Recent Advances in Diversity-oriented Synthesis of N-containing Organic Molecules Through Carbodiimide-based Reactions

References

1. KnoxJ.R. ToiaR.F. CasidaJ.E. Insecticidal thioureas: Preparation of [phenoxy-4-3H]diafenthiuron, the corresponding carbodiimide, and related compounds.J. Agric. Food Chem.199240590991310.1021/jf00017a043
   [Google Scholar]
2. MolinaP. AlajarinM. VidalA. Sanchez-AndradaP. C=C-conjugated carbodiimides as 2-aza dienes in intramolecular [4+2] cycloadditions. One-pot preparation of quinoline. alpha.-carboline, and quinindoline derivatives.J. Org. Chem.199257392993910.1021/jo00029a026
   [Google Scholar]
3. JohnsonJ.D. KaplanS.W. TothJ. WangZ. MawM. SheikoS.S. ZhukhovitskiyA.V. Carbodiimide ring-opening metathesis polymerization.ACS Cent. Sci.2023961104111010.1021/acscentsci.3c00032 37396860
   [Google Scholar]
4. RebekJ. FeitlerD. Peptide synthesis with carbodiimide.Int. J. Pept. Protein Res.19757216716910.1111/j.1399‑3011.1975.tb02428.x 1095505
   [Google Scholar]
5. KhoranaH.G. 387. Peptides. Part III. Selective degradation from the carboxyl end. The use of carbodi-imides.J. Chem. Soc.195202081208810.1039/jr9520002081
   [Google Scholar]
6. LinY.H. LiJ. QinY. WangH. GuptaS. Carbodiimide scaffolds: Efficient and versatile reagents in synthesis of heterocycles.Synth. Commun.202151182713273110.1080/00397911.2021.1953533
   [Google Scholar]
7. WilliamsA. IbrahimI.T. Carbodiimide chemistry: recent advances.Chem. Rev.198181658963610.1021/cr00046a004
   [Google Scholar]
8. BellucciM.C. VolonterioA. Carbodiimides-mediated multi component synthesis of biologically relevant structures.Organic Chemistry Insights2012412410.4137/OCI.S9112
   [Google Scholar]
9. WangY. ZhangW.X. XiZ. Carbodiimide-based synthesis of N-heterocycles: moving from two classical reactive sites to chemical bond breaking/forming reaction.Chem. Soc. Rev.202049165810584910.1039/C9CS00478E 32658233
   [Google Scholar]
10. KurzerF. Douraghi-ZadehK. Advances in the chemistry of carbodiimides.Chem. Rev.196767210715210.1021/cr60246a001 4859920
    [Google Scholar]
11. PeddaraoT. BaishyaA. BarmanM.K. KumarA. NembennaS. Metal-free access of bulky N,N′-diarylcarbodiimides and their reduction: bulky N,N′-diarylformamidines.New J. Chem.20164097627763610.1039/C6NJ00907G
    [Google Scholar]
12. PublicationA. 1-ethyl-3-(3-dimethylamino)propylcarbodiimide hydrochloride and methiodide.Org. Synth.196848September8310.15227/orgsyn.048.0083
    [Google Scholar]
13. MonagleJ.J. Carbodiimides. III. Conversion of Isocyanates to Carbodiimides. Catalyst Studies.J. Org. Chem.196227113851385510.1021/jo01058a022
    [Google Scholar]
14. MalviyaB.K. JaiswalP.K. VermaV.P. BadsaraS.S. SharmaS. Electrochemical synthesis of carbodiimides via metal/oxidant-free oxidative cross-coupling of amines and isocyanides.Org. Lett.20202262323232710.1021/acs.orglett.0c00510 32142299
    [Google Scholar]
15. ZhangZ. TanP. ChangW. ZhangZ. Transition‐metal‐catalyzed cross‐coupling and sequential reactions of azides with isocyanides.Adv. Synth. Catal.2021363245344535910.1002/adsc.202101107
    [Google Scholar]
