250591-69-6Relevant articles and documents
C–H Arylation of N-Heteroarenes under Metal-Free Conditions and its Application towards the Synthesis of Pentabromo- and Pentachloropseudilins
Kumar, Mukesh,Sharma, Shweta,Sil, Parijat,Kushwaha, Manoj,Mayor, Satyajit,Vishwakarma, Ram A.,Singh, Parvinder Pal
supporting information, p. 3591 - 3598 (2019/06/20)
Herein, we are reporting metal-free conditions for radical initiation and direct C–H arylation of N-heteroarenes. Starting from aniline, the corresponding arenediazonium salt generated in situ is reduced to an aryl radical in the presence of chloropromazine hydrochloride, a new reagent for this application. The optimized procedures are mild, operationally simple, and are working successfully with more diverse substrates in comparison to reported methods. The optimized method is also employed for the synthesis of marine natural products Pentabromo- and Pentachloropseudilins (PBP/PCP). In the present study, we also validated the potential of the Pentachloropseudilin (PCP), thus synthesized, for inhibition of Myosin1 function in mammalian cells and confirmed that PCP phenocopies Myosin1c depletion in cells.
Optimization of the Suzuki coupling reaction in the synthesis of 2-[(2-substituted)phenyl]pyrrole derivatives
Aleskovic, Marija,Basaric, Nikola,Mlinaric-Majerski, Kata
experimental part, p. 1329 - 1335 (2012/01/04)
A facile three-step synthesis of 2-(2-aminophenyl)pyrrole (1) and 2-[(2-aminomethyl)phenyl]pyrrole (2) is reported by use of Suzuki coupling of N-Boc-pyrrol-2-yl boronic acid (3) and o-substituted aryl halogenides, followed by hydrogenation. The Pd-catalyzed cross-coupling reaction is optimized to be applicable to a wide range of substitued aryl halogenides, with electron-donating and electron-withdrawing substituents, 5a-g. Moreover, Pd-catalyzed coupling of o-bromoaniline and 3 could be applied for the one-step preparation of pyrrolo[1,2-c]quinazolin-5(6H)-one (8). Copyright
3,5-diaryl-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) dyes: Synthesis, spectroscopic, electrochemical, and structural properties
Burghart, Armin,Kim, Heejin,Welch, Mike B.,Thoresen, Lars H.,Reibenspies, Joe,Burgess, Kevin,Bergstroem, Fredrik,Johansson, Lennart B.-A.
, p. 7813 - 7819 (2007/10/03)
This research was undertaken to obtain new 'BODIPY' dyes that fluoresce at relatively long wavelengths. The title compounds 1a-e were prepared via a divergent route involving Suzuki couplings of arylboronic acids to N-tert- butoxycarbonyl-4-bromopyrrole 2, condensation of the products with an acid chloride, and incorporation of the boron difluoride entity. Two alkyl- substituted systems 7a and 7b were also prepared for comparison; the critical difference between structures 1 and 7 is that the former have an aryl group attached to each pyrrole nucleus whereas the latter only have alkyl substituents on that same ring. UV absorption and fluorescence emission data were compared for compounds 1 and 7. Absorption and fluorescence emission maxima for compounds 1 occur at higher wavelengths than for compounds 7, and the Stokes shifts for the aryl-substituted compounds 1 are larger than for the alkyl-substituted compounds 7. Fluorescence quantum yields measured for compounds 1 are less than for compounds 7, and possible reasons for this are outlined. Other physical data for the compounds were also collected. Oxidation and reduction potentials of the systems were obtained from cyclic voltammetry experiments, and a single-crystal X-ray structure determination was performed for the bisnaphthyl-substituted compound 1b.
