How to cite this paper
Vaskevych, A., Savinchuk, N & Vov, M. (2025). Synthesis of pyrrolo(pyrido)[1,2-a]quinazolinones and their benzoannulated analogues: An overview.Current Chemistry Letters, 14(3), 507-532.
Refrences
1. Alagarsamy, V., Chitra, K., Saravanan, G., Solomon, V. R., Sulthana, M. T., Narendhar, B. (2018) An overview of quinazolines: Pharmacological significance and recent developments. Eur. J. Med. Chem., 151, 628–685. https://doi.org/10.1016/j.ejmech.2018.03.076
2. Alagarsamy, V., Raja Solomon, V., Dhanabal, K. (2007) Synthesis and pharmacological evaluation of some 3-phenyl-2-substituted-3H-quinazolin-4-one as analgesic, anti-inflammatory agents. Bioorg. Med. Chem., 15(1), 235–241. https://doi.org/10.1016/j.bmc.2006.09.065
3. Ammar, Y. A., Bondock, S., El-Sehmi, A. G., El Gaby, M. S. A., Fouda, A. M. (2011) Facile and convenient synthesis of pyrimidine, 4H-3,1-benzoxazin-4-one, pyrazolo[5,1-b]quinazoline, pyrido[1,2-a]quinazoline, and chromeno[3',4':4,5]pyrido[1,2-a]quinazoline derivatives. Turk. J. Chem., 35(6), 893–903. https://doi.org/10.3906/kim-1104-54
4. Badigenchala, S., Sekar, G. (2017) NIS mediated cross-coupling of C(sp2)–H and N–H bonds: A transition-metal-free approach toward indolo[1,2-a]quinazolinones. J. Org. Chem., 82(14), 7657–7665. https://doi.org/10.1021/acs.joc.7b01080
5. Bera, S. K., Mal, P. (2022) Regiodivergent C–N coupling of quinazolinones controlled by the dipole moments of tautomers. Org. Lett., 24(17), 3144-3148. https://doi.org/10.1021/acs.orglett.2c00847
6. Boomhoff, M., Ukis, R.;, Schneider, C. A (2015) Highly stereocontrolled, one-pot approach toward pyrrolobenzoxazinones and pyrroloquinazolinones through a Lewis acid-catalyzed [3+2]-cycloannulation process. J. Org. Chem., 80(16), 8236–8244. https://doi.org/10.1021/acs.joc.5b01293
7. Brown, C. E., Kong, T., Britten, J. F., Werstiuk, N. H., McNulty, J., D’Aiuto, L., Nimgaonkar, V. L. (2018) Asymmetric entry into 10b-aza-analogues of Amaryllidaceae alkaloids reveals a pronounced electronic effect on antiviral activity. ACS Omega, 3(9), 11469–11476. https://doi.org/10.1021/acsomega.8b01987
8. Bunce, R. A., Nammalwar, B. (2011) New conditions for synthesis of (±)-2-monosubstituted and (±)-2,2-disubstituted 2,3-dihydro-4(1H)-quinazolinones from 2-nitro- and 2-aminobenzamide. J. Heterocycl. Chem., 48(5), 991–997. https://doi.org/10.1002/jhet.672
9. Chechani, B., Kumar, M., Yadav, D. K., Sharma, S., Kumari, N. (2024) Schizocommunin-inspired heterocyclic hybrid molecules. Chem. Heterocycl. Comp., 60, 280–288. https://doi.org/10.1007/s10593-024-03334-y
10. Cho, J.-Y., Bae, S.-H., Kim, H.-K., Lee, M.-L., Choi, Y.-S., Jin, B.-R., Moon, J.-H. (2015) New quinolinone alkaloids from Chestnut (Castanea crenata sieb) honey. J. Agric. Food Chem., 63(13), 3587–3592. https://doi.org/10.1021/acs.jafc.5b01027
