Silica Ammonium Acetate(SiO2-NH4OAc) Catalyzed Facial Synthesis of Dihydropyrazolo[4',3':5,6]Pyrano[2,3-d]Pyrimidine-5,7-Diones

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Silica ammonium acetate (SiO2-NH4OAc) was applied as an inexpensive, practical and heterogeneous catalyst for the preparation of new and known dihydropyrazolo[4',3':5,6]pyrano[2,3-d]pyrimidine-5,7-diones via one-pot four-component reaction of hydrazine hydrate, ethyl acetoacetate aldehydes and barbituric acid/dimethyl barbituric acid under solvent-free conditions. Silica supported ammonium acetate (SiO2-NH4OAc) was prepared according to easy procedure under ambient condition. After completion of the reaction, the catalyst was separated by filtration and reused. So, recycling system, simple work-up, using non-toxic materials, excellent yields and short reaction times makes our research green and convenient for preparation of these classes of organic compounds.

1. Biginelli, P. Synthesis of 3,4-dihydropyrimidin-2(1H)- ones. Gazz. Chim. Ital. 1983, 23, 360–413.

2. Hantzsh, A. Condensationsprodukte aus aldehydammoniak und ketonartigen verbindungen. Liebigs Ann. Chem. 1882, 1, 215–218.

3. Mannich, C.; Krosche W. Ueber ein Kondensationsprodukt aus Formaldehyd, Ammoniak und Antipyrin. Arch. Pharm. 1912, 250, 647–649.

4. Domling, A. Recent Developments in Isocyanide based multicomponent reactions in applied chemistry. Chem. Rev. 2006, 106, 17-89.

5. Anastas P.T.; Eqbali N. Green Chemistry: Principles and Practice. Chem. Soc. Rev. 2010, 39, 301–312.

6. Azzam, S.H.S.; Pasha, M.A. Simple and efficient protocol for the synthesis of novel dihydro-1H-pyrano[2,3-c]pyrazol-6-ones via a one-pot four-component reaction. Tetrahedron Lett. 2012, 53, 6834–6837.

7. Kamdar, N.R.; Haveliwala, D.D.; Mistry, P.T.; Patel, S.K. Design, synthesis and in vitro evaluation of antitubercular and antimicrobial activity of some novel pyranopyrimidines. Eur. J. Med. Chem. 2010, 45, 5056–5063.

8. McCoy, J.G.; Marugan, J.J.; Liu, K.; Zheng, W.; Southall, N.; Huang, W.; Heilig M.; Austin C.P. Selective Modulation of Gq/Gs pathways by Naphtho Pyrano Pyrimidines As Antagonists of the Neuropeptide S Receptor. ACS. Chem. Neur. 2010, 8, 559–574.

9. Prasad, Y.R.; Rao, A.L.; Prasoona L.; Murali K.; Kumar P.R. Synthesis and antidepressant activity of some 1,3,5-triphenyl-2-pyrazolines and 3-(2″-hydroxy naphthalen-1″-yl)-1,5-diphenyl-2-pyrazolines. Bioorg. Med. Chem. Letts. 2005, 15, 5030-5034.

10. Agarwal, A.; Ashutosh, R.; Goyal, N.; Chauhan, P.M.S.J. Dihydropyrido[2,3-d]pyrimidines as a new class of antileishmanial agents. Bioorg. Med. Chem. 2005, 13, 6678-6684.

11. Nadia M.R.; Nahed Y.K.; Fahmyb A.; El-Sayeda A.A.F. Facile synthesis of fused nitrogen containing heterocycles as anticancer agents. Der. Pharm. Chem. 2010, 2, 400-417.

12. Valderram, J.A.; Colonelli, P.; Vasquez, D.; Gonzalez, M.F.; Rodriguez, J.A.; Theoduloz, C. Studies on quinones. Part 44: Novel angucyclinone N-heterocyclic analogues endowed with antitumoral activity. Bioorg. Med. Chem. 2008, 16, 10172–10181.

13. Bagley, M.C.; Hughes D.D.; Lubinu M.C.; Merrit E.A.; Taylor P.H.; Tomkinson N.C.O. Microwave-assisted synthesis of pyrimidine libraries. QSAR & Comb. Sci. 2004, 23, 859-867.

14. Al-Kadasi, M.A.A.; Osman, H.A.; Nazeruddin, G.M. Silica Ammonium Acetate as an Efficient and Recyclable Heterogeneous Catalyst for Synthesis of 4H-pyran Derivatives under Ultrasound Irradiation at Ambient Conditions. Am. Chem. Sci. J. 2014, 4, 587-599.

15. Gupta R.; Gupta M.; Paul S.; Gupta R. Silica supported ammonium acetate: an efficient and recyclable heterogeneous catalyst for Knoevenagel condensation between adehydes or ketones and active methylene group in liquid phase. Bull. Kor. Chem. Soc. 2009, 30, 2419-2421.

16. Shaterian, H.R.; Rigi F. Starch sulfate as an efficient and biodegradable polymer catalyst for one-pot, four-component reaction of 2H-indazolo[2,1-b]phthalazine-triones. Starch 2011, 63, 340–346.

17. Shaterian, H.R.; Arman M.; Rigi F. Domino Knoevenagel condensation, Michael addition, and cyclization using ionic liquid, 2-hydroxyethylammonium formate, as a recoverable catalyst. J. Mol. Liq. 2011, 158, 145–150.

18. Shaterian, H.R.; Rigi, F. Acetalization of carbonyl compounds as pentaerythritol diacetals and diketals in the presence of cellulose sulfuric acid as an efficient, biodegradable and reusable catalyst. Chin. J. Chem. 2012, 30, 695-698.

19. Heravi, M.M.; Mousavizadeh, F.; Ghobadi, N.; Tajbakhsh, M. A green and convenient protocol for the synthesis of novel, pyrazolopyranopyrimidines via a one-pot, four-component reaction in water. Tetrahedron. Lett. 2014, 55, 1226-1228.

20. Li, X-T.; Zhao, A.D.; Moa L.P.; Zhang Z.H. Meglumine catalyzed expeditious four-component domino protocol for synthesis of pyrazolopyranopyrimidines in aqueous medium. RSC Adv. 2014, 4, 51580–51588.

21. Rigi, F.; Shaterian, H.R. Magnetic nanoparticle supported ionic liquid assisted green synthesis of pyrazolopyranopyrimidines and 1,6-diamino-2-oxo-1,2,3,4-tetrahydropyridine-3,5-dicarbonitriles. J. Chin. Chem. Soc. 2016, 63, 557-561.

22. Bakherada, M.; Doostia, R.; Mirzaeea, M.; Jadidib, K. Synthesis of pyrazolopyranopyrimidines catalyzed by caffeine supported on boehmite nanoparticles and their evaluation for anti-bacterial activities. Iran. J. Catal. 2017, 7, 27-35.

23. Sadjadi, S.; Heravi, M.M.; Daraie, M. Heteropolyacid supported on amine-functionalized halloysite nano clay as an efficient catalyst for the synthesis of pyrazolopyranopyrimidines via four-component domino reaction. Res. Chem. Intermed. 2017, 43, 2201-2214.

24. Nasresfahani, Z.; Kassaee, M.Z. Cu–Immobilized mesoporous silica nanoparticles [Cu2+@MSNs-(CO2−)2] as an efficient nanocatalyst for one-pot synthesis of pyrazolopyranopyrimidines in water. Chem. Select. 2017, 15, 9637 –9641.

Acta Chemica Iasi

The Journal of "Alexandru Ioan Cuza" University from Iasi

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