Reaction of quimoxalines with β,γ-unsaturated grignard reagents

1,2,3,4-Tetrahydroquinoxaline

“…Compound I crystallizes in the orthorhombic space group Pbca. The structure of I exhibits bond distances and angles that are unexceptional and are comparable to those of the relatively few previously reported tetrahydroquinoxaline structures (Ammon et al, 1979;Pniewska & Anulewicz, 1986;Epifani et al, 1987;Beddos et al, 1992;Brown et al, 1995;Nair et al, 2004).…”

“…For related literature, see: Ammon et al (1979); Beddoes et al (1992); Bohlmann (1952); Brown et al (1995); Bugle & Osteryoung (1979); Deprez-Poulain & Melnyk (2005); Eary & Clausen (2006); Epifani et al (1987); Graham et al (2000); Hamer & Holliday (1963); Maeyer et al (2003); Maurer et al (2004); McKinney et al (2005); Murata et al (1987); Nair et al (2004); Nose & Kudo (1984); Pike et al (2002); Pniewska & Anulewicz (1986); Ranu et al (1998); Wiles & Pike (2006).…”

Allylmagnesium Bromide

“…54 Mono and bis addition reactions of the allylic Grignard reagents to the C=N bond of quinoxalines afford high yields of allyldihydroquinoxalines and diallyltetrahydroquinoxalines; dehydrogenation with 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone leads to monoallyl-and diallylquinoxalines. 55 Similarly, reaction with pyrimidines furnishes excellent yields of allylpyrimidines. 56 Reactions with Nitro Compounds and Nitriles.…”

Nucleophilic Substitution on 2-Monosubstituted Quinoxalines Giving 2,3-Disubstituted Quinoxalines: Investigating the Effect of the 2-Substituent

“…Substitution of hydrogen by C -nucleophiles on electron deficient arenes has been reported extensively [17,18,19]. The reaction of quinoxaline derivatives with aryl and alkyl nucleophiles has been investigated [20,21,22,23,24,25,26]. C -nucleophiles have been shown to add to 6-aminoquinoxaline [9,20] affording alkyl- and aryl-substituted quinoxalines in low to high yields.…”