Abstract
A four-step synthetic route was developed for the synthesis of novel fused quinazolinones, quinazolino[3,4-a]quinazolinones, and isoinodolo[2,1-a]quinazolino[1,2-c]quinazolineones. Reaction of isatoic anhydride and different amines gave various 2-aminobenzamides. Then, reaction of 2-aminobenzamides with 2-nitrobenzaldehyde followed by the reduction of nitro group afforded 2-(2-aminophenyl)-3-aryl-2,3-dihydroquinazolin-4(1H)-one derivatives. Finally, reaction of the latter compounds with aromatic aldehydes or 2-formylbenzoic acid led to the formation of the corresponding products.
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Balaban AT, Oniciu DC, Katritzky AR (2004) Aromaticity as a cornerstone of heterocyclic chemistry. Chem Rev 104:2777–2812. doi:10.1021/cr0306790
Shafiee A (2015) Introduction for the special issue on bioactive heterocycles. Eur J Med Chem 97:334. doi:10.1016/j.ejmech.2015.03.043
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. doi:10.1016/j.ejmech.2014.10.084
Shiba SA, El-Khamry AA, Shaban ME, Atia KS (1997) Synthesis and antimicrobial activity of some bis-quinazoline derivatives. Pharmazie 52:189–194
Palaska E, Şahin G, Kelicen P, Durlu NT, Altinok G (2002) Synthesis and anti-inflammatory activity of 1-acylthiosemicarbazides, 1,3,4-oxadiazoles, 1,3,4-thiadiazoles and 1,2,4-triazole-3-thiones. Farmaco 57:101–107. doi:10.1016/S0014-827X(01)01176-4
Bartroli J, Turmo E, Algueró M, Boncompte E, Vericat ML, Conte L, Ramis J, Merlos M, García-Rafanell J, Forn J (1998) New azole antifungals. 3. Synthesis and antifungal activity of 3- substituted-\(4(3H)\)-quinazolinones. J Med Chem 41:1869–1882. doi:10.1021/jm9707277
Bhattacharjee AK, Hartell MG, Nichols DA, Hicks RP, Stanton B, van Hamont JE, Milhous WK (2004) Structure-activity relationship study of antimalarial indolo [2,1-b]quinazoline-6,12-diones (tryptanthrins). Three dimensional pharmacophore modeling and identification of new antimalarial candidates. Eur J Med Chem 39:59–67. doi:10.1016/j.ejmech.2003.10.004
Ma C, Li Y, Niu S, Zhang H, Liu X, Che Y (2011) \(N\)-Hydroxypyridones, phenylhydrazones, and a quinazolinone from isaria farinosa. J Nat Prod 74:32–37. doi:10.1021/np100568w
Stephen T, Stephen H (1956) 806. Syntheses in the quinazolone series. Part II. Synthesis of quino- and quinazo-quinazolones. J Chem Soc 4173–4177. doi:10.1039/JR9560004173
Butler K, Partridge MW, Waite JA (1960) 964. Cyclic amidines. Part XIV. Derivatives of \(7H\)-5,6a,12-triazabenz[\(a\)]anthracene. J Chem Soc 4970–4976. doi:10.1039/JR9600004970
Roy AD, Subramanian A, Roy R (2006) Auto-redox reaction: Tin(II) chloride-mediated one-step reductive cyclization leading to the synthesis of novel biheterocyclic 5,6-dihydro-quinazolino[4,3-\(b\)]quinazolin-8-ones with three-point diversity. J Org Chem 71:382–385. doi:10.1021/jo0518912
Hu Z, Li SD, Hong PZ (2010) Intramolecular cascade radical cyclizations promoted by samarium diiodide. Arkivoc (ix) 171–177. doi:10.3998/ark.5550190.0011.916
Bleda JA, Fresneda PM, Orenes R, Molina P (2009) Preparation of fused tetracyclic quinazolinones by combinations of aza-wittig methodologies and CuI-catalysed heteroarylation processes. Eur J Org Chem 2490–2504. doi:10.1002/ejoc.200900082
Venkateswarlu S, Satyanarayana M, Siddaiah V (2013) Facile one-pot synthesis of \(8H\)-quinazolino[4,3-\(b\)]quinazolin-8-ones. Synth Commun 43:85–92. doi:10.1080/00397911.2011.592258
Zeng F, Hn Alper (2010) One-step synthesis of quinazolino[3,2-\(a\)]quinazolinones via palladium-catalyzed domino addition/carboxamidation reactions. Org Lett 12:3642–3644. doi:10.1021/ol101428v
