Abstract
A new pyrrole-substituted terpyridine derivative that possesses an allene moiety was obtained as an “unexpected” sole product during an attempt to alkylate the N-atom of pyrrole with propargyl bromide in order to obtain an alkyne-functionalized terpyridine.
Highlights
IntroductionT[1h]i.s cTahnisbecaenasiblye eeaxspillayinexedplabiynetdhebyhtuhgeehnuugme nbuermobferteorfptyerrpidyirniedidneerdiveartivivaetsivtehsatthactancanbebeoobbtatianinededbbyy vvaarryyiinngg tthhee ssuubbssttiittuuttiioonnppatattetrenrnofothf etlhigealnigdaansdwealsl aws tehlle nasatuthree onfathtuerceomofpltehxeedcommetpalle.xIendpamrteictaull.arI,nteprpayrtriicduinlaers, ttheraptycroindtianiens athfiavtecmonetmaibneraedfivheetemroemcybceler,edsuhchetaesrofcuyrcalne,[2s]uochr tahsiofpuhraenne[2[3]],ohratvheioaptthreanceted[3a], lhoat voef aatttterancttioedn.aInloftaocft,atthteenytcioann.bIne ufascetd, tahseiyntcearnmbeeduiasteeds ians tihneteprmreepdairaatteios ninotfhme aptreerpiaalrsaftoiornsoolfamr caetlelsri[a4ls] oforrnasnoloaprarcteilcllses[4[5]],oars nbaionloopgaicratilcplersob[e5s],[6a]s, absiloigloagnidcaslinpcroatbaelsys[i6s][,7]a,sasliagnatnimdsicirnobciaaltaalgyesnists[[78]],, aass ealnetcitmroicchrorobmiailcamgeantetsri[a8ls],[a9s] oelreacstrcohcrhormomopichomreaste[r1i0a]l,st[o9n] aomr aesjucshtraomfeowphapoprelisca[1ti0o]n, sto
All reagents were purchased from commercial suppliers and used as received
The 1H and 13C NMR spectra were recorded on a Brucker AC 400 (Bruker, Wissembourg, France) at 400 and 100 MHz, respectively, using CDCl3 as a solvent
Summary
T[1h]i.s cTahnisbecaenasiblye eeaxspillayinexedplabiynetdhebyhtuhgeehnuugme nbuermobferteorfptyerrpidyirniedidneerdiveartivivaetsivtehsatthactancanbebeoobbtatianinededbbyy vvaarryyiinngg tthhee ssuubbssttiittuuttiioonnppatattetrenrnofothf etlhigealnigdaansdwealsl aws tehlle nasatuthree onfathtuerceomofpltehxeedcommetpalle.xIendpamrteictaull.arI,nteprpayrtriicduinlaers, ttheraptycroindtianiens athfiavtecmonetmaibneraedfivheetemroemcybceler,edsuhchetaesrofcuyrcalne,[2s]uochr tahsiofpuhraenne[2[3]],ohratvheioaptthreanceted[3a], lhoat voef aatttterancttioedn.aInloftaocft,atthteenytcioann.bIne ufascetd, tahseiyntcearnmbeeduiasteeds ians tihneteprmreepdairaatteios ninotfhme aptreerpiaalrsaftoiornsoolfamr caetlelsri[a4ls] oforrnasnoloaprarcteilcllses[4[5]],oars nbaionloopgaicratilcplersob[e5s],[6a]s, absiloigloagnidcaslinpcroatbaelsys[i6s][,7]a,sasliagnatnimdsicirnobciaaltaalgyesnists[[78]],, aass ealnetcitmroicchrorobmiailcamgeantetsri[a8ls],[a9s] oelreacstrcohcrhormomopichomreaste[r1i0a]l,st[o9n] aomr aesjucshtraomfeowphapoprelisca[1ti0o]n, sto. Analtmhoeujguhstaaliftetwle laepsps lsitcuadtiioends,.tAerlpthyoriudginheas tlihtatlteinlecslsudsteuadipeydr,rtoelrepryinrigdihnaevsethalastoinbceleundaesaupbyjercrtoolef irnintegrehsat.veFoarlseoxabmeepnlea, ssuucbhjetcetropfyirnidteinreesst.hFaovre ebxeaemn pulsee,dsufochr ttheerppyrreipdainraetsiohnavoef cbyeteontouxsiecdmfoolrecthueleps r[e1p1a],rfaotiroanpopfliccyattoiotnoxiinc OmLoEleDcu(loersg[a1n1i]c, floigrhatpepmlicitattiinogn dinioOdLesE)D[1(2o]rgoarnsiecnlsiogrhtdeemviictetisn[g13d]ioodrefso)r[1th2e] oprresepnasroartidonevoicfecsa[t1a3ly]toicr mfoarttehreiaplsr[e1p4a]r.aTtihouns,otfhceaptarleyptiacramtiaotneroiaf ltser[p14y]r.idTihnuesd, ethrievaptrievpeasrtahtaiotncoonftateinrpayfruidnicnteiodnearliivzeadtivpeysrrtholaet icsoonftainintearefsutninctitohneafiliezledds opfybrrootlhe oisrgoafniinctseyrnesttheinsisthaendfiemldasteorfiablostchieonrcgea. For possible future functionalization [15] Analtmhoeujguhstaaliftetwle laepsps lsitcuadtiioends,.tAerlpthyoriudginheas tlihtatlteinlecslsudsteuadipeydr,rtoelrepryinrigdihnaevsethalastoinbceleundaesaupbyjercrtoolef irnintegrehsat.veFoarlseoxabmeepnlea, ssuucbhjetcetropfyirnidteinreesst.hFaovre ebxeaemn pulsee,dsufochr ttheerppyrreipdainraetsiohnavoef cbyeteontouxsiecdmfoolrecthueleps r[e1p1a],rfaotiroanpopfliccyattoiotnoxiinc OmLoEleDcu(loersg[a1n1i]c, floigrhatpepmlicitattiinogn dinioOdLesE)D[1(2o]rgoarnsiecnlsiogrhtdeemviictetisn[g13d]ioodrefso)r[1th2e] oprresepnasroartidonevoicfecsa[t1a3ly]toicr mfoarttehreiaplsr[e1p4a]r.aTtihouns,otfhceaptarleyptiacramtiaotneroiaf ltser[p14y]r.idTihnuesd, ethrievaptrievpeasrtahtaiotncoonftateinrpayfruidnicnteiodnearliivzeadtivpeysrrtholaet icsoonftainintearefsutninctitohneafiliezledds opfybrrootlhe oisrgoafniinctseyrnesttheinsisthaendfiemldasteorfiablostchieonrcgea. nTihcissyanrtthicelseisdeasncdribmeastheroiwal pscyirernoclee.-cTohnitsaianritnicgletedrepsycrriidbienseh1owwapsyorbrotalein-ceodnatasianninugnteexrppeycrtieddinpero1dwuacst doubtrainingeadttaesmapntsutnoepxpreepctaerde cpormodpuocutnddu2ri(nFgigautrteem1)p, wtshtiochpfreeaptaurreescaonmaplokuynnedc2ha(iFnigfourrepo1s),siwblheifcuhtufreeatfuurnecstiaonnaalilzkaytnioenc[h1a5i]n. for possible future functionalization [15]
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