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image of Bis(α-Cyanoacetamides): Versatile Intermediates for the Synthesis of Diverse Heterocyclic and Macrocyclic Molecular Systems

Abstract

This review examines the reactivity of bis(α-cyanoacetamides) attached to various spacers in producing heterocyclic and macrocyclic molecules. Bis(α-cyanoacetamides) contain two electrophilic and three nucleophilic sites, allowing for multiple coupling reactions. They are regarded as potent chemical reagents capable of producing various heterocyclic derivatives with potential biological applications. The current review covers all reports where bis(α-cyanoacetamides) are used to prepare heterocycles with mono-, bi-, and tricyclic rings. The review is divided into sections based on the type of annulation system and the number of heteroatoms present. We reviewed all available papers on synthesizing macrocyclic molecular systems using bis(α-cyanoacetamide). The mechanistic postulates of some complex procedures are highlighted.

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2025-02-04
2025-05-03
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References

  1. Shi X.L. Lv Y. Zhang T. Hu Q. Shi K. Zhang W. Li Z. Polyetheretherketone fiber-supported TBD as an efficient fibrous superbase catalyst for organic conversions in continuous-flow processing. J. Catal. 2023 418 110 120 10.1016/j.jcat.2023.01.010
    [Google Scholar]
  2. Fadda A.A. Rabie R. Cyanoacetylation of amines: recent advances in preparation methods and their synthetic uses in the formation of biologically active compounds. Res. Chem. Intermed. 2016 42 2 771 811 10.1007/s11164‑015‑2055‑9
    [Google Scholar]
  3. Ushiki Y. Kawabe K. Yamamoto-Okada K. Uneuchi F. Asanuma Y. Yamaguchi C. Ohta H. Shibata T. Abe T. Okumura-Kitajima L. Kosai Y. Endo M. Otake K. Munetomo E. Takahashi T. Kakinuma H. Design, synthesis and biological evaluation of novel indole derivatives as gut-selective NaPi2b inhibitors. Bioorg. Med. Chem. 2022 66 116783 10.1016/j.bmc.2022.116783 35576656
    [Google Scholar]
  4. Jöst C. Nitsche C. Scholz T. Roux L. Klein C.D. Promiscuity and selectivity in covalent enzyme inhibition: A systematic study of electrophilic fragments. J. Med. Chem. 2014 57 18 7590 7599 10.1021/jm5006918 25148591
    [Google Scholar]
  5. Yuan W. Chen X. Liu N. Wen Y. Yang B. Andrei G. Snoeck R. Xiang Y. Wu Y. Jiang Z. Schols D. Zhang Z. Wu Q. Synthesis, anti-varicella-zoster virus and anti-cytomegalovirus activity of 4,5-disubstituted 1,2,3-(1H)-triazoles. Med. Chem. 2019 15 7 801 812 10.2174/1573406414666181109095239 30411688
    [Google Scholar]
  6. Modi P. Patel S. Chhabria M. Discovery of newer pyrazole derivatives with potential anti-tubercular activity via 3D-QSAR based pharmacophore modelling, virtual screening, molecular docking and molecular dynamics simulation studies. Mol. Divers. 2023 27 4 1547 1566 10.1007/s11030‑022‑10511‑8 35969333
    [Google Scholar]
  7. Trofimov B.A. Saliy I.V. Gotsko M.D. Sobenina L.N. Ushakov I.A. Bio-inspired functionalized pyrrole-pyridone ensembles: Synthesis on the platform of acylethynylpyrroles. Synthesis 2020 52 18 2698 2704 10.1055/s‑0040‑1707148