11. Darras, F. H., Kling, B., Heilmann, J., Decker, M. (2012) Neuroprotective Tri- and Tetracyclic BChE Inhibitors Releasing Reversible Inhibitors upon Carbamate Transfer. ACS Med. Chem. Lett., 3(11), 914–919. https://doi.org/10.1021/ml3001825
12. Dumitrascu, F., Georgescu, F., Georgescu, E, Caira, M. R. (2019) Chapter Three – Pyrroloquinolines, imidazoquinolines, and pyrroloquinazolines with a bridgehead nitrogen. Adv. Heterocycl. Chem., 129, 155–244. https://doi.org/10.1016/bs.aihch.2019.01.004
13. Dumitrascu, F., Popa, M. M. (2014) Pyrrolo[1,2-a]quinazolines. Synthesis and biological properties. ARKIVOC, (i), 428–452. https://doi.org/10.3998/ark.5550190.p008.699
14. Dunn, A. D., Kinnear, K. I. (1986) New reactions of deoxyvasicinone. Part 4. J. Heterocycl. Chem., 23(1), 53–57. https://doi.org/10.1002/jhet.5570230111
15. Elbouhi, M., Tabti, K., Ouabane, M., Alaqarbeh, M., Elkamel, K., Lakhlifi, T., Sbai, A., Bouachrine, M. (2024) A computational exploration of the antioxidant potential of conjugated quinazolinone Schiff bases. Chem. Heterocycl. Comp., 60, 627–638. https://doi.org/10.1007/s10593-025-03386-8
16. Fantin, G., Fogagnolo, M., Medici,A., Pedrini, P. (1993) Tetrahydropyrido[2,1-b]quinazolin-11-ones and tetrahydropyrido[l,2-a]quinazolin-6-ones via thermal cyclization of 2-substituted 4(3H)-quinazolinones. J. Org. Chem., 58, 741–743. https://doi.org/10.1021/jo00055a032
17. Feng, E., Zhou, Y., Zhang, D., Zhang, L., Sun, H., Jiang, H., Liu, H. (2010) Gold(I)-catalyzed tandem transformation: A simple approach for the synthesis of pyrrolo/pyrido[2,1-a][1,3]benzoxazinones and pyrrolo/pyrido[2,1-a]quinazolinones. J. Org. Chem., 75(10), 3274–3282. https://doi.org/10.1021/jo100228u
18. Ferraris, D.V. (2010) Evolution of poly(ADP-ribose) polymerase-1 (PARP-1) inhibitors. From concept to clinic. J. Med. Chem., 53, 4561-4584. https://doi.org/10.1021/jm100012m
19. Gogoi, K., Bora, B. R., Borah, G., Sarma, B., Gogoi, S. (2021) Synthesis of quaternary carbon-centered indolo[1,2-a]quinazolinones and indazolo[1,2-a]indazolones via C–H functionalization. Chem. Commun., 57(11), 1388–1391. https://doi.org/10.1039/d0cc07419e
20. Guda, R., Korra, R., Balaji, S., Palabindela, R., Eerla, R., Lingabathula, H., Kasula, M. (2017) Design, synthesis and biological evaluation of 8-substituted-6-hydrazonoindolo[2,1-b]quinazolin-12(6H)-one scaffolds as potential cytotoxic agents: IDO-1 targeting molecular docking studies. Bioorg. Med. Chem. Lett., 27(20), 4741–4748. https://doi.org/10.1016/j.bmcl.2017.08
21. He, D., Wang, M., Zhao, S., Shu, Y., Zeng, H., Xiao, C., Lu, C., Liu, Y. (2017) Pharmaceutical prospects of naturally occurring quinazolinone and its derivatives. Fitoterapia., 119, 136–149. https://doi.org/10.1016/j.fitote.2017.05.001
22. Hekal, M. H., Abu El-Azm, F. S. M. (2017) Efficient MW-assisted synthesis of some new isoquinolinone derivatives with in vitro antitumor activity. J. Heterocycl. Chem., 54(6), 3056–3064. https://doi.org/10.1002/jhet.2916
