13082-10-5Relevant academic research and scientific papers
Alkaloids, limonoids and furocoumarins from three Mexican Esenbeckia species
Dreyer, David L.
, p. 941 - 944 (1980)
The chemical constituents of three Mexican Esenbeckia species have been determined. Rutaevin was the main limonoid present in the seeds of all three species, E. litoralis, E. flava and E. berlandieri. The husks, leaves, wood and bark contained a wide array of known furocoumarins and furoquinoline alkaloids. In addition, 1-hydroxy-3-methoxy-N-methylacridone was obtained from E. litoralis bark and a new natural 2-quinolone alkaloid, formulated as 3,3-diisopropyl-N-methyl-2,4-quinoldione, was obtained from E. flava wood. The structure was assigned from spectroscopic considerations and conversion to N-methylhaplofoline.
Weakly Coordinating, Ketone-Directed (η5-Pentamethylcyclopentadienyl)cobalt(III)- and (η5-Pentamethylcyclopentadienyl)rhodium(III)-Catalyzed C?H Amidation of Arenes: A Route to Acridone Alkaloids
Bera, Sourav Sekhar,Sk, Md Raja,Maji, Modhu Sudan
supporting information, p. 1806 - 1811 (2019/01/14)
The weakly coordinating, ketone-directed, regioselective monoamidation of aromatic ketones, chalcone, carbazole, and benzophenones was achieved by employing high-valent cobalt and rhodium catalysis to access numerous biologically important molecular building blocks. This amidation proceeded smoothly with a variety of ketones and several amidating partners. The application of the products in the synthesis of various heterocycles, including acridones, indoles, quinoline, quinolones, quinolinones, and quinazolines, was also explored. The total synthesis of acridone-based alkaloids, namely, toddaliopsin A, toddaliopsin D, and arborinine, and the formal synthesis of acronycine and noracronycin were also accomplished by applying this method. A mechanistic study revealed this amidation reaction follows a base-assisted intermolecular electrophilic substitution pathway.
Synthesis of o -(dimethylamino)aryl ketones, acridones, acridinium salts, and 1 H -indazoles by the reaction of hydrazones and arynes
Dubrovskiy, Anton V.,Larock, Richard C.
, p. 11232 - 11256 (2013/02/23)
A novel, efficient route to biologically and pharmaceutically important o-(dimethylamino)aryl ketones, acridones, acridinium salts, and 1H-indazoles has been developed starting from readily available hydrazones of aldehydes and o-(trimethylsilyl)aryl triflates. The reaction proceeds through arynes under mild conditions, tolerates a wide range of functional groups, and provides the final products in good to excellent yields.
Carbanionic friedel-crafts equivalents. Regioselective directed Ortho and remote metalation-C-N cross coupling routes to acridones and dibenzo[b,f]azepinones
MacNeil, Stephen L.,Gray, Matthew,Gusev, Dmitry G.,Briggs, Laura E.,Snieckus, Victor
supporting information; experimental part, p. 9710 - 9719 (2009/04/07)
(Chemical Equation Presented) Carbanion-mediated general regioselective routes to acridones 4 (Table 2) and dibenzo[b,f]azepinones 20 (Table 4) are described. Buchwald-Hartwig C-N cross coupling of o-halo benzamides 1 with anilines 2 or 16, followed by simple N-methylation, dependably provides N-methyl diarylamines 3 (Table 1) and 18 (Table 3). Upon treatment with LDA, 3 and 18 are converted into acridones 4 and dibenzo[b,f]azepinones 20, respectively, in good to excellent yields with regioselectivity which depends upon the presence or absence of directed metalation groups (DMGs). Brief investigations as follows are described: the synthesis of desmethyl acridone 15 (Scheme 4), an attempt to effect a double-directed remote metalation sequence which leads only to a monocyclization product 13 (Scheme 3), and an analogous but nonregioselective route to a xanthone 22 and dibenzo[b,f]oxepinone 24 (Scheme 5). DFT calculations reveal low energy conformations for compounds 18b and 23 which account for product formation and indicate that the cyclization reactions are under kinetic control.