    [Google Scholar]
  8. Hovhannisyan A. Pham T.H. Bouvier D. Piroyan A. Dufau L. Qin L. Cheng Y. Melikyan G. Reboud-Ravaux M. Bouvier-Durand M. New C4- and C1-derivatives of furo[3,4-c]pyridine-3-ones and related compounds: Evidence for site-specific inhibition of the constitutive proteasome and its immunoisoform. Bioorg. Med. Chem. Lett. 2014 24 6 1571 1580 10.1016/j.bmcl.2014.01.072 24534487
    [Google Scholar]
  9. Li L. Ruan B. Zhang Z. Huang L. Xu C. Microwave-assisted synthesis of 2-aminothiophene derivatives via improved gewald reactions. Heterocycles 2021 102 10 2007 2018 10.3987/COM‑21‑14513
    [Google Scholar]
  10. Bae E.J. Jo H. Kim S.S. Shin D.S. Yang J.Y. Bae M.A. Jeong P. Park C.S. Ahn J.H. Novel thioxothiazolo[3,4- a ]quinazolin-5(4 H )-one derivatives as BK Ca channel activators for urinary incontinence. ACS Med. Chem. Lett. 2022 13 7 1052 1061 10.1021/acsmedchemlett.2c00070 35859863
    [Google Scholar]
  11. Pokhodylo N. Manko N. Finiuk N. Klyuchivska O. Matiychuk V. Obushak M. Stoika R. Primary discovery of 1-aryl-5-substituted-1H-1,2,3-triazole-4-carboxamides as promising antimicrobial agents. J. Mol. Struct. 2021 1246 131146 10.1016/j.molstruc.2021.131146
    [Google Scholar]
  12. Jooya A. Davoodnia A. Fattahi M. Tavakoli-Hoseini N. Rapid synthesis of N -Alkyl-2-imino-2 H -chromene-3-carboxamides catalyzed by a keplerate-type giant nanoporous isopolyoxomolybdate. Org. Prep. Proced. Int. 2018 50 6 565 574 10.1080/00304948.2018.1537732
    [Google Scholar]
  13. Kong L. Huang R. He H. Fan Y. Lin J. Yan S. Multi-component solvent-free cascade reaction of 2-cyanoacetamides: Regioselective synthesis of pyridin-2-ones bearing quaternary centers. Green Chem. 2020 22 1 256 264 10.1039/C9GC03692J
    [Google Scholar]
  14. Dotsenko V.V. Frolov K.A. Krivokolysko S.G. Polovinko V.V. Unexpected result in the reaction of 3-amino-3-thioxopropanamides with 2-anilinomethylene derivatives of 1,3-dicarbonyl compounds. synthesis of pyrimidine-5-carboxamide derivatives. Chem. Heterocycl. Compd. 2013 49 3 440 451 10.1007/s10593‑013‑1266‑5
    [Google Scholar]
  15. El Malah T. Abdel Mageid R.E. Shamroukh A.H. Review of the synthesis, reactions and pharmaceutical potential of pyrido[2,3-d]pyrimidine derivatives. Curr. Org. Chem. 2023 27 4 260 281 10.2174/1385272827666230410114551
    [Google Scholar]
  16. Anand A. Khanapurmath N. Kulkarni M.V. Guru Row T.N. Biheterocyclic coumarins: A simple yet versatile resource for futuristic design and applications in bio-molecular and material chemistry. Curr. Org. Chem. 2022 26 5 444 506 10.2174/1385272826666220301124149
    [Google Scholar]
  17. Khidre R.E. Mostafa M.S. Mukhrish Y.E. Salem M.A. Behalo M.S. Synthetic methods of 1H-pyrazolo[1,2-b]phthalazine derivatives. Curr. Org. Chem. 2023 26 22 2055 2069 10.2174/1385272827666230124145625
    [Google Scholar]
  18. Chaudhary A. Multicomponent approach for the sustainable syntheses of Pyrido[2,3-d]pyrimidine scaffold. Curr. Org. Chem. 2021 25 23 2856 2884 10.2174/1385272825666211117152900