23. Henning, H. G., Haber H. (1988) Heterocyclensynthesen mit 5-Phenyl-isoxazoliumsalzen, 3. Mitt.: Synthese von Pyrrolo[1,2-a]chinazolin-5-onen. Monatsh. Chem., 119, 1405–1414. https://doi.org/10.1007/BF00810284
24. Hu, X., Wang, J., Jiang, L., Liu, X., Ge, Q., Wang, Q., Qi, X., Wu, Y. (2024) Rutaecarpine protects podocytes in diabetic kidney disease by targeting VEGFR2/NLRP3-mediated pyroptosis. Int. Immunopharmacol., 130(30), 111790. https://doi.org/10.1016/j.intimp.2024.111790
25. Huang, T., Wang, T., Shi, Y., Chen, J., Guo, X., Lai, R., Wu, Y. (2021) Rh(III)-catalyzed C–H olefination cascades to divergently construct diverse polyheterocycles by tuning manipulations of directing groups. Org. Lett., 23(5), 1548–1553. https://doi.org/10.1021/acs.orglett.0c04155
26. Iminov, R. T., Tverdokhlebov, A. V., Tolmachev, A. A., Volovenko, Y. M., Shishkina, S. V., Shishkin, O. V. (2009) Synthesis of structurally constrained 4-quinazolinone derivatives with a tetrahedral C-2 atom present in three rings. Tetrahedron, 65(41), 8582–8586. https://doi.org/10.1016/j.tet.2009.07.059
27. Jaouen, J., Bailly, C. (2025) Alkaloids from Mackinlaya species and synthetic mackinazolinone derivatives: An overview. Bioorg. Med. Chem., 117, 118018. https://doi.org/10.1016/j.bmc.2024.118018
28. Jia, X., Li, P., Liu, X., Lin, J., Chu, Y., Yu, J., Zhao, F. (2019) Green and facile assembly of diverse fused N-heterocycles using Gold-catalyzed cascade reactions in water. Molecules, 24(5), 988. https://doi.org/10.3390/molecules24050988
29. Jones, A. M., Lebl, T., Patterson, S., van Mourik, T., Früchtl, H. A., Philp, D., Westwood, N. J. (2009) Parallel synthesis and spectroscopic analysis of a collection of heterocycles based on the diazabenz[e]aceanthrylene core structure. Tetrahedron, 65(2), 563–578. https://doi.org/10.1016/j.tet.2008.10.049
30. Kazemi, S. S., Keivanloo, A., Nasr-Isfahani, H., Bamoniri, A. (2016) Synthesis of novel 1,5-disubstituted pyrrolo[1,2-a]quinazolines and their evaluation for anti-bacterial and anti-oxidant activities. RSC Advances, 6(95), 92663–92669. https://doi.org/10.1039/c6ra21219k
31. Khan, I., Ibrar, A., Ahmed, W., Saeed, A. (2015) Synthetic approaches, functionalization and therapeutic potential of quinazoline and quinazolinone skeletons: The advances continue. Eur. J. Med. Chem., 90, 124–169. https://doi.org/10.1016/j.ejmech.2014.10.084
32. Kisel, V. M., Kostyrko, E. O., Kovtunenko, V. A. (2002) Condensed isoquinolines. 13. Synthesis of 1,2,3,4-tetrahydrospiro[isoquinoline-4,1'-cyclopentane]-3-imines and condensed spirocyclic systems based on them. Chem. Heterocycl. Compd., 38, 940–946. https://doi.org/10.1023/A:1020969413371
33. Kisel, V. M., Kostyrko, E. O., Platonov, M. O., Kovtunenko, V. A. (2002) Condensed isoquinolines. 12. Synthesis of novel heterocyclic systems containing a partially hydrogenated spiro[isoquinoline-4,4'-(2H)-pyran] fragment. Chem. Heterocycl. Compd., 38(3), 300–305. https://doi.org/10.1023/A:1015683219884
