Abstract
Ethyl 2-[2-(4-nitrobenzoyl)-1H-indol-3-yl]acetate was prepared in good yield and characterized by the aza-alkylation/intramolecular Michael cascade reaction of (E)-ethyl 3-[2-(tosylamino)phenyl]acrylate with 2-bromo-4′′-nitroacetophenone, followed by desulfonative dehydrogenation with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) The structure of the newly synthesized compound was determined using 1H-,13C-NMR, IR and mass spectral data.
Highlights
Tathae astrreucitnuraecocfocrodmapnocuenwd i4thwaths ecoansfisrummededbys1tHru- cantudr1e3C. -NMR, IR, mass spectral data, and all data are in accordance with the assumed structure
All reagents were used as received without further purification
Developed chromatograms werevisualized by fluorescence quenching and anisaldehyde stain. 1H- and 13C-NMR spectra were recorded on a 400 MHz instrument (Bruker BioSpin GmbH, Karlsruhe, Germany) as noted, and are internally referenced to residual protio solvent signals
Summary
PharmaceutIincdaolslesoarreuwnedll erstgaobilinshgedclaisnpicriavliletgreiadlssca[f4fo].lds,Acommomnognlythenecoinundtoerleeds,in2m-aarnoyyblioilnogdiocallely-3-acetic acid deraicvtiavteivneastu, rwalhpicrohduacrtes aanndimphpaorrmtacnetutsiucablscl[a1s–s3]o. fM2o,r3e-dthisaunb1s0t,i0t0u0tebdioilongdicoallelys [a5ct]i,vhe ainvdeoalettracted attentiodneraisvaativpersomhaivseingbepenro-iddernutgifiefodr, aanndticamnocreer tahnand a2n00titduemrivoartiavcetsivairteiescu[r6r,e7n]t.lyInkcnoonwtninuasation of our resepahracrhmaincetuetriecasltsionr 2u-nadmerignooinpgheclninyilcaαl ,tβri-aulsn[s4a]t. uArmatoendg cthaerbinodnoylel sc,o2m-arpooyul ninddsolfeo-3r-atcheeticsyacnidthesis of derivatives, which are an important subclass of 2,3-disubstituted indoles [5], have attracted attention highly faus nacptrioomnaisliinzgepdroi-nddruoglefodr earnitvicaatnicveersan[d8–a1n0ti]t,umwoer arectpivoitritesh[e6r,7e].Itnhceonptrineupaatrioantioofnouorfreasenaorcvhel ethyl 2-[2-(4-ninittreorebset niznoy2-la)-m1iHno-ipnhdeonyl-l3-αy,βl]-aucnestaatutera[t1e1d–1c3ar]b. onyl compounds for the synthesis of highly. Chromatographic purification of the title compound 4 was accomplished using forced-flow chromatography on ICN 60 32-64 mesh silica gel 63 (Merck, Darmstadt, Germany).
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