16. RooseT.R. VerdoornD.S. MampuysP. RuijterE. MaesB.U.W. OrruR.V.A. Transition metal-catalysed carbene and nitrene transfer to carbon monoxide and isocyanides.Chem. Soc. Rev.202251145842587710.1039/D1CS00305D 35748338
    [Google Scholar]
17. ChenH. LiuM.G. Synthesis, characterization and crystal structure of heterocyclic tetrahydropyrido[4′,3′:4,5]thieno[2,3-d]pyrimidinone derivatives via sequential aza-Wittig/base catalyzed cyclization.J. Mol. Struct.20191180314010.1016/j.molstruc.2018.11.091
    [Google Scholar]
18. FangZ.D. WeiX.H. One-pot three-component synthesis of 1,4-bis[thiazolo[4,5-d]pyrimidin-7(6 H)-one]piperazine derivatives.J. Chem. Res.2012361061261410.3184/174751912X13460803277147
    [Google Scholar]
19. FangZ.D. FangD. ChengQ. Sequential three-component synthesis of 1,4-bis[6,9-dihydro-6-oxo-9-phenyl-1 H -purin-2-yl]piperazines.J. Chem. Res.2012361270370510.3184/174751912X13505755737168
    [Google Scholar]
20. MengS. JiaZ. WangK. FanY. GuoY. Facile synthesis of Thieno[2,3- d]pyrimidine derivatives using inorganic base catalysis.Synth. Commun.201444101461146510.1080/00397911.2013.859705
    [Google Scholar]
21. FangD. Z.; Hong Wei, X. Sequential Three-Component Synthesis of 1,4-Bis[triazolo[4,5-d]pyrimidin-7(6H)-one]piperazines.Heterocycles201285112757276310.3987/COM‑12‑12564
    [Google Scholar]
22. BellucciM.C. VolonterioA. Three-component sequential synthesis of N,N′-disubstituted 5-arylidenedihydropyrimidine-2,4-dione.Tetrahedron Lett.201253354733473710.1016/j.tetlet.2012.06.109
    [Google Scholar]
23. DuangjanC. RukachaisirikulV. SaithongS. KaeobamrungJ. Copper-catalyzed domino reaction of carbodiimides and benzoic acid derivatives for the synthesis of quinazolinediones.Tetrahedron Lett.201859393537354010.1016/j.tetlet.2018.08.028
    [Google Scholar]
24. WeischedelH. SchmidtD. ConradJ. BeifussU. Formation of substituted 2-iminooxazolidines via intermolecular 1,2-addition/intramolecular N-vinylation using 3-substituted-2-bromo-2-propen-1-ols as substrates.Tetrahedron201874446426644110.1016/j.tet.2018.08.051
    [Google Scholar]
25. LiaoP. BiX. YiX. BarryB-D. Synthesis of N-Sulfonylazetidin-2-imines via the Copper(I) oxide catalyzed multicomponent reaction of alkynes, sulfonyl azides and diimines under solvent-free conditions.Synthesis20124491323132810.1055/s‑0031‑1289740
    [Google Scholar]
26. WangF. CaiS. LiaoQ. XiC. A protocol to 2-aminobenzimidazoles via copper-catalyzed cascade addition and cyclization of o-haloanilines and carbodiimides.J. Org. Chem.20117693174318010.1021/jo200014v 21413745
    [Google Scholar]
27. ShenG. ChenD. ZhangY. SunM. ChenK. JinC. LiK. BaoW. Synthesis of benzoxazine and 1,3-oxazine derivatives via ligand-free copper(I)-catalyzed one-pot cascade addition/cyclization reaction.Tetrahedron201268116617210.1016/j.tet.2011.10.075
    [Google Scholar]
28. ChiY. YanH. ZhangW.X. XiZ. CuOTf‐catalyzed selective generation of 2‐aminopyrimidines from carbodiimides and diaryliodonium salts by a triple C(sp 3)−H functionalization.Chemistry201723475776110.1002/chem.201604739 27898999
    [Google Scholar]
