ChemInform Abstract: ZUR DARSTELLUNG EINIGER N‐ARYLIERTER 5‐METHOXYANTHRANILSAEUREN

Hannig, E

doi:10.1002/chin.197537185

Cited by 2 publications

(2 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The analytical data were in accord with literature values. 9 A suspension of 2,3-dimethoxy-10-methylacridin-9(10H)one (1 g, 3.70 mmol) was heated under reflux in HBr (48%, 20 mL) for 20 h. The solvent was removed in vacuo and the resulting solid was crystallized from MeOH to give pure 9.…”

Section: 3-dihydroxy-10-methylacridin-9(10h)-one (9)mentioning

confidence: 99%

Photoswitchable Macrocycles Incorporating Acridane Moieties

Orda-Zgadzaj¹,

Abraham²

2007

Synthesis

View full text Add to dashboard Cite

show abstract

Section: 3-dihydroxy-10-methylacridin-9(10h)-one (9)mentioning

confidence: 99%

Photoswitchable Macrocycles Incorporating Acridane Moieties

Orda-Zgadzaj¹,

Abraham²

2007

Synthesis

View full text Add to dashboard Cite

show abstract

“…Compound 3a was obtained by a modified procedure of Krishnegowda using EtOH as solvant and 2-bromobenzoïc acid [7]; while use of dimethoxyethane instead of 1-pentanol under reflux yielded 3b [8] The cyclization of 3a,b could be performed by FriedelCrafts acylation in polyphosphoric acid or in sulfuric acid but the best yields were obtained in polyphosphoric acid after purification leading to 2-methoxy-9(10H)-acridinone (4a) and 2-methoxy-7-methyl -9(10H)-acridinone (4b) in 65 % and 95 % yield respectively. Demethylation was also observed performing the cyclization of anthranilic acid (3b) in sulfuric acid; leading to the hydroxy derivative 2-hydroxy-7-methyl-acridin-9(10H)-one (5) in 89 % yield (Scheme 2).…”

mentioning

confidence: 99%

Oxidative coupling of acridinones: Synthesis of new C₂‐symmetry atropisomers

Scarpellini‐Charras¹,

Boyer²,

Filloux³

et al. 2008

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

The preparation of symmetric 2,2'-dimethoxy-10,10'-biacridinyl-9,9'-dione atropisomers were obtained by the oxidative coupling of 9(10H)-acridinone with 1,3-dibromo-5,5-dimethyl-imidazolidine-2,4-dione J. Heterocyclic Chem., 45, 67 (2008).Acridine derivatives are well known therapeutic agents due to their wide range of pharmacological and biological activities [1], and many C 2 -symmetry derivatives have been reported in the literature [2]. We reported previously the prep artion of symmetrical heterocyclic host compounds related to bianthryl [3] using unsubstituted 9,9-biacridinyl [4]; but no inclusion compounds were observed with these derivatives. On the other hand 2,2'-dimethoxy-9,9'-biacridines atropisomers proved useful in molecular recognition showing a 'scissor-like' host conformation and guest inclusion of chloroform in their crystalline structure [5]. Recently we obtained the first chiral (aR)-(-)-9,9'-biacridinyl-2,2'-diol atropisomer enantiomerically pure by derivatization and recrystallisation [6]. Hence we were interested in the preparation of new C 2 symmetry derivatives bridged at positions 10,10' and report now the synthesis of 2,2'-dimethoxy-10,10'-biacridinyl-9,9'-diones using the corresponding methoxy-9(10H)-acridinones 4a and 4b.Our approach towards this synthesis was based on the preparation of the 2-methoxy-and 2-methoxy-7-methyl-9(10H)-acridinones (4a) and (4b) followed by oxidative coupling to yield the desired acridinone dimers.First, 4'-methoxyphenyl-N-anthranilic acid (3a) and 5-methoxy-4'-methyl-N-phenylanthranilic acid (3b) were prepared by Ullmann's reaction between 2-bromo-benzoic acid and 4-alkylanilines (2a) and (2b). Compound 3a was obtained by a modified procedure of Krishnegowda using EtOH as solvant and 2-bromobenzoïc acid [7]; while use of dimethoxyethane instead of 1-pentanol under reflux yielded 3b [8] (Scheme 1). The cyclization of 3a,b could be performed by FriedelCrafts acylation in polyphosphoric acid or in sulfuric acid but the best yields were obtained in polyphosphoric acid after purification leading to 2-methoxy-9(10H)-acridinone (4a) and 2-methoxy-7-methyl -9(10H)-acridinone (4b) in 65 % and 95 % yield respectively. Demethylation was also observed performing the cyclization of anthranilic acid (3b) in sulfuric acid; leading to the hydroxy derivative 2-hydroxy-7-methyl-acridin-9(10H)-one (5) in 89 % yield (Scheme 2). Then, we tried the oxidative homocoupling of 2-methoxy-9(10H)-acridinone (4a) and 2-methoxy-7-methyl-9(10H)-acridinone (4b), according to Graebe's procedure with sodium bichromate in acetic acid [9] successfully used in the laboratory for the preparation of 10,10'-biacridinyl-9,9'-dione derivatives, [4] and also with tris(acetyl-acetonato)cobalt(III), in deuteriodimethyl-

show abstract

ChemInform Abstract: ZUR DARSTELLUNG EINIGER N‐ARYLIERTER 5‐METHOXYANTHRANILSAEUREN

Cited by 2 publications

References 0 publications

Photoswitchable Macrocycles Incorporating Acridane Moieties

Photoswitchable Macrocycles Incorporating Acridane Moieties

Oxidative coupling of acridinones: Synthesis of new C₂‐symmetry atropisomers

Contact Info

Product

Resources

About

ChemInform Abstract: ZUR DARSTELLUNG EINIGER N‐ARYLIERTER 5‐METHOXYANTHRANILSAEUREN

Cited by 2 publications

References 0 publications

Photoswitchable Macrocycles Incorporating Acridane Moieties

Photoswitchable Macrocycles Incorporating Acridane Moieties

Oxidative coupling of acridinones: Synthesis of new C2‐symmetry atropisomers

Contact Info

Product

Resources

About

Oxidative coupling of acridinones: Synthesis of new C₂‐symmetry atropisomers