Directed ortho and remote Metalation - Cross coupling connections. Buchwald-Hartwig synthesis of 2-carbamoyl diarylamines. Regioselective anionic routes to acridones, oxindoles, dibenzo-[b,f]azepinones, and anthranilate esters
MacNeil, Stephen L.,Gray, Matthew,Briggs, Laura E.,Li, Jim J.,Snieckus
, p. 419 - 421 (2007/10/03)
2-Carboxamido diarylamines 1f, 7, and 9, efficiently available by Buchwald-Hartwig C-N cross coupling reactions, serve as starting materials for new anionic routes to acridones 2d, oxindoles 10, dibenzo[b, f]azepinones 11, and anthranilate esters 8.
Reaction of Noracronycine and 1-Hydroxy-3-methoxy-10-methylacridone with Alkyl- and Aryl-lithiums: Formation of Quinone Methides
Jolivet, Catherine,Rivalle, Christian,Bisagni, Emile
, p. 511 - 516 (2007/10/02)
Alkyl- and aryl-lithiums reacted with noracronycine and 1-hydroxy-3-methoxy-10-methylacridone in a one-step addition-dehydration transformation to provide the corresponding 7- and 9-substituted derivatives having a quinone methide function and, therefore,
A Short Efficient Route to Acronycine and Other Acridones
Horne, Stephen,Rodrigo, Russell
, p. 1046 - 1048 (2007/10/02)
A Fries type rearrangement of N-tosyl-o-iodobenzanilides, triggered by lithium-iodine exchange at low temperature is the key step in a general, regiospecific synthesis of acridones.
Natural Product Chemistry, 143 Convenient Synthesis of Isoacronycine and Some Other New Acridone Derivatives
Reisch, Johannes,Herath, H. M. T. Bandara,Kumar, N. Savitri
, p. 685 - 690 (2007/10/02)
The iodination of 1,3-dihydroxy-9-acridone (1), 1-hydroxy-3-methoxy-10-methyl-9-acridone (2) and 1,3-dihydroxy-10-methyl-9-acridone (3) yields 1,3-dihydroxy-2,4-diiodo-9-acridone (4), 1-hydroxy-2-iodo-3-methoxy-10-methyl-9-acridone (5) and 1,3-dihydroxy-2-iodo-10-methyl-9-acridone (6), respectively.The methylation of 4 and 5 gives 2,4-diiodo-1,3-dimethoxy-10-methyl-9-acridone (7) and 2-iodo-1,3-dimethoxy-10-methyl-9-acridone (9), respectively.The direct C-C coupling of 2-methyl-3-buten-2-ol to the compounds 5, 7 and 9 by palladium catalysed Heck condensation method gives three new acridone derivatives 1-hydroxy-2-(3-hydroxy-3-methyl-1-butenyl)-3-methoxy-10-methyl-9-acridone (10), 2,4-bis(3-hydroxy-3-methyl-1-butenyl)-1,3-dimethoxy-10-methyl-9-acridone (12) and 2-(3-hydroxy-3-methyl-1-butenyl)-1,3-dimethoxy-10-methyl-9-acridone (13) while compound 6 is converted into isonoracronycine (11).The methylation of 11 yields isoacronycine (14). Key words: Acridone alkaloids / Heck condensation / Isonoracronycine / Isoacronycine
ACRIDONES FROM THE REACTION OF N-LITHIO ANTHRANILATES WITH BENZYNES. A SHORT SYNTHESIS OF ACRONYCINE
Watanabe, Mitsuaki,Kurosaki, Akio,Furukawa, Sunao
, p. 1264 - 1267 (2007/10/02)
The lithium salt of methyl N-methylanthranilate reacted with the benzyne derived in situ from aryl halides to give a N-methylacridone derivatives in a one-pot process.Using this method, a short synthesis of acronycine has been achieved.KEYWORDS - acridone; acronycine; benzyne; lithium N-isopropylcyclohexylamide; N-lithio anthranilate