34. Kotipalli, T., Kavala, V., Janreddy, D., Kuo, C.-W., Kuo, T.-S., Huang, H.-N., Yao, C.-F. (2014) Syntheses of indolo[1,2-a]quinazolinone derivatives via palladium catalyzed intramolecular C–H amidation. RSC Advances, 4(5), 2274–2283. https://doi.org/10.1039/c3ra44798g
35. Koubi, Y., Moukhliss, Y., Hajji, H., Abdessadak, O., Alaqarbeh, M., Aziz Ajana, M., Maghat, H., Lakhlifi, T., Bouachrine, M. (2024) Computational structure – biological activity and retrosynthesis investigations of 1,2,3-triazole-quinoline hybrid molecules as potential respiratory virus inhibitors. Chem. Heterocycl. Comp., 60, 491–504. https://doi.org/10.1007/s10593-024-03367-3
36. Li, Q.-Y., Cheng, S.-Y., Tang, H.-T., Pan, Y.-M. (2019) Synthesis of rutaecarpine alkaloids via electrochemical cross dehydrogenation coupling reaction. Green Chem., 21, 5517–5520. https://doi.org/10.1039/c9gc03028j
37. Liu, J.-Q., Dong, F., Zhang, W.-T., Wang, X.-S. (2017) An efficient synthesis of quinazoline or pyrrolo[1,2-a]quinazolin-5(1H)-one derivatives in ionic liquids catalyzed by iodine. Res. Chem. Intermed., 43(12), 6787–6801. https://doi.org/10.1007/s11164-017-3020-6
38. Liu, J.-Q., Zhang, W.-T., Wang, X.-S. (2018) The chemo-selective reaction of 2-amino-N′-arylbenzohydrazide and ketonic acid catalyzed by iodine for the synthesis of quinazoline derivatives. J. Heterocycl. Chem., 55(8), 1906–1916. https://doi.org/10.1002/jhet.3228
39. Liu, M., Shu, M., Yao, C., Yin, G., Wang, D., Huang, J. (2016) Synthesis of Pyrido-Fused Quinazolinone Derivatives via Copper-Catalyzed Domino Reaction. Org. Lett., 18(4), 824–827. https://doi.org/10.1021/acs.orglett.6b00113
40. Lu, J., Yu, L., Shi, J. (2013) Endogenous AMPKα2 Mediates the Inhibition of Biliary Fibroblasts Proliferation. Lett. Drug Des. Discov., 10, 522–528. https://doi.org/10.2174/1570180820666221031094240
41. Lu, L., Yang, K., Zhang, M.-M., Wang, X.-S. (2013) An efficient synthesis of pyrrolo[1,2-a]quinazoline derivatives in ionic liquid catalyzed by iodine. J. Heterocycl. Chem., 51(3), 841–845. https://doi.org/10.1002/jhet.1116
42. Ma, F., Du, H. (2017) Novel deoxyvasicinone derivatives as potent multitarget-directed ligands for the treatment of Alzheimer’s disease: Design, synthesis, and biological evaluation. Eur. J. Med. Chem., 140, 118–127. https://doi.org/10.1016/j.ejmech.2017.09.008
43. Mangla, V., Nepali, K., Singh, G., Singh, J., Guru, S., Gupta, M. K., Mahajan, P., Saxena, A. K., Lal Dhar, K. (2013) Strucure Activity Relationship of Arylidene Pyrrolo and Pyrido [2,1-b] Quinazolones as Cytotoxic Agents: Synthesis, SAR Studies, Biological Evaluation and Docking Studies. Med. Chem., 9(5), 642–650. https://doi.org/10.2174/1573406411309050003
44. Manzoor, S., Gabr, M. T., Rasool, B., Pal, K., Hoda, N. (2021) Dual targeting of acetylcholinesterase and tau aggregation: Design, synthesis and evaluation of multifunctional deoxyvasicinone analogues for Alzheimer’s disease. Bioorg. Chem., 116, 105354. https://doi.org/10.1016/j.bioorg.2021.105354