    [Google Scholar]
  19. Tsuji S. Kudo U. Hatakeyama R. Shoda K. Nakamura S. Shimazawa M. Linagliptin decreased the tumor progression on glioblastoma model. Biochem. Biophys. Res. Commun. 2024 711 149897 10.1016/j.bbrc.2024.149897 38608433
    [Google Scholar]
  20. Shaik J.B. Palaka B.K. Penumala M. Kotapati K.V. Devineni S.R. Eadlapalli S. Darla M.M. Ampasala D.R. Vadde R. Amooru G.D. Synthesis, pharmacological assessment, molecular modeling and in silico studies of fused tricyclic coumarin derivatives as a new family of multifunctional anti-Alzheimer agents. Eur. J. Med. Chem. 2016 107 219 232 10.1016/j.ejmech.2015.10.046 26588065
    [Google Scholar]
  21. Mahía A. Peña-Díaz S. Navarro S. José Galano-Frutos J. Pallarés I. Pujols J. Díaz-de-Villegas M.D. Gálvez J.A. Ventura S. Sancho J. Design, synthesis and structure-activity evaluation of novel 2-pyridone-based inhibitors of α-synuclein aggregation with potentially improved BBB permeability. Bioorg. Chem. 2021 117 105472 10.1016/j.bioorg.2021.105472 34775206
    [Google Scholar]
  22. Liang X. Sun C. Li C. Yu H. Wei X. Liu X. Bao W. Shi Y. Sun X. Khamrakulov M. Yang C. Liu H. Identification of novel fused heteroaromatics-based MALT1 inhibitors by high-throughput screening to treat B cell lymphoma. J. Med. Chem. 2021 64 13 9217 9237 10.1021/acs.jmedchem.1c00466 34181850
    [Google Scholar]
  23. Mekky A.E.M. Sanad S.M.H. New Bis(pyrazolo[5,1‐ b ]quinazolines) and Bis(9 H ‐xanthenediones) linked to alkane cores: One‐pot synthesis, antibacterial screening, and SAR study. Chem. Biodivers. 2024 04 e202401700 10.1002/cbdv.202401700 39284770
    [Google Scholar]
  24. Ahmed M.S.M. Mekky A.E.M. Sanad S.M.H. Regioselective three-component synthesis and theoretical calculations of new alkane-linked bis(thiazol-2(3H)-imine) hybrids: A DFT-based FMO and local reactivity indices. J. Indian Chem. Soc. 2023 20 10 2527 2542 10.1007/s13738‑023‑02851‑5
    [Google Scholar]
  25. Ibrahim S.A. Fayed E.A. Rizk H.F. Desouky S.E. Ragab A. Hydrazonoyl bromide precursors as DHFR inhibitors for the synthesis of bis-thiazolyl pyrazole derivatives; Antimicrobial activities, antibiofilm, and drug combination studies against MRSA. Bioorg. Chem. 2021 116 105339 10.1016/j.bioorg.2021.105339 34530234
    [Google Scholar]
  26. Forezi da SM An update on the synthesis and applications of Bis (Naphthoquinones): An important class of molecules against infectious diseases and other conditions. Curr. Top. Med. Chem. 2021 21 1977 1998 10.2174/1568026621666210727165421
    [Google Scholar]
  27. Lima C.G. de Souza A.S. Pauli F.P. Ribeiro R.C.B. Functional group transformation in naphthoquinones: Strategies for the synthesis of mono-and Bis(Amino-1,4-naphthoquinones). Curr. Org. Chem. 2021 25 2156 2174 10.2174/1385272825666210811121450
    [Google Scholar]
  28. Sasidharan A.K. Mathew J. Achalkumar A.S. Mathews M. Synthesis and liquid crystalline properties of low molecular weight bis- chalcone compounds. Curr. Org. Synth. 2022 19 3 463 475 10.2174/1570179418666211006144308 34620065
