Synthesis of 1,4-benzodiazepin-3-ones and 1,5-benzodiazocin-4-ones by addition of Grignard reagents to derivatives of o-aminobenzonitrile

2009 ◽  
Vol 7 (6) ◽  
pp. 1184 ◽  
Author(s):  
Birgitta Pettersson ◽  
Anna Rydbeck ◽  
Jan Bergman
2014 ◽  
Vol 4 (7) ◽  
pp. 1997-2005 ◽  
Author(s):  
R. Oost ◽  
J. Rong ◽  
A. J. Minnaard ◽  
S. R. Harutyunyan

New derivatives of copper complexes of Josiphos family ligands have been prepared and studied in asymmetric catalytic addition of Grignard reagents to enones, enoates and aromatic ketones.


1997 ◽  
Vol 52 (9) ◽  
pp. 1037-1042 ◽  
Author(s):  
Max Herberhold ◽  
Thomas Hofmann ◽  
Stefanie Weinberger ◽  
Bernd Wrackmeyer

Mixed manganese sandwich complexes containing a silyl-substituted cyclopentadienyl ring, e. g. (η5 - C5H4 - R)Mn(η6- C6H6) (3a - c) and (η5- C5H4 - R)Mn(η6- C6H5 - Ph) (4a - c); (R = SiMe3 (a), Si2Me5 (b) and SiMe2tBu (c)), were obtained in low yield via intermediates {(η5 - C5H4 - R)MnCl} and their reaction with phenyl Grignard reagents. Use of the 4-trimethylsilyl-phenyl magnesium halide in the reaction with the intermediate {CpMnCl} led to complexes with silylsubstituted arene rings, CpMn(η6 - C6H5 - R′) (5a) and CpMn(η6 -R′ - C6H5 - C6H5 - R′) (6a); (R′ = SiMe3 (a)). Dilithiation of CpMn6H6) (1) and subsequent reaction with a chlorosilane gave (η5-C5H4 - R)Mn(η6 - C6H5 - R′) (7a,b); (R = R′ = SiMe3 (a), Si2Me5 (b)). A cyclophane 8 in which five- and six-membered ring are linked through a -Me2Si-SiMe2- bridge was obtained using 1,2-dichloro-tetramethyldisilane. The mixed manganese sandw ich complexes were thoroughly characterized by 1H , 13C, 29Si and 55Mn NMR spectroscopy. The 55Mn spectra can be used to detect low-yield side-products.


1967 ◽  
Vol 45 (15) ◽  
pp. 1761-1765 ◽  
Author(s):  
P. Canonne ◽  
L. C. Leitch

Several new β-hydroxyketones having the formula CH3R′C(OH)CH2COCH3 have been prepared by the action of Grignard reagents on 2,4-pentanedione. With benzyl-, o-xylyl-, p-xylyl-, 3,4-dimethylbenzyl-, 2,5-dimethylbenzyl-, 3,5-dimethylbenzyl-, and α-naphthylmethyl-magnesium chlorides, 60 to 75% yields of the β-hydroxyketones were obtained. Phenyl-, p-tolyl-, and p-trifluoromethylphenyl-magnesium bromide and 2,4-dimethylbenzylmagnesium chloride gave lower yields, whereas with α-naphthylmagnesium bromide no β-hydroxyketone was formed. The β-hydroxyketones were separated from non-ketonic by-products by means of Girard's reagent T or P. Solid derivatives of the β-hydroxyketones could not be prepared.


2020 ◽  
Vol 44 (25) ◽  
pp. 10199-10202
Author(s):  
Akim V. Shmalko ◽  
Sergei A. Anufriev ◽  
Marina Yu. Stogniy ◽  
Kyrill Yu. Suponitsky ◽  
Igor B. Sivaev

A series of B-substituted arylazo derivatives of ortho-carborane 3-XC6H4-NN-1,2-C2B10H11 (X = p-NMe2, p-OMe, o-Me) were synthesized by reaction of its diazonium derivative [3-N2-o-C2B10H11][BF4] with the corresponding Grignard reagents.


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