A Rapid Combinatorial Library Synthesis of Benzazolo[2,1-b]quinazolinones and Triazolo[2,1-b]quinazolinones

Document Type: Research Article

Authors

Faculty of Chemistry, Shahid Beheshti University, P.O. Box 19396-4716 Tehran, I.R. IRAN

Abstract

Benzazolo [2,1-b]quinazolinones and triazolo[2,1-b]quinazolinones were synthesized in high yields by the condensation reaction of an aldehyde and a cyclic  β-diketone with 2 - aminobenzimidazole, 2 - aminobenzothiazole or 1, 2, 4 - triazole derivatives in 1 - butyl - 3 -methylimidazolium bromide as an ionic liquid under classic heating conditions within 5-60 minutes. 

Keywords

Main Subjects


[1] Chai D., Fitch D. M., Propyl Hydroxylase Inhibitors. WO Patent 09039322 A1, March (2009).

[2] Kato F., Kimura H., Omatsu M., Yamamoto K., Miyamoto R., Preventive or Therapeutic Medicines for Diabetes Containing Fused-Heterocycle Compounds or Their Salts. WO Patent 02040485, May 23 ( 2002).

[3] McMaster B., Anti-Inflammatory Compositions and Methods of Use. WO Patent 03105857, December 24 ( 2003).

[4] Shigeta S., Mori S., Baba M., Hosoya M., Mochizuki N., Chiba T., De Clercq E., Inhibitory Effect of Pyridobenzoazoles on Orthomyxo- and Paramyxovirus Replication in Vitro, Antiviral Chem. Chemother., 3, p. 171 (1992).

[5] Nofal Z. M., Fahmy H. H., Mohamed, H. S., Synthesis, Antimicrobial and Molluscicidal Activities of New Benzimidazole Derivatives, Arch. Pharm. Res., 25, p. 28 (2002).

[6] Hafez A., Monem A. A., Benzimidazole Condensed Ring Systems: New Synthesis and Antineoplastic Activity of Substituted 3,4-dihydro- and 1,2,3,4-Tetrahydro-benzo[4,5]imidazo[1,2-a]pyrimidine Derivatives, Arch. Pharm. Res., 30, p. 678 (2007).

[7] Lunn W. H. W., Harper R. W., Stone R. L., Benzimidazo[2,1-b]quinazolin-12-ones. A New Class of Potent Immunosuppressive Compounds,    J. Med. Chem., 14, p. 1069 (1971).

[8] Alajarin R., Vaquero J. J., Alvarez-Builla J., Faude Casa-Juana M.,Sunkel C.,Priego J. G., Gomez-Sal P., Torres R., Imidazo[1,5-a]pyrimidine and Benzo[4,5]imidazo[1,2-a] pyrimidine Berivatives as Calcium Antagonists, Bioorg. Med. Chem., 2, p. 323 (1994).

[9] Ishida J., Wang H. K. Bastow K. F., Hu C. Q., Lee K. H., Antitumor Agents 201. Cytotoxicity of Harmine  and β-carboline Analogs, Bioorg. Med. Chem. Lett., 9, p. 3319 (1999).

[10]  Da Settimo A., Da Settimo F., Marini A. M., Primofiore G., Salerno S., Viola G., Dalla Via L., Magno S. M., Synthesis, DNA Binding and in Vitro Antiproliferative Activity of Purinoquinazoline, Pyridopyrimidopurine and Pyridopyrimidobenzimidazole Derivatives as Potential Antitumor Agents, Eur.J. Med. Chem., 33,  p. 685 (1998).

[11] Wu Y. C., Duh C. Y., Two New Natural Azafluorene Alkaloids and a Cytotoxic Aporphine Alkaloid from Polyalthialongifolia, J. Nat. Prod.,  53,p. 1327 (1990).

[12] He X. F., Wang X. N., Fan C. Q.,Gan L. S., Yin S.,Yue J. M., Chemical Constituents of Polyalthianemoralis, Helv. Chim. Acta., 90, p. 783(2007).

[13] Wendelin W., Gößnitzer E.,Abou El Ella D., Synthesis and Structure Elucidation of Pyrimidobenzimidazoles and Fused Derivatives II [1]. Dodecahydrobenzimidazo-[2,1-b]quinazolines and Decahydrobenzimidazo-[2,1-b] benzo [h] quinazolines[2], Monatsh. Chem., 131, p. 353 (2000).

[14] El Ella D. A., Gößnitzer E.,Wendelin W., Synthesis and Structural Elucidation of Pyrimido-[1,2-a] benzimidazoles and Fused Derivatives. I. Dihydropyrimido[1,2-a]benzimidazoles, J. Heterocyclic Chem., 33, p. 373 (1996).

[15] Lipson V. V., Desenko S. M.,  Ignatenko I. V.,  Shishkin O. V., Shishkina S. V., Synthesis and Chemical Transformations of Partially Hydrogenated [1,2,4]triazolo[5,1-b]quinazolines, Russ. Chem. Bull., 55, p. 345 (2006).

[16] Shikhaliev Kh. S., Kryl’skii D. V., Yu. Potapov A.,  Krysin M. Y., Synthesis of 8,8-R,R-8,9-dihydro[1,2,4]triazolo[1,5-a]quinazolin-6(7H )-ones, Russ. Chem. Bull., 54, p. 2903(2005).

[17] Shaabani A., Farhangi E., Rahmati A., Synthesis of Tetrahydrobenzimidazo[1,2-b]quinazolin-1(2H)-one and tetrahydro-1,2,4-triazolo[5,1-b]quinazolin-8(4H)-one Ring Systems under Solvent-free Conditions, Comb. Chem. High Throughput Screening, 9, p. 771 (2006).