    [Google Scholar]
  29. Mekky A.E.M. Sanad S.M.H. [3+2] cycloaddition synthesis of new piperazine‐linked bis(chromene) hybrids possessing pyrazole units as potential acetylcholinesterase inhibitors. Chem. Biodivers. 2023 20 4 e202200518 10.1002/cbdv.202200518 36988046
    [Google Scholar]
  30. Sanad S.M.H. Mekky A.E.M. Three-component regioselective synthesis and antibacterial evaluation of new arene-linked bis(pyrazolo[1,5- a ]pyrimidine) hybrids. Synth. Commun. 2023 53 9 658 672 10.1080/00397911.2023.2191854
    [Google Scholar]
  31. Panigrahi D. Subramaniyan V. Mani G. Synthesis and structural characterizations of Pd(II) complexes bearing the new hexahydropyrimidine and tetrahydropyrimidinium based bis(pyrazole) ligands with DFT studies. J. Mol. Struct. 2021 1231 129949 10.1016/j.molstruc.2021.129949
    [Google Scholar]
  32. Ahmed A.A.M. Mekky A.E.M. Elwahy A.H.M. Sanad S.M.H. Facile synthesis and characterization of novel benzo-fused macrocyclic dicarbonitriles and pyrazolo-fused macrocycles containing thiazole subunits. Synth. Commun. 2020 50 6 796 804 10.1080/00397911.2019.1689269
    [Google Scholar]
  33. Abbas A.A. Synthesis of novel macrocyclic di‐ and tetralactams and their corresponding C‐pivot lariat derivatives. ChemistrySelect 2023 8 18 e202204933 10.1002/slct.202204933
    [Google Scholar]
  34. Demir S. Erer H. Synthesis and characterization of new 2D coordination polymers based on mixed 1,1-cyclopentanediacetate and 1,2-bis((1H-imidazol-1-yl)methyl)benzene linkers. J. Mol. Struct. 2024 1295 136502 10.1016/j.molstruc.2023.136502
    [Google Scholar]
  35. Hu A. MacMillan S.N. Wilson J.J. Macrocyclic ligands with an unprecedented size-selectivity pattern for the lanthanide ions. J. Am. Chem. Soc. 2020 142 31 13500 13506 10.1021/jacs.0c05217 32697907
    [Google Scholar]
  36. Jiang M. Wu R. Liu D. Wang X. Utilizing Ni(II) complex for metal drug-gel particles in cervical cancer treatment and designing novel drugs through machine learning methods. Sci. Rep. 2024 14 1 5421 10.1038/s41598‑024‑55897‑7 38443412
    [Google Scholar]
  37. Mishra P. Sethi P. Kumar S. Rathi P. Umar A. Kumar R. Chaudhary S. Alkhanjaf A.A.M. Ibrahim A.A. Baskoutas S. Synthesis and biomedical applications of macrocyclic complexes. J. Mol. Struct. 2024 1317 139098 10.1016/j.molstruc.2024.139098
    [Google Scholar]
  38. Mekky A.E.M. Abdelbaath R.A. Abdelbaath R.A. Marie A.E. Arafa M.A. Halim E.E. Sanad S.M.H. New arene and/or heteroarene‐linked 1,3,4‐oxadiazoles: Synthesis of potential methicillin‐resistant Staphylococcus aureus and vancomycin‐resistant enterococcus inhibitors. ChemistrySelect 2024 9 36 e202403359 10.1002/slct.202403359
    [Google Scholar]
  39. Sanad S.M.H. Mekky A.E.M. Potential MRSA inhibitory activity of some new benzofuran-pyrazolo[1,5- a ]pyrimidine hybrids attached to arene units via methylene or azo linkage. Synth. Commun. 2024 54 21 1857 1870 10.1080/00397911.2024.2409875
    [Google Scholar]