29. LiuY. LiZ. JiangL. ZhengA. An efficient synthesis of 3‐alkyl‐2‐alkyliminooxazolidin‐4‐one via a domino reaction.Chin. J. Chem.201129230330810.1002/cjoc.201190082
    [Google Scholar]
30. DasS. BhattacharjeeJ. PandaT.K. Guanylation/cyclisation of amino acid esters using an imidazolin-2-iminato titanium initiator.Dalton Trans.201948217227723510.1039/C8DT04630A 30688333
    [Google Scholar]
31. ShenH. ChanH.S. XieZ. Guanylation of amines catalyzed by a half-sandwich titanacarborane amide complex.Organometallics200625235515551710.1021/om060811x
    [Google Scholar]
32. ShenH. WangY. XieZ. Ti-amide catalyzed synthesis of cyclic guanidines from di-/triamines and carbodiimides.Org. Lett.201113174562456510.1021/ol201752e 21815662
    [Google Scholar]
33. XieZ. WangY. ShenH. Atom-economical synthesis of 2-aminoimidazoles via [3+2] annulation catalyzed by titanacarborane monoamide.Synlett20112011796997310.1055/s‑0030‑1259713
    [Google Scholar]
34. AmanH. HuangY.C. LiuY.H. TsaiY.L. KimM. HsiehJ.C. ChuangG.J. Cobalt-catalyzed cyclization of 2-bromobenzamides with carbodiimides: A new route for the synthesis of 3-(imino)isoindolin-1-ones.Molecules20212623721210.3390/molecules26237212 34885794
    [Google Scholar]
35. TanakaK. MimuraM. HojoD. Synthesis of substituted 6-imino-2-piperidinones by Rh-catalyzed [4+2] annulation of 4-alkynals with carbodiimides.Tetrahedron200965449008901410.1016/j.tet.2009.06.115
    [Google Scholar]
36. ChiY. XuL. DuS. YanH. ZhangW.X. XiZ. Synthesis and mechanistic study of cyclic oxoguanidines via Zn(OTf) 2 ‐catalyzed guanylation/amidation from readily available amino acid esters and carbodiimides.Chemistry20152129103691037810.1002/chem.201500573 26013660
    [Google Scholar]
37. LuC. GongC. ZhaoB. HuL. YaoY.R.E. [N(SiMe 3) 2] 3 -catalyzed guanylation/cyclization of amino acid esters and carbodiimides.J. Org. Chem.20188331154115910.1021/acs.joc.7b02550 29337548
    [Google Scholar]
38. ChiY. YanH. ZhangW.X. XiZ. Synthesis of quinoline derivatives via cu-catalyzed cascade annulation of heterocumulenes, alkynes, and diaryliodonium salts.Org. Lett.201719102694269710.1021/acs.orglett.7b01025 28481555
    [Google Scholar]
39. Samzadeh-KermaniA. GhasemiS. A catalytic route to pyrrole derivatives via copper‐catalyzed multicomponent reaction.J. Heterocycl. Chem.20195682202220910.1002/jhet.3614
    [Google Scholar]
40. ZhaoF. LiY. WangY. ZhangW.X. XiZ. Selective synthesis of (Z)-2-enynyl-2-hydroxy-imidazolidine-4,5-diones via Cu(i)-mediated multicomponent coupling of terminal alkynes, carbodiimides and oxalyl chloride.Org. Biomol. Chem.201412213336333910.1039/C4OB00185K 24723221
    [Google Scholar]
41. QiuG. LuY. WuJ. A concise synthesis of 4-imino-3,4-dihydroquinazolin-2-ylphosphonates via a palladium-catalyzed reaction of carbodiimide, isocyanide, and phosphite.Org. Biomol. Chem.201311579880210.1039/C2OB26979A 23229113
    [Google Scholar]
42. WangY. ZhaoF. ZhouY. ChiY. WangZ. ZhangW.X. XiZ. Mechanistic study on the cleavage and reorganization of C(sp3)-H and C=N bonds in carbodiimides: synthesis of 1,2-dihydrothiopyrimidines and 2,3-dihydropyrimidinthiones through four-component coupling.Chemistry20131932106431065410.1002/chem.201301633 23821475
