Acridinic acid

When the name ends in -insdure the translator may substitute -ic acid for this unless another acid already bears the resulting name thus Akridinsdure is often called acridic acid instead of the longer acridinic acid, but Mekonin-sdure should be translated meconinic acid because Mekonsdure has preempted the translation meconic acid. Such exceptions are given in the dictionary as far as possible, but in doubtful cases the longer form -inic acid would be the safer. 

Benzo ring cleavage of acridine results from oxidation with permanganate, the product being quinoline-2,3-dicarboxylic acid (acridinic acid), which is also the main product of ozonolysis in methanol (Scheme 26) (64JA38). 

Two examples of diene addition products have been claimed in the literature. Structures 141 and 142 were considered for a 1 1 adduct of anthranil and maleic anhydride, and since 3-phenylanthranil did not react analogously, structure 141 was preferred.271 Also, anthranil and jV-phenylmaleimide have been reported to give compound 143, which with alkali is hydrolyzed and dehydrated to give acridinic acid.272 Attempts to form Diels-Adler adducts between 3-benzoylanthranil and maleic anhydride or n-butyl vinyl ether met with no success.165... 

Reductive alkylation of N-methylacridinium (87) occurs when it is irradiated with carboxylic acid salts. The reaction is thought to proceed by electron transfer from the carboxylate to the excited acrldinium ring followed by decarboxylation of RCOO coupling of the alkyl radical produced with the acridinyl radical then gives (88). A very similar sequence probably occurs in a reaction proposed as a synthetic procedure for decarboxylation of carboxylic acids.In this case an aza-aromatic compound such as acridine is irradiated with a carboxylic acid in benzene in the presence of tert-butyl thiol. The authors propose that a hydrogen bonded acridine-acid complex is excited and that adiabatic proton transfer is followed by electron transfer. This produces RCOO which decarboxylates, and reduction of the alkyl radical then ensues. The major fate of the acridine is coupling to (89) if the reaction is perfonned in the absence of oxygen. 

Friedlander synthesis, 2, 445 Acridine-1,8-diones, hexahydro-synthesis, 2, 482 Acridine Orange colour and constitution, 1, 346 nucleic acid stain, 1, 179... 

A few studies on solvolyses by alcohols and by water are available. The hydrolyses studied include displacement of alkylamino groups from acridine antimalarials and of halogen from other systems. In all cases, these reactions appeared to be first-order in the heterocyclic substrate. By a detailed examination of the acid hydrolysis of 2-halogeno-5-nitropyridine, Reinheimer et al. have shown that the reaction rate varies as the fourth power of the activity of water, providing direct evidence that the only reactive nucleophile is neutral water, as expected. 

An acridine with a radically different substitution pattern, interestingly, still exhibits antimalarial activity. Condensation of acetone with diphenylamine in the presence of strong acid affords the partly reduced acridine, 20. Alkylation with 3-chloro-dimethylaminopropane (via the sodium salt of 20) affords dimethacrine (21). ... 

Dehydration of alcohol 36 with phosphorus pentoxide in refluxing xylene yields the 5H-diben7[(/,/]azepine 37.72 However, with concentrated hydrochloric acid, ring contraction to an acridine via a Wagncr-Mccrwcin rearrangement is preferred. 

The ring expansions of acridine derivatives to dibenz[/j, / ]azcpines (see Section 3.2.1.4.1.5.) are reversible in hot mineral acid.29 161-184 227 For example, 5-acetyl-52/-dibcnz[/j./]azcpine (1) in refluxing 48% hydrobromic acid furnishes 9-methylacridine (2).29... 

Nitroso-5//-dibenz[/j,/ azepine (see Section 3.2.1.5.4.1.) in methanolic hydrochloric acid undergoes rearrangement and ring contraction to a mixture of acridine (59%), acridine-9-carbaldehyde (trace), and 2-nitro-5//-dibenz[/ ,/ azepine (3% mp 176-178 C).184 However, in acetone and hydrochloric acid, the aldehyde (57 %) becomes the major product. On thermolysis, (or photolysis in the presence of oxygen), in hydroxylic solvents, the nitroso compound yields mainly acridine (36-76%) together with minor amounts of either 2-nitrodibenzazepine (4-6% by thermolysis) or acridine-9-carbaldehyde (18% by photolysis). However, in non-hydroxylic solvents, e.g. cumene, acridine-9-carbaldehyde (64%) is the major product. 

Halogenations of quinoline, isoquinoline, acridine, and phenanthridine will be discussed here. Reaction usually occurs in a homocyclic fused ring rather than in the 7r-deficient pyridine moiety, especially in acidic media. Relatively mild conditions suffice, but under more vigorous regimes radical involvement can result in heteroring halogenation. Substituents are able to modify reactivity and regiochemistry. 

The amino acid 58 was used in the solid-phase synthesis of sequence-specific DNA binding polyamides containing N-methylimidazole and N-methylpyrrole amino acids <96JACS6141> and it was also reported that the imidazole-acridine conjugate 59 could effectively catalyze the cleavage of t-RNA <96TL4417>. 

Bentin, T. and P.E. Nielsen. Superior duplex DNA strand invasion by acridine conjugated peptide nucleic acids. J. Am. Chem. Soc. 2003, 125, 6378-6379. 

Amino-3-nitrotoluene 1 b 415,419 Amino phases la 3 Aminophenazone lb312,314,354 2-Aminophenol lb 309, 310, 381 4-Aminophenol lb 309, 310, 381 Aminophenols lb 309,381,383,401 9-(p-Aminophenoxy)acridine lb 145 1-Aminopyrene la 61 4-Amino salicylic acid lb 309,310 Amino sugars lb 47,232-235,354 Aminotrimethylenephosphonic acid la 172... 

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