Efficient synthesis of a novel series of indeno fused pyrido[2,3-d]pyrimidines using β-cyclodextrin-propyl sulfonic acid as an eco-friendly catalyst

Prasanna Nithiya Sudhan1, Majid Ghashang2, Syed Sheik Mansoor1
1Research Department of Chemistry, Bioactive Organic Molecule Synthetic Unit, C. Abdul Hakeem College (Autonomous), Melvisharam 632 509, Tamil Nadu, India
2Department of Chemistry, Faculty of Sciences, Najafabad Branch, Islamic Azad University, Najafabad, Iran

Tài liệu tham khảo

Abdolmohammadi, 2012, Facile one-pot synthesis of pyrido[2,3-d]pyrimidine derivatives over ZrO2 nanoparticles catalyst, Chin Chem Lett, 23, 257, 10.1016/j.cclet.2012.01.001 Awoutters, 1986, Oral antiallergic activity in ascaris hypersensitive dogs: a study of known antihistamines and of the new compounds ramastine (R 57 959) and levocabastine (R 50 547), Drug Dev Res, 8, 95, 10.1002/ddr.430080112 Baharfar, 2011, A clean and efficient cyclocondensation to pyrido[2,3-d]pyrimidine derivatives in aqueous media, Chin Chem Lett, 22, 1183 Barvian, 2000, Pyrido[2,3-d]pyrimidin-7-one inhibitors of cyclin-dependent kinases, J Med Chem, 43, 4606, 10.1021/jm000271k Bennett, 1981, Antihypertensive activity of 6-arylpyrido[2,3-d]pyrimidin-7-amine derivatives, J Med Chem, 24, 382, 10.1021/jm00136a006 Broom, 1976, Pyrido[2,3-d]pyrimidines. IV. Synthetic studies leading to various oxopyrido[2,3-d]pyrimidines, J Org Chem, 41, 1095, 10.1021/jo00869a003 Degraw, 1974, Antimicrobial activity of 8-deazafolic acid, J Med Chem, 17, 470, 10.1021/jm00250a026 El-Gazzar, 2009, Synthesis of 4-substituted pyrido[2,3-d]pyrimidin-4(1H)-one as analgesic and anti-inflammatory agents, Bioorg Med Chem Lett, 19, 3392, 10.1016/j.bmcl.2009.05.044 Gangjee, 1996, 2,4-Diamino-5-deaza-6-substituted pyrido[2,3-d]pyrimidine antifolates as potent and selective non-classical inhibitors of dihydrofolate reductases, J Med Chem, 39, 1438, 10.1021/jm950786p Ghashang, 2013, Bull Korean Chem Soc, 34, 3289, 10.5012/bkcs.2013.34.11.3289 Ghashang, 2014, Pentafluorophenylammonium triflate (PFPAT) catalyzed facile construction of substituted chromeno[2,3-d]pyrimidinone derivatives and their antimicrobial activity, J Adv Res, 5, 209, 10.1016/j.jare.2013.03.003 Ghashang, 2014, Poly(4-vinylpyridinium)hydrogen sulfate: a novel and efficient catalyst for the synthesis of 13-aryl-indeno[1,2-b] naphtha[1,2-e] pyran-12(13H)-ones under solvent-free conditions, Chin J Catal, 35, 43, 10.1016/S1872-2067(12)60707-4 Ghashang, 2014, Thiourea dioxide: an efficient and reusable organocatalyst for the rapid one-pot synthesis of pyrano[4,3-b]pyran derivatives in water, Chin J Catal, 35, 127, 10.1016/S1872-2067(12)60727-X Gong, 2015, β-Cyclodextrin-butane sulfonic acid: an efficient and reusable catalyst for the multicomponent synthesis of 1-amidoalkyl-2-naphthols under solvent-free conditions, Green Chem, 17, 3141, 10.1039/C5GC00384A Gong, 2015, Efficient synthesis of 1,8-dioxo-octahydroxanthenes catalyzed by β-cyclodextrin grafted with butyl sulfonic acid in aqueous media, Chin J Catal, 36, 1249, 10.1016/S1872-2067(15)60888-9 Gong, 2015, β-Cyclodextrin-propyl sulfonic acid: a new and eco-friendly catalyst for one-pot multi-component synthesis of 3,4-dihydropyrimidones via Biginelli reaction, Tetrahedron, 71, 4830, 10.1016/j.tet.2015.05.028 Grivsky, 1980, Synthesis and antitumor activity of 2,4-diamino-6-(2,5-dimethoxybenzyl)-5-methylpyrido[2,3-d]pyrimidine, J Med Chem, 23, 327, 10.1021/jm00177a025 Harada, 1993, Synthesis of a tubular polymer from threaded cyclodextrins, Nature, 364, 516, 10.1038/364516a0 Harada, 2009, Cyclodextrin-based upramolecular polymers, Chem Soc Rev, 38, 875, 10.1039/b705458k Hasan, 1994, Reactions of 5-(p-anisyl)-2-methyl-7-(p-tolyl)-4H-pyrido[2,3-d][1,3]oxazin-4-one, Heterocycles, 38, 57, 10.3987/COM-91-5873 Hermecz, 1984, Nitrogen bridgehead compounds: new antiallergic 4H-pyrido[1,2-a]pyrimidin-4-ones, J Med Chem, 27, 1253, 10.1021/jm00376a003 Ibrahim, 2011, Design, synthesis and biological study of novel pyrido[2,3-d]pyrimidine as anti-proliferative CDK2 inhibitors, Eur J Med Chem, 46, 5825, 10.1016/j.ejmech.2011.09.041 