ChemInform Abstract: NEW SYNTHESIS OF 7‐BROMO‐1,3‐DIHYDRO‐3‐HYDROXY‐5‐(2′‐PYRIDYL)‐2H‐1,4‐BENZODIAZEPIN‐2‐ONE

KOVAC, T.; BELIN, B.; Fajdiga, T.; Šunjić, Vitomir

doi:10.1002/chin.198133253

Cited by 1 publication

(1 citation statement)

References 1 publication

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In our previous studies we investigated the use of metal complexes of C(3)‐substituted 5‐phenyl‐ and 5‐pyridyl‐1,4‐benzodiazepin‐2‐ones in noncatalytic, catalytic, and biocatalytic reactions 9−16. We have already reported on the oxidative C(3)‐acetoxylation of the 5‐pyridyl‐1,4‐benzodiazepine derivative to the 3‐acetoxy derivative promoted by a mixed reagent [Pb IV (AcO) 4 ]/I 2 17. In vitro metal‐catalysed C(3)‐oxygenation of 1,4‐benzodiazepin‐2‐ones has been unprecedented.…”

Section: Introductionmentioning

confidence: 99%

Copper(II)-Promoted Chemical Transformations of 3-Substituted 5-(2′-Pyridyl)-1,4-benzodiazepin-2-one Derivatives. Crystal Structures and Spectroscopic Characterisation of Metal Complexes

Višnjevac

Tušek-Božić

Majerić-Elenkov

et al. 2001

Eur. J. Inorg. Chem.

View full text Add to dashboard Cite

Enantiomerically pure 7‐bromo‐1,3‐dihydro‐3‐hydroxymethyl‐1‐methyl‐5‐(2′‐pyridyl)‐2H‐1,4‐benzodiazepin‐2one, (+)‐1, affords the dichloro adduct 3, [CuCl2(1)], when treated with a solution of CuCl2·2H2O in ethanol. Complex 3 is isolated as a racemic compound. The replacement of one chlorine atom with DMSO gives complex 4, [CuCl(1‐H)(DMSO)]. The C(3)‐oxygenated product appears as a racemic N,N,O‐tridentate ligand in the square‐pyramidal complex 5. Oxidative ring contraction of (+)‐1 yields 6‐bromo‐4‐ethoxy‐1,4‐dihydro‐1‐methyl‐4‐(2′‐pyridyl)‐1,3‐quinazoline, which acts as an N,N‐bidentate ligand in the tetrahedral complex 6. Reaction of 3‐acetoxymethyl‐7‐bromo‐1,3‐dihydro‐1‐methyl‐5‐(2′‐pyridyl)‐2H‐1,4‐benzodiazepin‐2‐one, (±)‐2, with CuCl2·2H2O, affords the square‐pyramidal complex 7, [CuCl2(2)]. In this complex the lactam oxygen atom of a neighbouring molecule binds to the fifth coordination site, hence forming an infinite chain of connected polyhedra in the crystal. Oxidative ring contraction of 2 leads to 6‐bromo1,4‐dihydro‐4‐hydroxy‐1‐methyl‐4‐(2′pyridyl)‐1,3‐quinazoline, which acts as an N,N‐bidentate ligand in the centrosymmetric binuclear five‐coordinate CuII complex 8. In this complex the di‐μ‐chloro bridges are asymmetrical: one Cl atom is in an apical position [Cu−Cl, 2.820 (7) Å], whereas the other is in an equatorial position [Cu−Cl, 2.252 (5) Å]. The complexes are characterised by IR spectroscopy and X‐ray structure analysis. Mechanisms of racemisation, oxygenation and ring contraction are discussed.

show abstract

Section: Introductionmentioning

confidence: 99%

Copper(II)-Promoted Chemical Transformations of 3-Substituted 5-(2′-Pyridyl)-1,4-benzodiazepin-2-one Derivatives. Crystal Structures and Spectroscopic Characterisation of Metal Complexes

Višnjevac

Tušek-Božić

Majerić-Elenkov

et al. 2001

Eur. J. Inorg. Chem.

View full text Add to dashboard Cite

show abstract

ChemInform Abstract: NEW SYNTHESIS OF 7‐BROMO‐1,3‐DIHYDRO‐3‐HYDROXY‐5‐(2′‐PYRIDYL)‐2H‐1,4‐BENZODIAZEPIN‐2‐ONE

Abstract: Die im Titel genannte Verbindung (IIc) wird aus Bromacetylamino‐benoylpyridin (Ia) hergestellt.

Cited by 1 publication

References 1 publication

Copper(II)-Promoted Chemical Transformations of 3-Substituted 5-(2′-Pyridyl)-1,4-benzodiazepin-2-one Derivatives. Crystal Structures and Spectroscopic Characterisation of Metal Complexes

Copper(II)-Promoted Chemical Transformations of 3-Substituted 5-(2′-Pyridyl)-1,4-benzodiazepin-2-one Derivatives. Crystal Structures and Spectroscopic Characterisation of Metal Complexes

Contact Info

Product

Resources

About