  40. Elneairy M.A.A. Youssef E.G.N. Ebrahim S.A.A. Mohammad N.E.M. Abd El-Rahman N.M.S. Elhewaty A.S.M. Sanad S.M.H. Mekky A.E.M. MRSA inhibitory activity of some new pyrazolo[1,5‐ a ]pyrimidines linked to arene and/or furan or thiophene units. Chem. Biodivers. 2024 16 e202402031 10.1002/cbdv.202402031 39284766
    [Google Scholar]
  41. Sanad S.M.H. 2,3-Diaminonaphthalene-1,4-dione: Versatile precursor for the synthesis of molecular systems. Synth. Commun. 2024 25 1 24 10.1080/00397911.2024.2435467
    [Google Scholar]
  42. Ahmed A.A.M. Mekky A.E.M. Sanad S.M.H. Synthesis of new bis(pyrazolo[1,5-a]pyrimidines) linked to different spacers with potential MurB inhibitory activity utilizing 1H-pyrazole-3,5-diamines. Synth. Commun. Accept 2024 06 10.1080/00397911.2024.2428653
    [Google Scholar]
  43. Gazit A. Osherov N. Gilon C. Levitzki A. Tyrphostins. 6. Dimeric benzylidenemalononitrile tyrophostins: potent inhibitors of EGF receptor tyrosine kinase in vitro. J. Med. Chem. 1996 39 25 4905 4911 10.1021/jm960225d 8960549
    [Google Scholar]
  44. Peng Z. Maxwell D.S. Sun D. Bhanu Prasad B.A. Schuber P.T. Jr Pal A. Ying Y. Han D. Gao L. Wang S. Levitzki A. Kapuria V. Talpaz M. Young M. Showalter H.D. Donato N.J. Bornmann W.G. Degrasyn-like symmetrical compounds: Possible therapeutic agents for multiple myeloma (MM-I). Bioorg. Med. Chem. 2014 22 4 1450 1458 10.1016/j.bmc.2013.12.048 24457091
    [Google Scholar]
  45. Cheikh N. Bar N. Choukchou-Braham N. Mostefa-Kara B. Lohier J.F. Sopkova J. Villemin D. Efficient synthesis of new butenolides by subsequent reactions: Application for the synthesis of original iminolactones, bis-iminolactones and bis-lactones. Tetrahedron 2011 67 8 1540 1551 10.1016/j.tet.2010.12.062
    [Google Scholar]
  46. Cheadle C. Gerasimchuk N. Barnes C.L. Tyukhtenko S.I. Silchenko S. The first bis-cyanoxime: Synthesis and properties of a new versatile and accessible polydentate bifunctional building block for coordination and supramolecular chemistry. Dalton Trans. 2013 42 14 4931 4946 10.1039/c2dt31924a 23385567
    [Google Scholar]
  47. Husseiny E.M. Menofy E. Galal N. El-Sebaey S. 1,8-Diaminonaphthalene-derived pharmacophore as potent anti-MRSA with dual DNA gyrase and topoisomerase IV inhibition. Egypt. J. Chem. 2022 65 1 17 10.21608/ejchem.2021.104410.4824
    [Google Scholar]
  48. Metwally N.H. Abdelrazek F.M. Jaafar M.T. Synthesis and antimicrobial activity of some novel substituted bis‐pyridone, pyrazole, and thiazole derivatives. J. Heterocycl. Chem. 2015 52 2 358 365 10.1002/jhet.2043
    [Google Scholar]
  49. Sohn D.H. Han E. Cho S.J. Kang J. Phosphinate selective hosts and importance of C H hydrogen bonding for affinity modulation toward anion guests. Tetrahedron Lett. 2018 59 18 1728 1732 10.1016/j.tetlet.2018.03.066
    [Google Scholar]
  50. Girgis A.S. Abbas A.A. Synthesis of new benzo-fused macrocycle diamides. J. Chem. Res. 2000 2000 10 460 461 10.3184/030823400103165897
    [Google Scholar]
  51. Abbas A.A. Girgis A.S. A convenient synthesis of thiamacrocyclic dilactams. Heteroatom Chem. 2007 18 3 249 254 10.1002/hc.20292
    [Google Scholar]