Alexandr FR, Berecibar A, Wrigglesworth R, Besson T (2003) Novel series of \(8H\)-quinazolino[4,3-\(b\)]quinazolin-8-ones via two Niementowski condensations. Tetrahedron 59:1413–1419. doi:10.1016/S0040-4020(03)00053-X
Kumar KS, Kumar PM, Kumar KA, Sreenivasulu M, Jafar AA, Rambabu Krishna GR, Reddy CM, Kapavarapu R, Shivakumar K, Priya KK, Parsa KL, Pal M (2011) A new three-component reaction: green synthesis of novel isoindolo[2,1-\(a\)]quinazoline derivatives as potent inhibitors of TNF-\(\alpha \). Chem Commun 47:5010–5012. doi:10.1039/C1CC10715A
Houlihan WJ, Lakes M (1970) Isoindoloquinazolines. US patent 3(509):147
Aeberli P, Houlihan WJ (1968) The reaction of some keto acids with anthranilic acid anthranilamides, orthanilamides, and salicylamide. J Org Chem 33:2402–2407. doi:10.1021/jo01270a051
Reddy GR, Reddy TR, Chary RG, Joseph SC, Mukherjee S, Pal M (2013) \(\beta \)-Cyclodextrin mediated MCR in water: synthesis of dihydroisoindolo[2,1-\(a\)]quinazoline-5,11-dione derivatives under microwave irradiation. Tetrahedron Lett 54:6744–6746. doi:10.1016/j.tetlet.2013.09.138
Sashidhara KV, Palnati GR, Dodda RP, Avula SR, Swami P (2013) Studies on novel synthetic methodologies, part XII: an efficient one-pot access to 6,6a-dihydroisoindolo[2,1-\(a\)]quinazoline-5,11-diones and 5-phenylisoindolo[2,1-\(a\)]quinazolin-11(6a\(H\))-ones. Synlett 24:105–113. doi:10.1055/s-0032-1317761
Saeedi M, Mahdavi M, Foroumadi A, Shafiee A (2013) Synthesis of novel fused 4,5-dihydro-1,2,3-triazolo[1,5-\(a\)][1,4] benzodiazepine derivatives via four-component Ugi-Smiles-type reaction. Tetrahedron 69:3506–3510. doi:10.1016/j.tet.2013.02.023
Mahdavi M, Asadi M, Saeedi M, Ebrahimi M, Rasouli MA, Ranjbar PR, Foroumadi A, Shafiee A (2012) One-pot, four-component synthesis of novel imidazo[2,1-\(b\)]thiazol-5-amine derivatives. Synthesis 44:3649–3654. doi:10.1055/s-0032-1317515
Esmaeili-Marandi F, Saeedi M, Mahdavi M, Yavari I, Foroumadi A, Shafiee A (2014) Potassium tert-butoxide promoted intramolecular amination of 1-aryl-2-(2-nitrobenzylidene)hydrazines: Efficient synthesis of 1-aryl-1\(H\)-indazoles. Synlett 25:2605–2608. doi:10.1055/s-0034-1379084
Mahdavi M, Asadi M, Saeedi M, Rezaei Z, Moghbel H, Foroumadi A, Shafiee A (2012) Synthesis of novel 1,4-benzodiazepine-3,5-dione derivatives: Reaction of 2-aminobenzamides under bargellini reaction conditions. Synlett 23:2521–2525. doi:10.1055/s-0032-1317297
Mahdavi M, Asadi M, Saeedi M, Tehrani MH, Mirfazli SS, Shafiee A, Foroumadi A (2013) Green synthesis of new boron-containing quinazolines: preparation of benzo[\(d\)][1,3,2]diazaborinin-4(1\(H\))-one derivatives. Synth Commun 43:2936–2942. doi:10.1080/00397911.2012.751612
Asadi M, Ebrahimi M, Mahdavi M, Saeedi M, Ranjbar PR, Yazdani F, Shafiee A, Foroumadi A (2013) Reaction of isatoic anhydride, amine, and \(N\), \(N\prime \)-dialkyl carbodiimides under solvent-free conditions: New and efficient synthesis of 3-alkyl-2-(alkylamino) quinazolin-4(3\(H\))-ones. Synth Commun 43:2385–2392. doi:10.1080/00397911.2012.714042
Shafii B, Saeedi M, Mahdavi M, Foroumadi A, Shafiee A (2014) Novel four-step synthesis of thioxo-quinazolino[3,4-\(a\)]quinazolinone derivatives. Synth Commun 44:215–221. doi:10.1080/00397911.2013.800211
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This research was supported by the grants from the research council of the Tehran University of Medical Sciences and Iran National Science Foundation (INSF).
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Mahdavi, M., Lotfi, V., Saeedi, M. et al. Synthesis of novel fused quinazolinone derivatives. Mol Divers 20, 677–685 (2016). https://doi.org/10.1007/s11030-016-9675-x
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DOI: https://doi.org/10.1007/s11030-016-9675-x