Anthranilic derivatives

S-Formylbenzofuroxan has been prepared, but the 4-acetyl compound rearranges under the conditions used for its jDreparation, to an anthranil derivative (see Section VIII). 

Marcus, S.L., and Balbinder, E. (1972) Use of affinity matrices in determining steric requirements for substrate binding Binding of anthranilate 5-phosphoribosyl-pyrophosphate phosphoribosyltransferase from Salmonella typhimurium to Sepharose-anthranilate derivatives. Anal. Biochem. 48, 448-459. 

Scheme 70 Cathodic reduction of nitrocarhonyl compounds to anthranilic derivatives. Ph...

Benzodiazepinediones 15 have been synthesized starting from anthranilic derivatives 13 and Armstrong convertible isocyanides 1. When the amino group of 13 is secondary, it does not interfere too much with the Ugi reaction, and the acid... 

Nitrogen-containing compounds-. Anthranilate derivatives, such as avenanthramides, and avenalmin I, II, and III have been reported in A. sativa (Gramineae) (Figure 26).261 262... 

Under similar reaction conditions, methyl anthranilate derivative 9 reacts with ammonia to produce 7-amino-6-nitroquinazoline-2,4(l//,3//)-dione. ... 

Aminoisoxazoles were obtained from (Z)-3-alkyl-3-nitro-2-phenylpropenenitriles using baker s yeast <1996SL695>. Reductive cyclizations of 2-nitroacylarenes allowed the synthesis of anthranil derivatives. For example, a series of 5-substituted 2,1-benzisoxazoles where prepared by reduction with SnCl, and subsequent... 

Roblot, F., Hocquemiller, R., Cave, A. Obtention of anthranil derivatives by a modified Bischler-Napieralski reaction. J. Chem. Res., Synop. 1989, 344-345. 

The synthesis of several other plant metabolites, such as auxin, indole glucosinolates, anthranilate-derived alkaloids, and tryptamine derivatives, could depend on indole as an intermediate. Indole is also found in the scent of flowers such as lilac and robinia. Therefore, it is possible that the recruitment of an indole-3-glycerol phosphate lyase function from TSA genes might have occurred independently several times during plant evolution. 

In addition to the relatively simple anthranilic-derived metabolites mentioned above, several distinctive types of alkaloids are derived from this amino acid. Most of these are associated with the Rutaceae and related families of the Rutales. Among these groups of alkaloids are the quinazoline, pyrroloquinazoline, quinazolinocarboline, quinoline, furoquinoline, and acridone types. 

Alkaloids of the 1-benzyltetrahydroisoquinoline type are assumed to be primitive in the Rutaceae and the plants producing them belong to the most primitive extant genera of the family. As anthranilate-derived alkaloids are found in some of the same genera, it appears that the evolutionary trend was for direct replacement of one type with another (Waterman and Khalid, 1981). The taxa that do not have 1-benzyltetrahydroquinoline alkaloids [e.g., tribes Diosmeae and Boronieae (Rutoideae) and the subfamily Aurantioideae], appear to be relatively advanced. 

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