  52. Sanad S.M.H. Elwahy A.H.M. Abdelhamid I.A. Bis(2-cyanoacetamides): Versatile precursors for bis(dihydropyridine-3,5-dicarbonitriles). ARKIVOC 2018 2018 7 39 49 10.24820/ark.5550190.p010.683
    [Google Scholar]
  53. Hebishy A.M.S. Abdelhamid I.A. Elwahy A.H.M. Synthesis of novel bis(dihydropyridine) and terpyridine derivatives. ARKIVOC 2018 2018 5 109 123 10.24820/ark.5550190.p010.498
    [Google Scholar]
  54. Hill T.A. Sakoff J.A. Robinson P.J. McCluskey A. Parallel solution-phase synthesis of targeted tyrphostin libraries with anticancer activity. Aust. J. Chem. 2005 58 2 94 103 10.1071/CH04143
    [Google Scholar]
  55. Ahmed A.A.M. Mekky A.E.M. Sanad S.M.H. Effective synthesis of new benzo‐fused macrocyclic and thiamacrocyclic dilactams and related pyrazolo‐fused macrocycles. J. Heterocycl. Chem. 2022 59 2 286 296 10.1002/jhet.4383
    [Google Scholar]
  56. Odell L.R. Robertson M.J. Young K.A. McGeachie A.B. Quan A. Robinson P.J. McCluskey A. Prodrugs of the archetypal dynamin inhibitor Bis‐T‐22. ChemMedChem 2022 17 24 e202200400 10.1002/cmdc.202200400 36351775
    [Google Scholar]
  57. Mekky A.E.M. Ahmed A.A.M. Elwahy A.H.M. An efficient synthesis of novel benzo‐fused macrocyclic dilactams. Helv. Chim. Acta 2013 96 7 1290 1297 10.1002/hlca.201200529
    [Google Scholar]
  58. Kolotilov S.V. Schollmeyer D. Thompson L.K. Golub V. Addison A.W. Pavlishchuk V.V. Synthesis, structure and magnetic properties of oligometallic systems derived from di- and trinuclear copper(ii) amido-oximate complexes. Dalton Trans. 2008 2008 22 3007 3014 10.1039/b802822b 18493637
    [Google Scholar]
  59. Ali G.A.M.E.H. Helal M.H. Mohamed Y.A. Ali A.A. Ammar Y.A. Synthesis, characterisation and antimicrobial activity of thiazole, bisthiazole, pyridone and bispyridone derivatives. J. Chem. Res. 2010 34 8 459 464 10.3184/030823410X12812857779516
    [Google Scholar]
  60. Kheder N.A. Synthesis of some novel bis(pyrazole), bis(pyridine) and bis(pyrazolo[5,1-c]-1,2,4-triazine derivatives. Heterocycles 2009 78 1815 1822 10.3987/COM‑09‑11676
    [Google Scholar]
  61. Alexandre C. Melikian G. Rouessac F. Synthesis and reactivity of bis -lactamic compounds. Synth. Commun. 1997 27 11 1919 1925 10.1080/00397919708006793
    [Google Scholar]
  62. Avetisyan A.A. Karapetyan L.V. Synthesis and chemical transformations of bis-2-imino-2,5-dihydrofurans. Chem. Heterocycl. Compd. 2013 48 11 1613 1620 10.1007/s10593‑013‑1182‑8
    [Google Scholar]
  63. Hebishy A.M.S. Elgemeie G.H. Elwahy A.H.M. Novel Bis(2‐cyanoketene‐ S, S ‐/ S, N ‐acetals): Versatile precursors for novel Bis(aminopyrazole) derivatives. J. Heterocycl. Chem. 2019 56 5 1581 1587 10.1002/jhet.3536
    [Google Scholar]
  64. El-Sayed E.H. Fadda A.A. Synthesis and antimicrobial activity of some novel bis polyfunctional pyridine, pyran, and thiazole derivatives. J. Heterocycl. Chem. 2018 55 10 2251 2260 10.1002/jhet.3276
    [Google Scholar]
  65. Filimonov V.O. Dianova L.N. Beryozkina T.V. Mazur D. Beliaev N.A. Volkova N.N. Ilkin V.G. Dehaen W. Lebedev A.T. Bakulev V.A. Water/Alkali-catalyzed reactions of azides with 2-cyanothioacetamides. eco-friendly synthesis of monocyclic and bicyclic 1,2,3-thiadiazole-4-carbimidamides and 5-amino-1,2,3-triazole-4-carbothioamides. J. Org. Chem. 2019 84 21 13430 13446 10.1021/acs.joc.9b01599 31547663
