An Effective Method to Synthesize 2,3-Dihydroquinazolin-4(1H)- One Using Phosphate Fertilizers (MAP, DAP and TSP) as Green Heterogeneous Catalysts

Abstract

In this work, an efficient, easy, and green process has been developed for the synthesis of 2,3-dihydroquinazolin-4(1H)-one from a condensation reaction of anthranylamide with various aromatic aldehyde using of phosphate fertilizers, mono-ammonium phosphate (MAP), di-ammonium phosphate (DAP) and triple super phosphate (TSP) as heterogeneous catalysts. The reaction conditions were optimized taking into account of some parameters which control the reaction, namely the nature and the volume of the solvent and the mass of catalyst. The results show that the catalysts used herein are very interesting because they present a good catalytic activity and they are reusable for at least five cycles without any degradation of their activity.

Keywords

• Heterogeneous catalysis
• fertilizer phosphate
• MAP
• DAP

References

1. 1. Birch HL, Buckley GM, Davies N, Dyke HJ, Frost EJ, Gilbert PJ, et al. Novel 7-methoxy-6-oxazol-5-yl-2,3-dihydro-1H-quinazolin-4-ones as IMPDH inhibitors. Bioorg Med Chem Lett. 2005;15(23):5335-9.
2. 2. Cohen E, Klarberg B, Vaughan JR. QUINAZOLINONE SULFONAMIDES AS DIURETIC AGENTS. J Am Chem Soc. 1959;81(20):5508-9.
3. 3. Yadav MR, Shirude ST, Parmar A, Balaraman R, Giridhar R. Synthesis and anti-inflammatory activity of 2,3-diaryl-4(3H)-quinazolinones. ChemHeterocycl Compd. 2006; 42(8):1038-1045.
4. 4. Carlo M, Anna B, Isabella S, Maria S, Andrea R, Rosella F, et al. Synthesis and evaluation as NOP ligands of some spiro[piperidine-4,2’(1’H)-quinazolin]-4’(3’H)-ones 3 and spiro[piperidine-4,5’(6’H)-[1,2,4]triazolo[1,5-c]quinazolines]. Chem Pharm Bull (Tokyo). 2006;54(5):611-622.
5. 5. Bonola G, Da Re P, Magistretti MJ, Massarani E, Setnikar I. 1-Aminoacyl-2,3-dihydro-4(1H)-quinazolinone derivatives with choleretic and antifibrillatory activity. J Med Chem.1968;11(6):1136-9.
6. 6. Hess HJ, Cronin TH, Scriabine A. Antihypertensive 2-amino-4(3H)-quinazolinones. J Med Chem. 1968;11(1):130-6.
7. 7. Levin JI, Chan PS, Bailey T, Katocs AS, Venkatesan AM. The synthesis of 2,3-dihydro-4(1H)-quinazolinone angiotensin II receptor antagonists. Bioorg Med Chem Lett. 1994;4(9):1141-6.
8. 8. Okumura K, Oine T, Yamada Y, Hayashi G, Nakama M. 4-Oxo-1,2,3,4-tetrahydroquinazolines. I. Syntheses and pharmacological properties of 2-methyl-3-aryl-4-oxo-1,2,3,4-tetrahydroquinazolines and their 1-acyl derivatives. J Med Chem. 1968;11(2):348-52.

