A versatile approach for one-pot synthesis of hybridized quinolines linked to fused N-containing heterocycles in water

Younus HA, Al-Rashida M, Hameed A, Uroos M, Salar U, Rana S, Khan KM (2021) Multicomponent reactions (MCR) in medicinal chemistry: a patent review (2010–2020). Expert Opin Ther Pat 31(3):267–289 Calvo-Flores FG, Mingorance-Sánchez C (2021) Deep eutectic solvents and multicomponent reactions: two convergent items to green chemistry strategies. ChemistryOpen 10(8):815–829 Pulikkal Veettil S, Pookkandam Parambil S, Van Hoof M, Dehaen W (2021) A Multicomponent approach toward angularly fused/linear bitriazoles: a cascade cornforth rearrangement and triazolization. J Org Chem 86(5):4346–4354 Sharghi H, Aberi M, Doroodmand MM, Shiri P (2017) Chromium (III)-salen complex nanoparticles on AlPO4: as an efficient heterogeneous and reusable nanocatalyst for mild synthesis of highly functionalized piperidines, 2-arylbenzimidazoles, and 2-arylbenzothiazoles. J Iran Chem Soc 14(7):1557–1573 Hu Q-Q, Gao Y-T, Sun J-C, Gao J-J, Mu H-X, Li Y-M, Zheng Y-N, Yang K-R, Zhu Y-P (2021) Iodine-imine synergistic promoted povarov-type multicomponent reaction for the synthesis of 2, 2′-biquinolines and their application to a copper/ligand catalytic system. Org Lett 23(22):9000–9005 Yadav R, Parvin T (2021) Multicomponent synthesis of styryl linked benzo [h] pyrazolo [3, 4-b] quinoline-5, 6 (10 H)-diones by liquid assisted grinding. New J Chem 45(23):10388–10395 Khalili D, Evazi R, Neshat A, Aboonajmi J (2021) Copper (I) complex of dihydro bis (2-mercapto benzimidazolyl) borate as an efficient homogeneous catalyst for the synthesis of 2H-indazoles and 5-substituted 1H-tetrazoles. ChemistrySelect 6(4):746–753 Shanker G, Srinatha M, Kumari DS, Ranjitha B, Alaasar M (2022) Novel green synthetic approach for liquid crystalline materials using multi-component reactions. J Mol Liq 346:118244 Wang X, Chen S, Cui H, He Y, Zhao C (2022) Three-step synthetic procedure to prepare dolutegravir, cabotegravir, and bictegravir. Green Chem Lett Rev 15(2):311–318 Sharghi H, Aboonajmi J, Aberi M (2020) One-pot multicomponent reaction of catechols, ammonium acetate, and aldehydes for the synthesis of benzoxazole derivatives using the Fe (III)–Salen complex. J Org Chem 85(10):6567–6577 Heravi MM, Zadsirjan V, Dehghani M, Ahmadi T (2018) Towards click chemistry: multicomponent reactions via combinations of name reactions. Tetrahedron 74(27):3391–3457 Gapanenok D, Makhmet A, Peshkov AA, Smirnova D, Amire N, Peshkov VA, Spiridonova D, Dar’in D, Balalaie S, Krasavin M (2022) Multicomponent assembly of trisubstituted imidazoles and their photochemical cyclization into fused polyheterocyclic scaffolds. J Org Chem. https://doi.org/10.1021/acs.joc.2c00475 Hosseini-Sarvari M, Roosta A (2014) Synthesis of 2-amino-4H-chromen-4-yl phosphonats via CP bond formation catalyzed by nano-rods ZnO under solvent-free condition. Comb Chem High Throughput Screen 17(1):47–52 Sharghi H, Khalifeh R, Doroodmand MM (2009) Copper nanoparticles on charcoal for multicomponent catalytic synthesis of 1, 2, 3-triazole derivatives from benzyl halides or alkyl halides, terminal alkynes and sodium azide