45. Mhaske, S. B., Argade, N. P. (2006) The chemistry of recently isolated naturally occurring quinazolinone alkaloids. Tetrahedron, 62(42), 9787–9826. doi:10.1016/j.tet.2006.07.098
46. Möhrle, H., Hemmerling, H.-J. (1978) Cyclodehydrierung von Anilinderivaten mit aromatischer Carbonsäureamid- oder Harnstoff-Funktion. Arch. Pharm., 311(7), 586–594. https://doi.org/10.1002/ardp.19783110705
47. Möhrle, H., Jeandrée, M. (1999) Chinazolinderivate durch cyclodehydrierung von N-(2-substituierten aryl)-piperidinen/quinazoline derivatives by cyclodehydrogenation of N-(2-substituted aryl)-piperidines. Z. fur Naturforsch. - B J. Chem. Sci., 54(12), 1577–1588. https://doi.org/10.1515/znb-1999-1217
48. Mondal, M. A., Mondal, S., Khan, A. A. (2020) A mechanistic insight into the acid catalyzed, one-pot synthesis of isoindole-fused quinazolin-4-ones. J. Chem. Sci., 132, 63. https://doi.org/10.1007/s12039-020-01768-3
49. Moored, J., Sutherlarnodg, E., Werbeyd, E., Kelly, W., Ermanod, S., Ebster, E. (1969) Reactions of Anthranilamide and o-Aminoacetophenone with Benzil and Benzoin. J. Org. Chem., 34(4), 887–892. https://doi.org/10.1021/jo01256a024
50. Moreira, N. M., dos Santos, J. R. N., Corrêa A. G. (2022) Greener synthesis of pyrroloquinazoline derivatives: Recent advances. Eur. J. Org. Chem., 2022, e202200369. https://doi.org/10.1002/ejoc.202200369
51. Naidu, S., Reddy, S. R. (2017) A green and recyclable Copper and ionic liquid catalytic system for the construction of poly-heterocyclic compounds via one-pot tandem coupling reaction. ChemistrySelect, 2(3), 1196–1201. https://doi.org/10.1002/slct.201601872
52. Nandy, P., Vishalakshi, M. T., Bhat, A. R. (2006) Synthesis and antitubercular activity of Mannich bases of 2-methyl-3H-quinazolin-4-ones. Indian J. Heterocycl. Chem., 15, 293–294.
53. Nazarenko, K. G., Shyrokaya, T. I., Tolmachev, A. A. (2003) Lactim ethers in the synthesis of 1,2-polymethylene-4-quinazolones. Synt. Commun., 33(2), 303–310. https://doi.org/10.1081/scc-120015716
54. Ostersehlt, B., Schlecker, R., Rendenbach, B., Von Philipsborn, G., Franke, A. (1993) Tetracyclic quinazoline derivatives, effective as antiarrythmic agents. U.S. Patent 5,214,047A.
55. Ozaki, K., Yamada, Y., Oine, T. (1983) Studies on 4(1H)-quinazolinones. III. Some derivatizations of 2-ethoxycarbonylalkyl-1-substituted-4(1H)-quinazolinones. Chem. Pharm. Bull., 31(7), 2234–2243. https://doi.org/10.1248/cpb.31.2234
56. Patil, N. T., Kavthe, R. D., Raut, V. S., Shinde, V. S., Sridhar, B. (2010) Gold- and Platinum-catalyzed formal Markownikoff’s double hydroamination of alkynes: A rapid access to tetrahydroquinazolinones and angularly-fused analogues thereof. J. Org. Chem., 75(4), 1277–1280. https://doi.org/10.1021/jo902293f
