazines)." Molecules 15, no. 6: 4102-4110.

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