in water as a “Green” solvent. Adv Synth Catal 351(1–2):207–218 Sharghi H, Aboonajmi J, Aberi M, Shiri P (2018) Heterogeneous AlPO4 (SO3H) nanosheets: novel catalyst for the multi-component synthesis of quinazolinones and highly functionalized piperidines. J Iran Chem Soc 15(5):1107–1118 Zhou F, Hearne Z, Li C-J (2019) Water—the greenest solvent overall. Curr Opin Green Sustain Chem 18:118–123 Sheldon RA (2019) The greening of solvents: towards sustainable organic synthesis. Curr Opin Green Sustain Chem 18:13–19 Rezaei F, Amrollahi MA, Khalifeh R (2019) Design and synthesis of Fe3O4@ SiO2/aza-crown ether-Cu (II) as a novel and highly efficient magnetic nanocomposite catalyst for the synthesis of 1, 2, 3-triazoles, 1-substituted 1H-tetrazoles and 5-substituted 1H-tetrazoles in green solvents. Inorg Chim Acta 489:8–18 Lindström UM (2002) Stereoselective organic reactions in water. Chem Rev 102(8):2751–2772 Tekin K, Hao N, Karagoz S, Ragauskas AJ (2018) Ethanol: a promising green solvent for the deconstruction of lignocellulose. Chemsuschem 11(20):3559–3575 Rezvanian A, Amoozadkhalili F, Roosta A (2021) Sequential four-component protocol for the synthesis of pyrido [1, 2-a] pyrimidin-6-one derivatives in water. Chem Pap 75(6):2417–2424 Rezvanian A, Kuhzadeh P, Roosta A (2021) Synthesis of novel 1, 3-cyclohexadiene derivatives bearing 2-oxo-quinoline moiety via a 4-CR strategy. ChemistrySelect 6(45):12965–12969 Weyesa A, Mulugeta E (2020) Recent advances in the synthesis of biologically and pharmaceutically active quinoline and its analogues: a review. RSC Adv 10(35):20784–20793 Marella A, Tanwar OP, Saha R, Ali MR, Srivastava S, Akhter M, Shaquiquzzaman M, Alam MM (2013) Quinoline: a versatile heterocyclic. Saudi Pharm J 21(1):1–12 Matada BS, Pattanashettar R, Yernale NG (2021) A comprehensive review on the biological interest of quinoline and its derivatives. Bioorg Med Chem 32:115973 Persoons L, Vanderlinden E, Vangeel L, Wang X, Do NDT, Foo S-YC, Leyssen P, Neyts J, Jochmans D, Schols D (2021) Broad spectrum anti-coronavirus activity of a series of anti-malaria quinoline analogues. Antivir Res 193:105127 Alizadeh A, Rezaiyehraad R, Roosta A, Halvagar MR (2019) Synthesis of 1H-thiopyrano [4, 3-c] quinoline scaffold via one-pot three-component cyclization. ChemistrySelect 4(41):12049–12052 Alizadeh A, Roosta A, Asalemi KAA (2018) One-pot three-component synthesis of 2 H-thiopyrano [2, 3-b] quinoline-2, 3-dicarboxylates from 2-mercaptoquinoline-3-carbaldehydes, dialkyl acetylenedicarboxylates and Ph3P. J Sulfur Chem 39(4):435–442 Prajapati SM, Patel KD, Vekariya RH, Panchal SN, Patel HD (2014) Recent advances in the synthesis of quinolines: a review. RSC Adv 4(47):24463–24476 Shiri P, Ramezanpour S, Amani AM, Dehaen W (2022) A patent review on efficient strategies for the total synthesis of pazopanib, regorafenib and lenvatinib as novel anti-angiogenesis receptor tyrosine kinase inhibitors for cancer therapy. Mol Divers. https://doi.org/10.1007/s11030-022-10406-8 Zheng T, Rouhanifard SH, Jalloh AS, Wu P (2012) Click triazoles for bioconjugation. In: Click triazoles. Springer, Berlin, pp 163–183 Agalave SG, Maujan SR, Pore VS (2011) Click