    [Google Scholar]
  66. Abdelmoniem A.M. Salaheldin T.A. Abdelhamid I.A. Elwahy A.H.M. New Bis(dihydropyridine‐3,5‐dicarbonitrile) derivatives: Green synthesis and cytotoxic activity evaluation. J. Heterocycl. Chem. 2017 54 5 2670 2677 10.1002/jhet.2867
    [Google Scholar]
  67. Zitzler-Kunkel A. Lenze M.R. Meerholz K. Würthner F. Enhanced photocurrent generation by folding-driven H-aggregate formation. Chem. Sci. 2013 4 5 2071 2075 10.1039/c3sc50263e
    [Google Scholar]
  68. Zitzler-Kunkel A. Kirchner E. Bialas D. Simon C. Würthner F. Spacer‐modulated differentiation between self‐assembly and folding pathways for bichromophoric merocyanine dyes. Chemistry 2015 21 42 14851 14861 10.1002/chem.201502434 26346411
    [Google Scholar]
  69. Sanad S.M.H. Mekky A.E.M. Piperazine‐mediated tandem synthesis of bis(thieno[2,3‐ b ]pyridines): Versatile precursors for related fused [1,2,4]triazolo[4,3‐ a ]pyrimidines. J. Heterocycl. Chem. 2020 57 8 3142 3152 10.1002/jhet.4021
    [Google Scholar]
  70. Refat H.M. Fadda A.A. Kamal S. Synthesis and antitumor evaluation of some new biscarboxamidocoumarin and chromene derivatives. J. Indian Chem. Soc. 2015 12 5 845 854 10.1007/s13738‑014‑0547‑y
    [Google Scholar]
  71. Wang K. Herdtweck E. Dömling A. One-pot synthesis of 2-amino-indole-3-carboxamide and analogous. ACS Comb. Sci. 2011 13 2 140 146 10.1021/co100040z 21395342
    [Google Scholar]
  72. Hill T.A. Mariana A. Gordon C.P. Odell L.R. Robertson M.J. McGeachie A.B. Chau N. Daniel J.A. Gorgani N.N. Robinson P.J. McCluskey A. Iminochromene inhibitors of dynamins I and II GTPase activity and endocytosis. J. Med. Chem. 2010 53 10 4094 4102 10.1021/jm100119c 20426422
    [Google Scholar]
  73. Areias F. Costa M. Castro M. Brea J. Gregori-Puigjané E. Proença M.F. Mestres J. Loza M.I. New chromene scaffolds for adenosine A2A receptors: Synthesis, pharmacology and structure–activity relationships. Eur. J. Med. Chem. 2012 54 303 310 10.1016/j.ejmech.2012.05.009 22677030
    [Google Scholar]
  74. Shklyaev V.S. Aleksandrov B.B. Mikhailovskii A.G. Vakhrin M.I. Synthesis of enaminoamides of the 1,2,3,4-tetrahydroisoquinoline series. Chem. Heterocycl. Compd. 1989 25 9 1038 1041 10.1007/BF00487305
    [Google Scholar]
  75. Mikhailovskii A.G. Lichtenshtein E.S. Pershina N.N. Kolotyrkina N.G. Synthesis of Bis-[3,3-dialkyl-3,4-dihydroisoquinolin-1(2H)-ylidene]acetamides by the ritter reaction and their properties. Russ. J. Org. Chem. 2022 58 1 65 69 10.1134/S1070428022010080
    [Google Scholar]
  76. Gouda M.A. Synthesis and antioxidant evaluation of some new pyridopyrazolotriazine derivatives. J. Heterocycl. Chem. 2015 52 4 990 998 10.1002/jhet.2045
    [Google Scholar]
  77. Mekky A.E.M. Elwahy A.H.M. Synthesis of novel benzo‐substituted macrocyclic ligands containing thienothiophene subunits. J. Heterocycl. Chem. 2014 51 S1 E34 E41 10.1002/jhet.2012
    [Google Scholar]
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