29184-58-5Relevant academic research and scientific papers
A concise Friedl?nder/Buchwald-Hartwig approach to the total synthesis of quindoline, a bioactive natural indoloquinoline alkaloid, and toward the unnatural 10-methylquindoline
Méndez, María V.,Simonetti, Sebastian O.,Kaufman, Teodoro S.,Bracca, Andrea B. J.
, p. 10803 - 10813 (2019/07/15)
A new approach toward the synthesis of quindoline, a recognized indoloquinoline alkaloid, is reported. The sequence comprises the synthesis of 2-(2-nitrophenyl)quinoline through an optimized Friedl?nder condensation of 2-amino benzaldehyde with 2-nitroacetophenone, followed by the selective C-3 bromination of the quinoline moiety to direct the cyclization, reduction of the nitro group and a final Buchwald-Hartwig cyclization. In addition, quindoline was also converted to the unnatural 10-methylquindoline by reaction with dimethyl carbonate under DBU promotion. It was found that the non-directed reductive cyclization of 2-(2-nitrophenyl)quinoline results in indazolo[2,3-a]quinoline, instead of yielding quindoline. DFT calculations were employed to explain this reaction outcome; this finding suggested that the result of a previously reported total synthesis of quindoline should be revised.
Mapping the reactivity of the quinoline ring-system – Synthesis of the tetracyclic ring-system of isocryptolepine and regioisomers
H?heim, Katja S.,Urdal Helgeland, Ida T.,Lindb?ck, Emil,Sydnes, Magne O.
, p. 2949 - 2957 (2019/04/25)
Bromoquinolines (2-bromoquinoline – 8-bromoquinoline and 5-bromo-3-methoxyquinoline) and 2-aminophenylboronic acid hydrochloride were subjected to Suzuki-Miyaura cross-coupling conditions resulting in formation of the desired biaryl systems in good yields. The resulting biaryls were then subjected to palladium catalyzed C–H activation/C–N bond formation utilizing PdCl2(dppf). The reactions revealed large differences in reactivity depending on the attachment point for the 2-aminophenyl group on the quinoline. The variation in the reactivity was rationalized based on the electron distribution around the quinoline ring-system.
A Novel Route to 2-Arylquinolines: Reductive Cleavage of 2′-Nitroaryl-Δ2 -isoxazolines
Kamath, Prashantha,Viner, Russell C.,Smith, Stephen C.,Lal, Mukul
supporting information, p. 1341 - 1345 (2017/06/27)
A novel synthetic route for the synthesis of quinolines starting from Δ 2 -isoxazolines under reductive conditions is reported. The reductive cyclization to quinolines is achieved under both metal and metal-free conditions. The reaction proceeds via an intramolecular N-H?O hydrogen bond intermediate, accelerating the reductive cleavage 1000-fold (DFT calculations) in comparison with non-hydrogen bonded system.
Rhodium-Catalyzed N-tert-Butoxycarbonyl (Boc) Amination by Directed C H Bond Activation
Wippich, Julian,Truchan, Nadina,Bach, Thorsten
supporting information, p. 2083 - 2087 (2016/07/16)
N-tert-Butoxycarbonyl azide (BocN3) was shown to be an efficient and economic source for the directed introduction of N-Boc protected amino groups into the thiophene and benzene nucleus. Yields for the amination of 2-pyridin-2-ylthiophenes (10 examples) were 52–88%. For the amination of the respective benzenes (10 examples) yields between 54% and 99% were recorded with an improved reactivity observed for substrates that bear an electron-withdrawing group. The reaction was applied to short total syntheses of the indoloquinoline alkaloids quindoline and cryptolepine. The facile removal of the Boc protecting group was the key to the success of the syntheses. The scope of the reaction was extended to a C(sp3) H bond amination and to the amination of 2-phenyloxazoline. For the amination of 2-pyridin-2-ylbenzene a kinetic deuterium isotope effect of 2.0 was determined. (Figure presented.) .
Investigating chelating sulfonamides and their use in metalloproteinase inhibitors
Tanakit, Alisa,Rouffet, Matthieu,Martin, David P.,Cohen, Seth M.
, p. 6507 - 6515 (2012/09/21)
Matrix metalloproteinase inhibitors (MMPi) utilize zinc-binding groups (ZBGs) to chelate the catalytic Zn(ii) ion resulting in enzyme inhibition. Adapting findings from the literature of Zn(ii) ion sensors, we previously reported chelating sulfonamide inh
An alternative synthesis of quindoline and one of its closely related derivatives
Csanyi,Timari,Hajos
, p. 3959 - 3969 (2007/10/03)
The alkaloid Quindoline (13) and one of its tetracyclic isomer indazolo[2,3-a]quinoline (8) have been synthesised utilising the Pd(0)- catalysed cross-coupling reaction of pivaloylamino phenylboronic acid (2) with substituted quinolines.
Synthesis of Indazoloquinolines
Reddy, Y. Padma,Reddy, K. Kondal
, p. 563 - 564 (2007/10/02)
A number of 2-(o-nitrophenyl)quinolines (Ia-e) have been synthesised and converted via amines (IIa-e) into corresponding azides (IIIa-e).Thermolysis and deoxygenation of 2-(o-azidophenyl)-(IIIa-e) and 2-(o-nitrophenyl)-(Ia-e)-quinolines respectively lead