    [Google Scholar]
43. ZhangX. WangS. LiuY. XiC. Triflates-triggered intermolecular cyclization of carbodiimides leading to 2-aminoquinazolinone and 2,4-diaminoquinazoline derivatives.Org. Lett.20182082148215110.1021/acs.orglett.8b00314 29620371
    [Google Scholar]
44. AsadiM. EbrahimiM. MahdaviM. SaeediM. RanjbarP.R. YazdaniF. ShafieeA. ForoumadiA. Reaction of isatoic anhydride, amine, and N,N ′-dialkyl carbodiimides under solvent-free conditions: New and efficient synthesis of 3-alkyl-2-(alkylamino)quinazolin-4(3 H)-ones.Synth. Commun.201343172385239210.1080/00397911.2012.714042
    [Google Scholar]
45. UlrichH. TuckerB. SayighA.A.R. Methyl-tert-butylcarbodiimide. Diagnostic tool in 2 + 2 cycloaddition reactions.J. Am. Chem. Soc.197294103484348710.1021/ja00765a039
    [Google Scholar]
46. ShainyanB.A. TolstikovaL.L. SterkhovaI.V. Unusual [2+2]-cycloaddition of carbodiimides to N-alkenylidenetriflamides.Tetrahedron Lett.201657394440444210.1016/j.tetlet.2016.08.078
    [Google Scholar]
47. ShainyanB.A. TolstikovaL.L. Reaction of N-sulfinyltrifluoromethanesulfonamide with carbodiimides: Formation of N-trifluoromethanesulfonyl-2,4-dialkyl-1,2,4-thiadiazetidin-3-imine 1-oxides.J. Fluor. Chem.2012140596110.1016/j.jfluchem.2012.04.016
    [Google Scholar]
48. SrivastavaV. SinghP.K. SinghP.P. Recent advances of visible-light photocatalysis in the functionalization of organic compounds.J. Photochem. Photobiol. Photochem. Rev.20225010048810.1016/j.jphotochemrev.2022.100488
    [Google Scholar]
49. Meza-LeónR.L. BernèsS. Cortés-LópezG.N. MastranzoV.M. Sosa-RivadeneyraM. Sartillo-PiscilF. Synthesis of 5-hydroxy hydantoins via a tandem process.Tetrahedron Lett.201657374232423410.1016/j.tetlet.2016.08.022
    [Google Scholar]
50. KasatkinaS. StepanovaE. DmitrievM. MokrushinI. MaslivetsA. Divergent synthesis of (quinoxalin-2-yl)-1,3-oxazines and pyrimido[1,6-a]quinoxalines via the cycloaddition reaction of acyl(quinoxalinyl)ketenes.Tetrahedron Lett.2019603915108810.1016/j.tetlet.2019.151088
    [Google Scholar]
51. JohnstonJ.R. WestF.G. Regioselective synthesis of 2-iminooxazinones from dioxinones and carbodiimides.Tetrahedron Lett.201253415479548210.1016/j.tetlet.2012.07.100
    [Google Scholar]
52. SilvaA. TalhiO. PintoD. Synthesis of 5-(2-hydroxybenzoyl)-1,3-disubstituted uracils.Synlett20132491147114910.1055/s‑0033‑1338932
    [Google Scholar]
53. SarmahB.K. KonwarM. DasA. Site-selective deoxygenative amination of azine N -oxides with carbodiimides under catalyst-, activator-, base-, and solvent-free conditions.J. Org. Chem.20218615107621077210.1021/acs.joc.1c00741 34260234
    [Google Scholar]
54. YuQ. YuJ. BaoH. HuX. YingD. WuL. LiuF. JiangH. JinxiaZ. ZhangS. Naturally occurring bioactive 5-ethylidenehydantoins as inspiration for the development of analogues.Synth. Commun.201848151939194410.1080/00397911.2018.1467457
    [Google Scholar]
55. AlizadehA. RezvanianA. Isoquinoline-catalyzed reaction of phenacyl bromide and N,N-Dialkyl¬carbodiimides: Novel synthesis of azirines.Synlett201223685986210.1055/s‑0031‑1290487