57. Patil, N. T., Lakshmi, P. G. V. V., Sridhar, B., Patra, S., Pal Bhadra, M., Patra, C. R. (2012) New linearly and angularly fused quinazolinones: Synthesis through Gold(I)-catalyzed cascade reactions and anticancer activities. Eur. J. Org. Chem., 2012(9), 1790–1799. https://doi.org/10.1002/ejoc.201101822
58. Potikha, L. M., Kovtunenko, V. A., Kisil, V. M. (2007) Condensed isoquinolines. 21. Condensation of o-bromomethylphenylacetonitrile with substituted anthranilic acids. Chem. Heterocycl. Compd., 43(4), 460–469. https://doi.org/10.1007/s10593-007-0066-1
59. Rasapalli, S., Sammeta, V. R., Murphy, Z. F., Golen, J. A., Agama, K., Pommier, Y., Savinov, S. N. (2021) Design and synthesis of C-aryl angular luotonins via a one-pot aza-Nazarov–Friedlander sequence and their Topo-I inhibition studies along with C-aryl vasicinones and luotonins. Bioorg. Med. Chem. Lett., 41, 127998. https://doi.org/10.1016/j.bmcl.2021.127998
60. Reddy, M. B., Prabhu, S., & Anandhan, R. (2023). Electrochemical reductive cascade cyclization of o-alkynylated derivatives for saturated amides/amines. Chem. Commun., 59(74), 11125-11128. https://doi.org/10.1039/D3CC03350C
61. Singh, P., Kaur, N., Banerjee, P. (2020) Regioselective Brønsted acid catalyzed annulation of cyclopropane aldehydes with N’-aryl anthranil hydrazides: Domino construction of tetrahydropyrrolo[1,2-a]quinazolin-5(1H)-ones. J. Org. Chem., 85, 3393−3406. https://doi.org/10.1021/acs.joc.9b03170
62. Stavytskyi, V., Antypenko, O., Nosulenko, I., Berest, G., Voskoboinik, O., Kovalenko, S. (2021) Substituted 3-R-2,8-Dioxo-7,8-dihydro-2H-pyrrolo[1,2-a][1,2,4] triazino[2,3-c]quinazoline-5a(6H)carboxylic Acids and their Salts – a Promising Class of Anti-inflammatory Agents. Antiinflamm. Antiallergy Agents Med. Chem., 20, 75–88. https://doi.org/10.2174/1871523019666200505073232
63. Sun, X., Hu, Y., Nie, S., Yan, Y., Zhang, X., Yan, M. (2013) Efficient construction of C=N double bonds via acceptorless dehydrogenative coupling. Adv. Synth. Catal., 355(11-12), 2179–2184. https://doi.org/10.1002/adsc.201300455
64. Sutherell, C. L., Tallant, C., Monteiro, O. P., Yapp, C., Fuchs, J. E., Fedorov, O., Siejka, P., Müller, S., Knapp, S., Brenton, J. D., Brennan, P. E., Ley, S. V. (2016) Identification and development of 2,3-dihydropyrrolo[1,2-a]quinazolin-5(1H)-one inhibitors targeting bromodomains within the switch/sucrose nonfermenting complex. J. Med. Chem., 59(10), 5095-5101. https://doi.org/10.1021/acs.jmedchem.5b01997
65. Sutherell, C., Ley, S. (2017) On the synthesis and reactivity of 2,3-dihydropyrrolo[1,2-a]quinazolin-5(1H)-ones. Synthesis, 49(01), 135–144. https://doi.org/10.1055/s-0035-1562792
66. Tang, C., Shao, J., Si, C., Yang, X., Hu, X., Li, P., Wang, X. (2024) Discovery of indole-3-acetic acid derivatives containing 1,3,4-thiadiazole thioether and amide moieties as novel antibacterial agents. Chem. Heterocycl. Comp., 60, 92–98. https://doi.org/10.1007/s10593-024-03298-z
67. Tian, K. M., Li, J. J., Xu, S. W. (2019) Rutaecarpine: A promising cardiovascular protective alkaloid from Evodia rutaecarpa (Wu Zhu Yu). Pharmacol. Res., 141, 541-550. doi: 10.1016/j.phrs.2018.12.019