Kiasat, 2012, Application of β-cyclodextrin-polyurethane as a stationary microvessel and solid–liquid phase-transfer catalyst: preparation of benzyl cyanides and azides in water, Catal Commun, 18, 102, 10.1016/j.catcom.2011.11.013 Kiasat, 2012, β-Cyclodextrin based polyurethane as eco-friendly polymeric phase transfer catalyst in nucleophilic substitution reactions of benzyl halides in water: an efficient route to synthesis of benzyl thiocyanates and acetates, Catal Sci Technol, 2, 1056, 10.1039/c2cy00375a Kiasat, 2014, β-Cyclodextrin–polyurethane polymer: a neutral and eco-friendly heterogeneous catalyst for the one-pot synthesis of 1,4-dihydropyridine and polyhydroquinoline derivatives via the Hantzsch reaction under solvent-free conditions, J Serb Chem Soc, 79, 401, 10.2298/JSC130112130K Kiyani, 2015, Solvent-free efficient one-pot synthesis of Biginelli and Hantzsch compounds catalyzed by potassium phthalimide as a green and reusable organocatalyst, Res Chem Intermediat, 41, 5177, 10.1007/s11164-014-1621-x Matsumoto, 1975, Pyrido[2,3-d]pyrimidine antibacterial agents. 3. 8-alkyl- and 8-vinyl-5,8-dihydro-5-oxo-2-(1-piperazinyl)pyrido[2,3-d]pyrimidine-6-carboxylic acids and their derivatives, J Med Chem, 18, 74, 10.1021/jm00235a017 Moreno, 2012, Sulfur and selenium derivatives of quinazoline and pyrido[2,3-d]pyrimidine: synthesis and study of their potential cytotoxic activity in vitro, Eur J Med Chem, 47, 283, 10.1016/j.ejmech.2011.10.056 Nemati, 2013, Nano-Fe3O4 encapsulated-silica particles bearing sulfonic acid groups as a magnetically separable catalyst for green and efficient synthesis of functionalized pyrimido[4,5-b]quinolines and indeno fused pyrido[2,3-d]pyrimidines in water, Chin Chem Lett, 24, 370, 10.1016/j.cclet.2013.02.018 Nia, 2013, A rapid one-pot synthesis of pyrido[2,3-d]pyrimidine derivatives using brønsted-acidic ionic liquid as catalyst, Acta Chim Slov, 60, 889 Pastor, 1994, Synthesis and structure of new pyrido[2,3-d]pyrimidine derivatives with calcium channel antagonist activity, Tetrahedron, 50, 8085, 10.1016/S0040-4020(01)85291-1 Quintela, 1997, Synthesis and antihistaminic activity of 2-guanadino-3-cyanopyridines and pyrido[2,3-d]-pyrimidines, Bioorg Med Chem, 5, 1543, 10.1016/S0968-0896(97)00108-9 Quiroga, 1998, Synthesis of 6-cyanopyrido[2,3-d]pyrimidinones in the reaction of 6-amino-4-pyrimidinones with arylidene derivatives of malonodinitrile, J Heterocycl Chem, 35, 1309, 10.1002/jhet.5570350612 Rad, 2015, Efficient one-pot synthesis of pyrido[2,3-d]pyrimidines catalysed by nanocrystalline MgO in water, Int Nano Lett, 5, 109, 10.1007/s40089-015-0145-8 Ran, 2015, β-Cyclodextrin-propyl sulfonic acid catalysed one-pot synthesis of 1,2,4,5-tetrasubstituted imidazoles as local anesthetic agents, Molecules, 20, 20286, 10.3390/molecules201119696 Sarmah, 2013, Efficient synthesis of dihydropyrido[4,3-d]pyrimidines by microwave-promoted three-component aza-Diels-Alder reaction, Tetrahedron Lett, 54, 267, 10.1016/j.tetlet.2012.11.018 Shaterian, 2014, One-pot, four-component synthesis of 2H-indazolo[2,1-b]phthalazine-triones catalyzed by cellulose-SO3H as a reusable heterogeneous and efficient catalyst, Res Chem Intermediat, 40, 1989, 10.1007/s11164-013-1096-1 Shirini, 2015, Facile synthesis of benzimidazole, benzoxazole, and benzothiazole derivatives catalyzed by sulfonated rice husk ash (RHA-SO3H) as an efficient solid acid catalyst, Res Chem Intermediat, 41, 5611, 10.1007/s11164-014-1685-7 Wang, 2004, KF-Alumina catalyzed one-pot synthesis of pyrido[2,3-d]pyrimidine derivatives, Synth Commun, 34, 4331, 10.1081/SCC-200039392 Wang, 2005, Three-component, one-pot synthesis of pyrido[2,3-d]pyrimidine derivatives catalyzed by KF-alumina, Synth Commun, 35, 1921, 10.1081/SCC-200064984 Youssif, 1999, A facile one-pot synthesis of pyrido[2,3-d]pyrimidines and pyrido[2,3-d:6,5-d′]dipyrimidines, J Chem Res (S), 1999, 112, 10.1039/a806513f Ziarani, 2014, One-pot synthesis of pyrido[2,3-d]pyrimidine derivatives using sulfonic acid functionalized SBA-15 and the study on their antimicrobial activities, J Saudi Chem Soc, 19, 676, 10.1016/j.jscs.2014.06.007