Abstract
An efficient and convenient method to synthesize highly functionalized 3,7′-bisindole derivatives has been developed via a Michael addition and cyclic condensation reaction of heterocyclic ketene aminals (HKAs) with 2-(1H-indol-3-yl)cyclohexa-2,5-diene-1,4-dione derivatives in ethanol-based solvents at room temperature. This strategy provides an efficient, environmentally friendly approach for easy access to various novel 3,7′-bisindole derivatives in moderate to good yields.
Highlights
Adebrsitvraatcitv:eAs nhaesffibcieeennt adnedveclonpvedeniveinat amMethicohdaetol asdyndtihtieosnizeanhdigchylyclifcunccotniodneanlsizaetidon3,7r′e-abcistinondoolef dherteivroatciyvcelsichkaestbeeneenadmevinealolsp(eHdKvAiasa) Mwitchha2e-(l1aHdd-iintidoonl-a3n-ydlc)cyycclilcochoenxda-e2n,5sa-dtiioennere-1a,c4t-idonioonfehdeeterirvoactyicvleics kineteetnheanaoml-ibnaslsed(HsoKlAvesn) tws aitthro2o-(m1Hte-imndpoelr-a3t-uyrl)ec.yTchloishesxtraa-t2e,5g-ydpiernoev-i1d,4e-sdaionneeffidceierinvta, teivnevsiroinnmetehnatnaolllybfraiseenddlsyolvapenptrsoatchrofoomr teeamsypearcacteusrse.tTohvisarsitorautsegnyopvreol v3id,7e1-sbaisninedffoicleiendte, reinvvatiirvoensmienntmalolydefrriaetnedltyo agpopodroyaicehldfos.r easy access to various novel 3,7′-bisindole derivatives in moderate to good yields
Synthesis of 3,7′-bisindole derivatives based on the HKAs. 2
We have successfully developed a facile, economical, and environmentally friendly method for the construction of highly functionalized 3,71-bisindole derivatives via a Michael addition/cyclocondensation reaction. This allowed for the rapid construction of a novel library of highly substituted 3,71-bisindole derivatives through the simple and easy raw material HKAs 1 and 2-(1H-indol-3-yl)cyclohexa-2,5-diene-1,4-dione derivatives 2
Summary
Bisindoollee--ccoonnttaaiinniinngg ssyysstteemmss aarree pprreevvaalleenntt mmoolleeccuullaarr aarrcchhiitteeccttuurreess tthhaatt aarre widely found in naturall products [1–4]. FFuurrtthheerrmmoorree,, bbiissiinnddoollee ddeerriivvaattiivveessaarree essppeecciiaallllyy iimmppoorrttaanntt [[55––88]] dduuee to their potent biological activities, including methicillin-resistant S. aureus (MRSA) pyruvate kinase inhibitors (cis-3,4-dihhyyddrroohhaammaaccaanntthhiinn aanndd ssppoonnggoottiinnee AA,, FFiigguurree 11)) [[99––1111]],, aannttiittuummoorr aaggeennttss ((HHyyddrrooxxyy CCBB11,, Figure 1) [[1122––1144]],,aannttiihhiissttaammiinneessaannddaanntitmimicircorobbiailasls[1[51]5,]a, natni-tin-iflnaflmammmataotroiersie[s16[1],6a],natinbtaibctaecrtiearlisaalsnadnsdo soon o[1n7,[1187],.1B8e].caBuesceauosfethoefirtuhneirquuenbiqiouleogbiicoalloagcitciavlitaiecst,ivmitoieres,amndorme oarnedsymntohreetiscysntrtahteetgiciesttroatgeegniesrattoe gbeisninerdaotelebsiksienledtoolnesshkaevleetobnesenhadveevebleoepned.eveloped. Lewis acids as well as Brønsted acids are employed as catalysts to form bisindole derivGateinveesrasltlayr, tinLgewfriosmaciniddsoleass rewaectlledaws itBhrøcnarsbteodnyal cciodms paoruendesmapnldoytehdeirassynctahteatliycstesqutiovafleonrmts [b1i9s–in2d9]o.leHdoewrievvaetri,vethsestsayrntitnhgetfircopmatihnwdoalyess orefahcitgehdlywiftuhnccatirobnoanliyzlecdombipsionudnodles danerdivtahteiviressyunstuhaeltliyc seuqfufievraflreonmtsc[o1m9–m29o]n. Hlimowiteavtieorn, sth, ienscylundthinegtichaprasthhwreaayctsioonf hcoignhdliytifounnsc,tmiounlatilsizteepd rbeiascintidoonlse, udseeriovfattoivxeics suosluvaelnlyts,saunfdfecrofsrtolymcactoamlymstsoonrleimnziytamtieosn[s3,0i]n. Ccloundsienqguhenatrlsyh, trheeadcteivoenlocpomndeintitoonfsm, morue lsttirsatiegphtrfeoarcwtiaornds,, eucsoe-forfietnoxdilcysaonldveenftfsic,iaenndt sctorasttelygiceastaislyhsitgsholyr ednezsiyrmabelse [f3o0r]t.hCeosnysnetqhueseinstolyf,bthiseinddeovleelso. SubstMitouletceudles i2n01d6o, 2l1e, 6d38erivatives based on HKA building blocks [50–52] (Figure 2). W2 oef 1r1eport anMeoflfiaecncuileeesfnf2it0c1ai6en,n2dt1,ac6no3d8nccoisnecipseropcreoscsestsotcoocnosntsrtuructcthhigighhllyy ffuunnccttiioonnaalilziezded3,37′,-7b1i-sbinisdinoldeodleerdiveartiivveastivvieas2aovnfi1a1 an enavnireoenfnfvmiicrieoennntmtaaellnnydtaflrcliyoennfrcdiieslnyedaplynrodacnehdsisghhitgolhyclyosenslseetlcretucitcvitveehoiongnhee-l-pypoofttuppnrcrootittooonccoaoll.li.zed 3,7′-bisindole derivatives via an environmentally friendly and highly selective one-pot protocol. Synthesis of 3,7′-bisindole derivatives based on the HKAs
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