68. Troschütz, R., Heinemann, O. (1995) On the Fluorescence Reaction of Parmaceutically Important o-Aminobenzamides and o-Aminobenzenesulfonamides with Phthalaldehyde and Analogues. Arch. Pharm., 328, 759–764. https://doi.org/10.1002/ardp.19953281106
69. Vangrevelinghe, E., Zimmermann, K., Schoepfer, J., Portmann, R., Fabbro, D., Furet, P. (2003) Discovery of a potent and selective protein kinase CK2 inhibitor by high-throughput docking. J. Med. Chem., 46, 2656-2662. https://doi.org/10.1021/jm030827e
70. Vaskevych, A., Dekhtyar, M., Vovk, M. (2024) Cyclizations of alkenyl(alkynyl)-functionalized quinazolinones and their heteroanalogues: A powerful strategy for the construction of polyheterocyclic structures. Chem. Rec., 24(2), e202300255. https://doi.org/10.1002/tcr.202300255
71. Vaskevych, A.I., Savinchuk, N.O., Vaskevych, R.I., Rusanov, E.B., Vovk, M.V. (2022). Chalcogenation/pyrrolo(pyrido)annulation of 2-(3-butenyl)quinazolin-4(3H)-ones by arylsulfenyl(selenyl) chlorides. Tetrahedron, 111(9), 132722. https://doi.org/10.1016/j.tet.2022.132722
72. Vaskevych, A.I., Savinchuk, N.O., Vaskevych, R.I., Rusanov, E.B., Grygorenko, O.O., Vovk, M.V. (2021). The PIFA-initiated oxidative cyclization of 2-(3-butenyl) quinazolin-4(3H)-ones – an efficient approach to 1-(hydroxymethyl)-2, 3-dihydropyrrolo [1,2-a] quinazolin-5 (1H)-ones. Beilst. J. Org. Chem., 17, 2787–2794. https://doi.org/10.3762/bjoc.17.189
73. Vaskevych, R. I., Vaskevych, A. I., Savinchuk, N. O., Stasevych, M. V., Shiskina S. V., Vovk M. V. (2024) Proton- and iodine-induced cyclization of 2-(pent-4-en-1-yl)quinazolin-4(3H)-ones: synthesis of pyrrolo[2,1-b]quinazolinone and pyrido[1,2-a]quinazolinone derivatives. Chem. Heterocycl. Comp., 60, 505–511. https://doi.org/10.1007/s10593-024-03368-2
74. Vaskevych, R.I., Savinchuk, N.O., Vaskevych, A.I., Rusanov, E.B., Bylina, V., Kyrylchuk, A.A., Vovk, M.V. (2023). Proton‐ and halogen‐induced cyclizations of 2‐(3‐butenyl)quinazolin‐4(3H)‐ones in the synthesis of pyrrolo[2,1‐b]‐ and pyrrolo[1,2‐а]quinazolinone derivatives. J. Heterocycl. Chem., 60(3), 431-448. https://doi.org/10.1002/jhet.4598
75. Vostrov, E.S., Gilev, D.V., Maslivets, A.N. (2004) Novel synthesis route for pyrrolo[1,2-a]quinazolines. Chem. Heterocycl. Compd., 40(4), 532–533. https://doi.org/10.1023/B:COHC.0000033556.58356.5c
76. Wang, M., Dou, G., Shi, D. (2010) Efficient and convenient synthesis of pyrrolo[1,2-a]quinazoline derivatives with the aid of Tin(II) chloride. J. Comb. Chem., 12(4), 582–586. https://doi.org/10.1021/cc100062e
77. Wang, Y.-Q., Huang, Z.-L., Chen, S.-B., Wang, C.-X., Shan, C., Yin, Q.-K., Huang, Z.-S. (2017) Design, Synthesis, and Evaluation of New Selective NM23-H2 Binders as c-MYC Transcription Inhibitors via Disruption of the NM23-H2/G-Quadruplex Interaction. J. Med. Chem., 60(16), 6924–6941. https://doi.org/10.1021/acs.jmedchem.7b00421
