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Molecules 2019, 24, x FOR PEER REVIEW 14 of 42 MolecMuloelsec2u0le1s92,02149,1248,2xFORPEERREVIEW 14 of 42 14of41 Figure 4. 1H-NMR spectra of (a) 2-aminobenzonitrile with (b) [HMIm][Im] (pKa value of cation was Figure 4. 1H-NMR spectra of (a) 2-aminobenzonitrile with (b) [HMIm][Im] (pKa value of cation was Figure 4. 1H-NMR spectra of (a) 2-aminobenzonitrile with (b) [HMIm][Im] (pKa value of cation was 7.1), (c) [HDBU][Im] (pKa value of cation was 11.7) or (d) [HMTBD][Im] (pKa value of cation was 13.0). 7.1), (c)[HDBU][Im] (pKa value of cation was 11.7) or (d) [HMTBD][Im] (pKa value of cation was 7.1), (c)[HDBU][Im] (pKa value of cation was 11.7) or (d) [HMTBD][Im] (pKa value of cation was The H signal of amino in 2-aminobenzonitrile became broader when the basicity of cation was higher. 13.0). The H signal of amino in 2-aminobenzonitrile became broader when the basicity of cation was 13.0). The H signal of amino in 2-aminobenzonitrile became broader when the basicity of cation was Reprinted with permission from [81] (Copyright 2018 American Chemical Society). higher. Reprinted with permission from [81] (Copyright 2018 American Chemical Society). higher. Reprinted with permission from [81] (Copyright 2018 American Chemical Society). Inspired by Dyson’s work, Fujita et al. found that nBu4NF was an effective quaternary ammonium nn InspInirsepdirebdybyDyDsyosno’ns’swwoorrkk,, Fujita ett aal.l. fofouundndthtaht atBuB4NuF4NwFaswans eafnfecetifvfectqiuvaeteqrnuaartyernary salt for catalyzing the cyclization of 2-aminobenzonitriles when a catalyst loading of 1 mol% was used ammonium salt for catalyzing the cyclization of 2-aminobenzonitriles when a catalyst loading of 1 ammonium salt for catalyzing the cyclization of 2-aminobenzonitriles when a catalyst loading of 1 at 110 ◦C under CO2 pressure of 2 MPa for 24 h [56]. mol% was used at 110 °C under CO2 pressure of 2 MPa for 24 h [56]. mol% was used at 110 °C under CO2 pressure of 2 MPa for 24 h [56]. As introduced in Section 2.2.1 of this review, cyanuric acid-based organocatalystw could be good As introduced in Section 2.2.1 of this review, cyanuric acid-based organocatalystw could be As introduced in Section 2.2.1 of this review, cyanuric acid-based organocatalystw could be activgaotodrsafoctrivCaOtorscafporturCeOa2ndcauptiulrizeatainodn [u58ti]l.iz[aEtitonN][5[8C].YA[E]tw4Na]s3[CalYsAo]anweafsficaielsnot oarngaenffoiciaetnatlyst in 243 good activators for CO2 capture and utilization [58]. [Et4N]3[CYA] was also an efficient convoerrgtainogcatmalyostphinerciconpvrerstsiungreaotfmCoOsphienrtiocqpureinssauzroelinoef-2C,O4(21Hin,t3oH)q-udiinoanzeosliwnei-t2h,4o(u1tHa,3nHy)e-dxitoenrnesalbase 2 organocatalyst in converting atmospheric pressure of CO2 into quinazoline-2,4(1H,3H)-diones without any external base or promoter. or promoter. without any external base or promoter. In recent years, great efforts have been made to develop heterogeneous catalysts for a greener In recent years, great efforts have been made to develop heterogeneous catalysts for a greener In recent years, great efforts have been made to develop heterogeneous catalysts for a greener procedure to quinazoline-2,4(1H,3H)-dione. Both a graphitic carbon nitride catalyst [82] and a procedure to quinazoline-2,4(1H,3H)-dione. Both a graphitic carbon nitride catalyst [82] and a procfeudnuctrioenatolizqeduibnaasziconlianneo-c2r,y4s(1taHll,i3nHe z)-edoiloitnee[8.3B] optrheparegdrabpyhSirtiivcasctavrbaoent anl.iwtreidredceamtaonlysstrtat[e8d2]toand a functionalized basic nanocrystalline zeolite [83] prepared by Srivastava et al. were demonstrated to be funcbteioneaflfiezcetdivebasinc nathneocrsysnttahlelisnise zoefolitqeu[i8n3a]zoplirneep-a2,r4e(d1Hb,y3HS)r-divioansteavafroemt al. twhererdeaecmtionstoraf ted to effective in the synthesis of quinazoline-2,4(1H,3H)-dione from the reaction of 2-aminobenzonitrile 2-aminobenzonitrile and CO2 (Scheme 13). be effective in the synthesis of quinazoline-2,4(1H,3H)-dione from the reaction of and CO2 (Scheme 13). 2-aminobenzonitrile and CO2 (Scheme 13). Scheme 13. Synthesis of quinazoline-2,4(1H,3H)-dione by heterogeneous catalysts. In recent years, much attention was paid to the synthesis of quinazoline-2,4(1H,3H)-diones via Scheme 13. Synthesis of quinazoline-2,4(1H,3H)-dione by heterogeneous catalysts. Scheme 13. Synthesis of quinazoline-2,4(1H,3H)-dione by heterogeneous catalysts. the multicomponent reactions involving CO2 (Scheme 14). In 2017, Cheng et al. reported pIanllardeicuemnt-cyateaalyrsz,edmmuuclhticaotmtepnotnioent wreasctipoanisdotfoOt-ahlekysnyynlathnelisniess,oafryqluiiondaidzeosl,inaen-d2,a4t(m1oHs,p3hHer)i-cdiones In recent years, much attention was paid to the synthesis of quinazoline-2,4(1H,3H)-diones via pressure of CO2, generating 3,3-diaryl 2,4-quinolinediones [84]. This reaction provided a one pot via the multicomponent reactions involving CO2 (Scheme 14). In 2017, Cheng et al. reported the multicomponent reactions involving CO2 (Scheme 14). In 2017, Cheng et al. reported palladium-catalyzed multicomponent reactions of O-alkynylanlines, aryl iodides, and atmospheric palladium-catalyzed multicomponent reactions of O-alkynylanlines, aryl iodides, and atmospheric pressure of CO2, generating 3,3-diaryl 2,4-quinolinediones [84]. This reaction provided a one pot pressure of CO2, generating 3,3-diaryl 2,4-quinolinediones [84]. This reaction provided a one pot strategy to incorporate CO2 into heterocycles bearing a quaternary carbon center (Scheme 14a). As shown in Scheme 14c, the carboxylation of amine with CO2 and the trans-oxopalladation ofPDF Image | Catalytic Conversion of Carbon Dioxide through C-N Bond
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