22292-39-3

Upstream product

• 10328-92-4 N-Methylisatoic anhydride 
• 85-91-6 Methyl N-methylanthranilate 
• 54083-72-6 methyl N-methyl-N-(o-aminobenzoyl)anthranilate 
• 74-88-4 methyl iodide 

Relevant academic research and scientific papers

Successive formation of two amide linkages between two benzene rings

To successively construct two amide bonds between two benzene rings, the reaction of methyl N-alkylanthranilate and N-alkylisatoic anhydride in the presence of a base was studied. When the reaction was carried out with lithium hexamethyldisilazide and N,N,N,N-tetramethylethylenediamine in THF at 70 °C under reduced pressure, a cyclic diamide was obtained in high yield.

Conformational Behaviour of Medium-sized Rings. Part 11. Dianthranilides and Trianthranilides

Two approaches to the stepwise syntheses of N,N'-di- and N,N',N''-tri-substituted trianthranilide derivatives (5)-(20) are described.In the shorter synthetic route, the key acyclic intermediate, N-anthranilic acid (26) is prepared in a stepwise manner from anthranilic acid, isatoic anhydride (23), followed by o-nitrobenzoyl chloride.Alkylations of the amide functions at nitrogen, reductions of the aromatic nitrogroups, and cyclisations of the acyclic amino-acid derivatives provide a direct route to N,N'-dimethyl- (5) and N,N'-dibenzyl- (14) trianthranilides.Further alkylations or acylations of either (5) or (14) afford (i) N,N',N''-trimethyltrianthranilide (7) and its trideuteriomethyl analogue (8), (ii) N,N'-dimethyl-N''-acetyl- (10), -N''-benzoyl- (11), and -N''-benzyl- (12) trianthranilides, (iii) N,N',N''-tribenzyltrianthranilide (15), and (iv) N,N'-dibenzyl-N''-methyltrianthranilide (16).In the longer synthetic route, the key acyclic intermediate, methyl N-methyl-N-anthranilate (42) is prepared in a stepwise manner from anthranilic acid and two molar equivalents of o-nitrobenzoyl chloride.Alkylations of the unsubstituted amide functions at nitrogen, reductions of the aromatic nitro-groups, and cyclisations of the acyclic amino-acid derivatives provide, not only an alternative route to N,N'-dimethyltrianthranilide (5) but also, a general route to the N-methyl-N'-trideuteriomethyl- (6), N-methyl-N'-benzyl- (17), and N-methyl-N'-ethyl- (19) analogues.Further alkylations of these N,N'-disubstituted derivatives afford N-methyl-N',N''-di(trideuteriomethyl)- (9), N-methyl-N'-trideuteriomethyl-N''-benzyl- (13), N-methyl-N'-benzyl-N''-ethyl- (18), and N-methyl-N'-ethyl-N''-benzyl- (20) trianthranilides.The constitutionally symmetrical N,N',N''-trimethyl- (7) and N,N',N''-tribenzyl- (15) trianthranilides exist in solution as an equilibrium mixture of propeller and helical conformations.In the case of the N,N',N''-trimethyl derivative (7), the predominant diastereoisomer with the helical conformation has been isolated as a pure compound.In the case of the N,N',N''-tribenzyl derivative (15), the propeller and helical conformational diastereoisomers have both been characterised as crystalline compounds.For both these compounds, the free-energy barriers to conformational inversion and interconversion processes in solution have been obtained from (i) direct equilibration experiments and (ii) dynamic 1H n.m.r. spectroscopy.Constitutionally unsymmetrical N,N'-di- and N,N',N''-tri-substituted trianthranilide derivatives can adopt three helical conformations in addition to a propeller conformation.Assignments have been made to conformations and conformational diastereoisomers of the N,N'-dimethyl- (5), N,N'-dimethyl-N''-benzyl- (12), N,N'-dibenzyl- (14), N,N'-dibenzyl-N''-methyl- (16), N-methyl-N'-benzyl- (17), N-methyl-N'-benzyl-N''-ethyl- ...