chemistry: 1, 2, 3-triazoles as pharmacophores. Chemistry—Asian J 6(10):2696–2718 Fan YL, Ke X, Liu M (2018) Coumarin–triazole hybrids and their biological activities. J Heterocycl Chem 55(4):791–802 Shiri P (2021) Novel hybrid molecules based on triazole-β-lactam as potential biological agents. Mini Rev Med Chem 21(5):536–553 Kaur R, Sharma P, Gupta GK, Ntie-Kang F, Kumar D (2020) Structure-activity-relationship and mechanistic insights for anti-HIV natural products. Molecules 25(9):2070 Rezvanian A (2016) An expedient synthesis strategy to the 1, 4-dihydropyridines and pyrido [1, 2-a] quinoxalines: iodine catalyzed one-pot four-component domino reactions. Tetrahedron 72(41):6428–6435 Rezvanian A (2015) Iodine catalyzed mild 4CR protocol for synthesis of tetrahydroimidazo [1, 2-a] pyridines: cascade construction of multiple C-C and C–hetero bonds. Tetrahedron 71(29):4752–4756 Rezvanian A, Heravi MM, Shaabani Z, Tajbakhsh M (2017) Five-component synthesis of dihydropyridines based on diketene. Tetrahedron 73(15):2009–2013 Alizadeh A, Rezvanian A, Zhu LG (2012) Synthesis of heterocyclic [3.3.3] propellanes via a sequential four-component reaction. J Org Chem 77(9):4385–4390 Rezvanian A, Moradi F, Zadsirjan V, Mohammadnejad M, Heravi MM (2020) Cascade process for direct synthesis of indeno [1, 2-b] furans and indeno [1, 2-b] pyrroles from diketene and ninhydrin. Mol Divers 24(4):1313–1325 Rezvanian A, Alinaghian F, Heravi MM (2018) Metal-free assemblage of four C−N and two C−C bonds via a cascade five component diastereoselective synthesis of pyrido [1, 2-a] pyrimidines. ChemistrySelect 3(41):11565–11568 Rezvanian A, Mahmoodi F, Zadsirjan V, Salimi M, Heravi MM (2020) Efficient and uncatalyzed synthesis of highly functionalized new symmetrical indeno [1, 2-b] pyrroles via a one-pot four-component reaction. ChemistrySelect 5(12):3503–3507 Rezvanian A, Babashah M, Anafcheh M (2019) A novel pseudo six-component synthesis of functionalized pyrazoles in ethanol by cascade reaction. Mol Divers 23(4):875–883 Rezvanian A, Noorakhtar F, Ziarani GM, Mahajer F (2020) Quinoline conjugated imidazopyridine and pyridopyrimidine synthesis in water as highly selective fluoride sensors via a catalyst-free four-component reaction. Monatshefte für Chemie-Chem Mon 151(10):1581–1589 Talaei B, Heravi MM, Oskooie HA, Rezvanian A (2018) An approach to the diastereoselective synthesis of cyclohexane-1, 3-dicarboxamide derivatives via a pseudo five-component reaction based on diketene. Synlett 29(02):225–229 Rezvanian A, Khodadadi B, Tafreshi S (2022) Use of dialkyl acetylenedicarboxylates in the multicomponent synthesis of heterocyclic structures. ChemistrySelect 7(34):3503–3507 Fan Y, Liu S, Chen N, Shao X, Xu X, Li Z (2015) Oxidation strategy for the synthesis of regioisomeric spiroisobenzofuranopyrroles: facile entries to spiro [isobenzofuran-1, 2′-pyrrole] and spiro [isobenzofuran-1, 3′-pyrrole] derivatives. Synlett 26(03):393–403 Baruah B, Bhuyan PJ (2009) Synthesis of some complex pyrano[2,3-b]- and pyrido[2,3-b]quinolines from simple acetanilides via intramolecular domino hetero Diels-Alder reactions of 1-oxa-1,3-butadienes in aqueous medium. Tetrahedron 65:7099