[18] Lipson V. V.,   Desenko S. M., Borodina V. V., Shirobokova M. G.,Musatov V. I., Synthesis of Partially Hydrogenated 1,2,4-triazoloquinazolines by Condensation of 3,5-diamino-1,2,4-triazole with Rromatic Aldehydes and Dimedone, Russ. J. Org. Chem., 41, p. 114 (2005).

[19] Wasserscheid P., Welton T., “Ionic Liquids in Synthesis”, Wiley-VCH, (2003).

[20] Wasserscheid P., Keim W., Ionic liquids - New Solutions for Transition Metal Catalysis, Angew. Chem., Int. Ed., 39, p. 3773(2000).

[21] Cole A. C., Jensen J. L., Ntai I., Loan K., Tran K. L., Weaver T. K. J., Forbes D. C., Jr. DavisJ. H.,Novel Brønsted Acidic Ionic Liquids and Their use as Dual Solvent-catalysts, J. Am. Chem. Soc., 124, p. 5962 (2002).

[22] Welton T., Ionic liquids in catalysis, Cordin. Chem. Rev., 248, p. 2459 (2004).

[23] Jain N., Kumar A., Chauhan S., Chauhan S. M. S., Chemical and Biochemical Transformations in Ionic Liquids, Tetrahedron, 61, p. 1015(2005).

[24] Shaabani A., Rahmati A., Ionic Liquid Promoted Efficient Synthesis of 3,4-dihydropyrimidin-2-(1H)- ones, Catal. Lett., 100, p. 177 (2005).

[25] Shaabani A., Rahmati A., Naderi S., A Novel one-pot Three-component Reaction: Synthesis of Triheterocyclic 4H-pyrimido[2,1-b]benzazoles Ring Systems, Bioorg. Med. Chem. Lett., 15, p. 5553 (2005).

[26] Shaabani A., Soleimani E., Maleki A., Ionic Liquid Promoted One-pot Synthesis of 3-Aminoimidazo[1,2-a] pyridines, Tetrahedron Lett., 47, p. 3031 (2006).

[27] Shaabani A., Rezayan A. H., Rahmati A, Sharifi M., Ultrasound-Accelerated Synthesis of 1,4-dihydropyridines in an Ionic Liquid, Monatsh. Chem., 137,  p. 77 (2006).

[28] Chapman N. B., Gibson G. M., Mann F. G., Synthetic Antimalarials. Part XVI.                           4-Dialkylaminoalkylaminoquinazolines. Variation of Substituents in the 6- and 7-positions, J. Chem. Soc., p. 890 (1947).

[29] Liéby-Muller F., Simon C., Constantieux T., Rodriguez J., Current developments in Michael Addition-based Multicomponent Domino Reactions Involving 1,3-dicarbonyls and Derivatives, QSAR Comb. Sci., 25, p. 432 (2006).

[30] Simon C., Constantieux T., Rodriguez J., Utilisation of 1,3-dicarbonyl Derivatives in Multicomponent Reactions, Eur. J. Org. Chem., p. 4957 (2004).

[31] Shaabani A., Maleki A., Moghimi-Rad J., A Novel Isocyanide-based Three-component Reaction: Synthesis of Highly Substituted 1,6-dihydropyrazine-2,3-dicarbonitrile Derivatives, J. Org. Chem., 72, p. 6309 (2007).

[32] Shaabani A., Maleki A., Mofakham H., Moghimi-Rad J., A Novel One-pot Pseudo-five-component Synthesis of 4,5,6,7-tetrahydro-1H-1, 4-diazepine-5-carboxamide Derivatives, J. Org. Chem., 73, p. 3925 (2008).

[33] Shaabani A., Maleki A., Mofakham H., Khavasi H. R., Novel Isocyanide-based Three-component  Synthesis of 3,4-dihydroquinoxalin- 2-amine derivatives, J. Comb. Chem., 10, p. 323 (2008).

[34] Shaabani A., Maleki A., Mofakham H., Novel Multicomponent One-pot Synthesis of Tetrahydro-1H-1,5-benzodiazepine- 2-carboxamide Derivatives,      J. Comb. Chem., 10, p. 595 (2008).

[35] Shaabani A., Maleki A., Hajishaabanha F., MofakhamH.,Seyyedhamzeh M.,Mahyari M., Ng S. W., Novel Syntheses of Tetrahydrobenzodiazepines   and Dihydropyrazines via Isocyanide-based Multicomponent Reactions of Diamines, J. Comb. Chem., 12, p. 186 (2010).

[36] Shaabani A., Rezayan A. H., Sarvary A., Keshipour S., Ng S. W., A Novel One-pot Three-(in situ Five-) Component Condensation Reaction: An Unexpected Approach for the Synthesis of Tetrahydro-2,4-dioxo-1H-benzo[b][1,5] diazepine3-yl-2-methylpropanamide Derivatives, Org. Lett., 11, p. 3342 (2009).

[37] Shaabani A., Soleimani E., Rezayan A. H., Sarvary A., Khavasi H. R., Novel Isocyanide-based Four-Component Reaction: A Facile Synthesis of Fully Substituted 3,4-dihydrocoumarin Derivatives, Org. Lett., 10, p. 2581 (2008).

[38] Shaabani, A.; Mofakham, H.; Maleki, A.; Hajishaabanha, F., Novel Isocyanide-based One-pot Multicomponent Syntheses of Tetrahydrobenzo[ b] [1,4]oxazepine and Malonamide Derivatives, J. Comb. Chem., 12, p. 630 (2010).