78. Wen, S., Du, Y., Liu,Y., Cui, X., Liu, Q., Zhou, H. (2022) Access to 2-arylquinazolin-4(3H)-ones through intramolecular oxidative C(sp3)–H/N‒H cross-coupling mediated by I2/DMSO. Eur. J. Org. Chem., e202101187. https://doi.org/10.1002/ejoc.202101187
79. Zadorozhny, A. V., Kovtunenko, V. A., Turov, A. V., Kucherenko, T. T. (2008) Condensed isoquinolines 32. Synthesis of 4H-thieno-[3′,2′:5,6]-and-[2′,3′:5,6]pyrimido-[1,2-b]isoquinolines and 6,12-dihydro-5H-isoquino-[2,3-a]quinazoline-5,12-dione derivatives. Chem. Heterocycl. Compd., 44(7), 845–851. https://doi.org/10.1007/s10593-008-0119-0
80. Zhang, W., Sun, J., Xu, F., Zhu, H., Yue, R., Zhang, Y., Niu, F. (2017) Reactions of 2-aminobenzohydrazide and 4-oxopimelic acid catalyzed by iodine in ionic liquids. Chin. J. Org. Chem., 37, 3191–3197. https://doi.org/10.6023/cjoc201706015
81. Zhang, W.-T., Qiang, W.-W., Yao, C.-S., Wang, X.-S. (2016) Iodine-catalyzed synthesis of fused tetracyclic pyridazino[6,1-b]pyrrolo[1,2-a]quinazolin-9(1H)-one derivatives via a tandem reaction. Tetrahedron, 72(17), 2178–2185. https://doi.org/10.1016/j.tet.2016.03.018
82. Zhao, H.-Y, Wang, H.-Y., Mao, S., Xin, M., Zhang, H., Zhang, S.-Q. (2017) Discovery of 2-(pyridin-2-yl)aniline as a directing group for the sp2 C–H bond amination mediated by cupric acetate. Org. Biomol. Chem., 15(31), 6622–6631. https://doi.org/10.1039/c7ob01353a
83. Zhao, R., Wen, S., Fu, H., Liu, M., Liu, Q., Zhou, H. (2022) Bis(2-methoxyethyl)ether promoted intramolecular acceptorless dehydrogenative coupling to construct structurally diverse quinazolinones by molecular oxygen. Green Chem., 24, 1644-1649. https://doi.org/10.1039/d1gc04581d
84. Zhao, X., Shi, D.-Q. (2011) An efficient synthesis of pyrrolo[1,2-a]quinazolin-5(1H)-one derivatives with the aid of low-valent titanium reagent. J. Heterocycl. Chem., 48(3), 634–638. https://doi.org/10.1002/jhet.637
85. Zhou, J.-X., Lu, L., Li, T.-J., Yao, C.-S., Wang, X.-S. (2014) A green synthesis of pyrrolo[1,2-a]quinazolin-5(1H)-one derivatives in ionic liquids catalyzed by iodine. J. Heterocycl. Chem., 51(5), 1472–1475. https://doi.org/10.1002/jhet.1768
86. Zicāne, D., Tetere, Z., Rāviņa, I., Turks, M. (2013) Synthesis of novel 4-aminotetrahydropyrrolo[1,2-a]quinazoline derivatives. Chem. Heterocycl. Compd., 49(2), 310–316. https://doi.org/10.1007/s10593-013-1248-7
87. Савінчук, Н., Васькевич, А., Салієва, Л., Сливка, Н., Вовк, М. (2023). Антиоксидантна дія 1-(арилсульфанілметил)˗2,3-дигідропіроло[1,2-а]хіназолін-5(1Н)-онів. Проблеми хімії та сталого розвитку, (2), 16–23. https://doi.org/10.32782/pcsd-2023-2-3
88. Савінчук, Н., Васькевич, А., Яковичук, Н., Грозав, А., Васькевич, А., Панчук, О., Салієва, Л., Сливка, Н., Вовк, М. (2022). Оцінка протимікробної дії халькогеновмісних піроло[1,2-а] хіназолін-5(1H)-онів. Проблеми хімії та сталого розвитку, (1), 54–63. https://doi.org/10.32782/pcsd-2022-1-8