    [Google Scholar]
56. YenW.P. KungF.C. WongF.F. 1,3‐dipolar cycloaddition of carbodiimides and nitrilimines: Synthesis and mechanistic study of 5‐amino‐1,2,4‐triazoles.Eur. J. Org. Chem.20162016132328233510.1002/ejoc.201600240
    [Google Scholar]
57. OlimpieriF. BellucciM.C. MarcelliT. VolonterioA. Regioselective multicomponent sequential synthesis of hydantoins.Org. Biomol. Chem.201210489538955510.1039/c2ob26498f 23075991
    [Google Scholar]
58. TalhiO. FernandesJ.A. PintoD.C.G.A. Almeida PazF.A. SilvaA.S.M. Diastereoselective synthesis of benzofuran-3(2H)-one-hydantoin dyads.Tetrahedron201369265413542010.1016/j.tet.2013.04.111
    [Google Scholar]
59. HeX. YangC. WuY. XieM. LiR. DuanJ. ShangY. Synthesis of unsymmetrical urea derivatives via one-pot sequential three-component reactions of cyclic 2-diazo-1,3-diketones, carbodiimides, and 1,2-dihaloethanes.Org. Biomol. Chem.202018224178418210.1039/D0OB00683A 32441722
    [Google Scholar]
60. WangH. YeS. JinH. LiuJ. WuJ. An expeditious approach to 1-(isoquinolin-1-yl)guanidines via a three-component reaction of 2-alkynylbenzaldehyde, sulfonohydrazide, with carbodiimide.Tetrahedron201167335871587710.1016/j.tet.2011.06.056
    [Google Scholar]
61. PanahiF. JamediF. IranpoorN. Nickel‐catalyzed reductive addition of aryl/benzyl halides and pseudohalides to carbodiimides for the synthesis of amides.Eur. J. Org. Chem.20162016478078810.1002/ejoc.201501349
    [Google Scholar]
62. WangS. ZhangY. LiuG. XuH. SongL. ChenJ. LiJ. ZhangZ. Transition-metal-free synthesis of 5-amino-1,2,3-triazoles via nucleophilic addition/cyclization of carbodiimides with diazo compounds.Org. Chem. Front.20218359960410.1039/D0QO01288B
    [Google Scholar]
63. YeS. WangH. WuJ. 1-(isoquinolin-1-yl)urea library generation via three-component reaction of 2-alkynylbenzaldoxime, carbodiimide, with electrophile.ACS Comb. Sci.201113212012510.1021/co100026y 21395340
    [Google Scholar]
64. YeS. WangH. WuJ. An expeditious approach to 1-aminoisoquinolines via an unexpected reaction of 2-alkynylbenzaldoxime, carbodiimide, with bromine.Tetrahedron201167254628463210.1016/j.tet.2011.04.063
    [Google Scholar]
65. ShiJ. LiL. LiY. o -silylaryl triflates: A journey of kobayashi aryne precursors.Chem. Rev.202112173892404410.1021/acs.chemrev.0c01011 33599472
    [Google Scholar]
66. LiR. TangH. FuH. RenH. WangX. WuC. WuC. ShiF. Arynes double bond insertion/nucleophilic addition with vinylogous amides and carbodiimides.J. Org. Chem.20147931344135510.1021/jo402754d 24433159
    [Google Scholar]
67. ThirupathiA. JanniM. PeruncheralathanS. Copper catalyzed intramolecular N-arylation of ketene aminals at room temperature: Synthesis of 2-amino-3-cyanoindoles.J. Org. Chem.201883158668867810.1021/acs.joc.8b00816 29847946
    [Google Scholar]
68. WangY. ChiY. ZhaoF. ZhangW.X. XiZ. ChemInform Abstract: Synthesis, characterization, and reactivity of N‐Acyl Chloroformamidines: Useful building blocks for the construction of N‐Acyl substituted 1,1‐diaminoethylenes, amidines, ureas, and thioureas. ChemInform,20134421chin.20132107710.1002/chin.201321077