Abstract
A simple and highly efficient protocol for the synthesis of derivatives 7, 7-dimethyl-4-phenyl-2-thioxo-2, 3, 4, 6, 7, 8-hexahydro-1H-quinazoline-5-one from 5, 5-dimethyl cyclohexane-1, 3-dione (4a–4h) (dimedone) has been described. The aryl aldehydes were substituted with thiourea in the presence of synthesized zinc ferrite nanocatalyst, which increased the yield under reflux through condensation, followed by cyclization to give desired products. The other advantages are that it is eco-friendly and economically affordable for large-scale production. Structural validation and characterization of all the newly synthesized compounds were evaluated by spectral analysis (mass spectrometry, proton nuclear magnetic resonance (1HNMR), and Carbon-13 nuclear magnetic resonance(13CNMR)spectroscopies. The structure of antibacterial and antifungal assays was performed with the newly synthesized compounds. The antimicrobial activity of title compounds possessing electron-withdrawing groups such as (4e–4h) (Cl, Br, and cyano group) exhibited more active potential than the electron-donating groups, C6H5,4-C6H4, 3-OC2H5-4OH-C6H3, etc., (4a–4d) containing moiety.
Highlights
Multicomponent reaction (MCR) is the most powerful and efficient technique in modern synthetic organic chemistry
Dimedone called 5, 5-dimethylcyclohexane-1, 3-dione is a cyclic diketone, which is used as a key sample molecule for the synthesis of the various moiety in synthetic organic chemistry
Chemicals, and solvents (Merck, Mumbai, India) were procured and the melting points of the newly synthesized compounds were determined by using Agrawal 535 melting point apparatus
Summary
Multicomponent reaction (MCR) is the most powerful and efficient technique in modern synthetic organic chemistry. The advantages of these reactions in synthetic organic chemistry are the valuable characteristics such as constructing desired compounds, straightforward reaction design, atom economy, and the simple purification of target products. The six-membered heterocyclic compounds such as hexahydroquinazolinones in medicinal chemistry and synthetic organic chemistry are of special interest. The main focus on the synthesis of derivatives of 7,7-dimethyl-4phenyl-2-thioxo-1,2,3,4,6,7,8-hexahydro-1H-quinazoline-5-ones has considerably attracted. Catalysts 2021, 11, 431 of 7,7-dimethyl-4-phenyl-2-thioxo-1,2,3,4,6,7,8-hexahydro-1H-quinazoline-5-ones has considerably attracted attention in recent years due to their potential, antioxidant [4], aatntetinfutinognailn, raencteibnatcyteerairasl,daunetittoutmhoeirr, paontdenatniatli,tuabnetirocxuildaar natc[t4iv],itaynt[i5f]uwnigtahl,wanidtiebaacptperliicaal,atniotnitsu,minocrl,uadnidnganatnittuicboenrcvuulalsraanctt,ivseitdya[t5iv] ew, ittrhawnqidueiliazpepr,liacantaiolgness,iicn[c6lu,7d],inagntainmtiiccoronbviualls,aannt,seesdthaetitvice,[t8r]a,naqnutiicliaznecr,earn[a9l]g, easnictih[6y,7p]e,ratenntismiviecr[o1b0i]a,l,aanntie-sinthfleatmicm[8a],toarnytic[1a1n]c,edri[u9r]e, tainc t[ih12y]-, paenrdtemnsuivscele[1r0e],laaxnatni-tinpflraompemrtaietos r[y13[1].1T],hdeiuvraertiiocu[s12o]r,gaanndicmturasnclseforremlaaxtainont prreoapcteirotniessw[1e3r]e. Tehmepvloayrieodubs yortghaenuiscetroafntsrfimoremthaytilosinlyrlecahcltoiornidsew[1e4r]e. eTmheprleoyareedfbewy trheepourstes ofofrtrtihme estyhnytlhsei-lsyils chofloroicdtea [1h4y]d. rToheqrueinaarzeofleinwonreepodretrsivfoatrivthese suysninthgescisatoalfyosctsta shuycdhroasqucionnazceonlitnraotneed dHe2rSivOa4t[i1v5e]s, uNsainfigonc-aHtal[y1s6t]s, sNuHch4VasOc3o[1n7c]e,nstirliactae-dsuHlf2uSrOic a[c1i5d],[N18a]fi, oann-dHa[l1s6o],inNiHon4VicOli3q[u1i7d]s, s[iHlicMa-IsMul]fuHri2cSOac4idin[1p8r]e, saenndcealosof TinMioSnCicl [li1q9u],id[sBM[HIMMI]MBr]-[HB2MSOIM4 ]inBFp4r[e2s0e]n, caendofZTrOMCSCl2.l8[H192O], [[B2M1]I.MTh]Bisr-a[rBtMiclIeMte]BnFd4s [t2o0r]e, panodrtZthrOe sCyln2.th8Hes2isOo[f271,].7T-dhiims aetrhtiycle-4t-epnhdesntyol-r2e-pthoirotxtho-e2s,y3n, t4h,e6-, s7i,s of87-,h7e-xdaimhyedthroy-l-14H-p-qhueninyal-z2o-tlihni-o5x-oo-n2e, s3, 4,u6s,i7n,g8-henxaanhoycdartoa-l1yHst-.quiLnanzothliann-5u-monesduospinegd nNain0o.6cZanta0l.2yFset.2-LXaLnatXhaOn4um(x=d0o.0p7e5d) Nfeir0r.i6tZe nw0a.2sFed2e-vXeLloapXeOd4b(xy =A0m.0o7l5)etfearlr.itTehwisasfedrerivtelohpaesda bsypiAnaml ocul ebticals.trTuhcitsufreerarintedhaalsatatiscpeicnoanl sctuabnitcosftr8u.4c8tu6.reThanedFearrlaot-tsipceincaolnssatmanptleofw8a.4s8u6s.eTdhaes
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