9. 9. Alagarsamy V, Solomon VR, Murugan M. Synthesis and pharmacological investigation of novel 4-benzyl-1-substituted-4H-[1,2,4]triazolo[4,3-a]quinazolin-5-ones as new class of H1-antihistaminic agents. Bioorg Med Chem. 2007;15(12):4009-15.
10. 10. Chinigo GM, Paige M, Grindrod S, Hamel E, Dakshanamurthy S, Chruszcz M, Minor W, Brown M. Asymmetric Synthesis of 2,3-Dihydro-2-arylquinazolin-4-ones: Methodology and Application to a Potent Fluorescent Tubulin Inhibitor with Anticancer Activity. J Med Chem. 2008;51(15):4620-31.
11. 11. White DC, Greenwood TD, Downey AL, Bloomquist JR, Wolfe JF. Synthesis and anticonvulsant evaluation of some new 2-substituted-3-arylpyrido[2,3-d]pyrimidinones. Bioorg Med Chem. 2004;12(21):5711-7.
12. 12. Sharma M, Chauhan K, Shivahare R, Vishwakarma P, Suthar MK, Sharma A, et al. Discovery of a New Class of Natural Product-Inspired Quinazolinone Hybrid as Potent Antileishmanial agents. J Med Chem. 2013;56(11):4374-92.
13. 13. Baghbanzadeh M, Salehi P, Dabiri M, Kozehgary G. Water-Accelerated Synthesis of Novel Bis-2,3-dihydroquinazolin-4(1 H )-one Derivatives. Synthesis. 2006;(2):344-8.
14. 14. Karimi-Jaberi Z, Arjmandi R. Acetic acid-promoted, efficient, one-pot synthesis of 2,3-dihydroquinazolin-4(1H)-ones. MonatshefteFürChem - Chem Mon. 2011;142(6):631-5.
15. 15. Niknam K, Mohammadizadeh MR, Mirzaee S. Silica-bonded S-sulfonic Acid as a Recyclable Catalyst for Synthesis of 2,3-Dihydroquinazolin-4(1H)-ones. Chin J Chem. 2011;29(7):1417-22.
16. 16. Yoo CL, Fettinger JC, Kurth MJ. Stannous Chloride in Alcohol: A One-Pot Conversion of 2-Nitro- N -arylbenzamides to 2,3-Dihydro-1 H -quinazoline-4-ones. J Org Chem. 2005;70(17):6941-3.
17. 17. Surpur MP, Singh PR, Patil SB, Samant SD. Expeditious One-Pot and Solvent-Free Synthesis of Dihydroquinazolin-4(1H)-ones in the Presence of Microwaves. Synth Commun. 2007;37(12):1965-70.
18. 18. Shaterian HR, Oveisi AR, Honarmand M. Synthesis of 2,3-Dihydroquinazoline-4(1 H )-ones. Synth Commun. 2010;40(8):1231-42.
19. 19. Kassaee MZ, Rostamizadeh S, Shadjou N, Motamedi E, Esmaeelzadeh M. An efficient one-pot solvent-free synthesis of 2,3-dihydroquinazoline-4(1H)-ones via Al/Al2O3 nanoparticles. J Heterocycl Chem. 2010;47(6):1421-4.
20. 20. Tarannum S, Ahmed N, Siddiqui ZN. LaCl3/nano-SiO2: A novel nanocatalyst for efficient synthesis of functionalized 2,3-dihydroquinazolinones. CatalCommun. 2015;66:60-6.
21. 21. Ghorbani-Choghamarani A, Azadi G. Synthesis, characterization, and application of Fe 3 O 4 -SA-PPCA as a novel nanomagnetic reusable catalyst for the efficient synthesis of 2,3-dihydroquinazolin-4(1H)-ones and polyhydroquinolines. RSC Adv. 2015;5(13):9752-8.
22. 22. Wu J, Du X, Ma J, Zhang Y, Shi Q, Luo L, Song B, Yang S, Hu D. Preparation of 2,3-dihydroquinazolin-4(1H)-one derivatives in aqueous media with β-cyclodextrin-SO3H as a recyclable catalyst. Green Chem. 2014;16(6):3210-3217.
23. 23. Abdollahi-Alibeik M, Shabani E. Nanocrystalline sulfated zirconia as an efficient solid acid catalyst for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones. J Iran Chem Soc. 2014;11(2):351-9.
24. 24. Yerram P, Chowrasia R, Seeka S, Tangenda SJ. Polyethylene glycol (PEG-400) as a medium for novel and efficient synthesis of 2-phenyl-2,3-dihydroquinazolin-4(1H)-one derivatives. Eur J Chem. 2013;4(4):462-6.
25. 25. Chen J, Su W, Wu H, Liu M, Jin C. Eco-friendly synthesis of 2,3-dihydroquinazolin-4(1H)-ones in ionic liquids or ionic liquid–water without additional catalyst. Green Chem. 2007;9(9):972.
26. 26. Bahammou I, Esaady A, Boukhris S, Ghailane R, Habbadi N, Hassikou A, et al. Direct use of mineral fertilizers MAP, DAP, and TSP as heterogeneous catalysts in organic reactions. Mediterr J Chem. 2016;5(6):615.
27. 27. Sibous S, Boukhris S, Ghailane R, Habbadi N, Hassikou A, Souizi A. easy synthesis of 3,4-dihydropyrimidin -2-(1h)-ones using phosphate fertilizers MAP, DAP and TSP as efficient catalysts. J Turk Chem. Soc Sect A Chem. 2017;4(2):477-488.
28. 28. Sibous S, Ghailane T, Houda S, Ghailane R, Boukhris S, Souizi A. Green and efficient method for the synthesis of 1,5-benzodiazipines using phosphate fertilizers as catalysts under free solvent. Mediterr J Chem. 2017;6(3):53.
29. 29. Wang M, Zhang TT, Song ZG. Eco-friendly synthesis of 2-substituted-2,3-dihydro-4(1H)-quinazolinones in water. Chin Chem Lett. 2011;22(4):427-30.
30. 30. Shaterian HR, Oveisi AR. PPA-SiO 2 as a Heterogeneous Catalyst for Efficient Synthesis of 2-Substituted-1,2,3,4-tetrahydro-4-quinazolinones under Solvent-free Conditions. Chin J Chem. 2009;27(12):2418-22.
31. 31. Benzekri Z, Serrar H, Boukhris S, Souizi A. FeCl3/Egg shell: An Effective Catalytic System for the Synthesis of 2,3-Dihydroquinazolin-4(1H)-ones at Room Temperature. J Turk Chem. Soc. Sect A Chem. 2017;4(3):775-786. 32. Chen J, Wu D, He F, Liu M, Wu H, Ding J, et al. Gallium(III) triflate-catalyzed one-pot selective synthesis of 2,3-dihydroquinazolin-4(1H)-ones and quinazolin-4(3H)-ones. Tetrahedron Lett. 2008;49(23):3814-8.
32. 33. Rostami A, Tavakoli A. Sulfamic acid as a reusable and green catalyst for efficient and simple synthesis of 2-substituted-2,3-dihydroquinazolin-4(1H)-ones in water or methanol. Chin Chem Lett. 2011;22(11):1317-20.
33. 34. Kancherla M, Badathala V. Aluminium exchanged Indian clay as an efficient reusable green catalyst for synthesis of 2, 3-dihydroquinazolin-4(1H)-one derivatives. J Porous Mater. 2017;24(5):1187-96.
34. 35. Vasudhevan S, Joel Karunakaran R. Synthesis, Characterisation of 2,3-Dihydroquinazolinone Derivatives and their Antimicrobial Studies. Int J ChemTech Res. 2013;5(6):2844-53.
35. 36. Shang Y-H, Fan L-Y, Li X-X, Liu M-X. Y(OTf)3-catalyzed heterocyclic formation via aerobic oxygenation: An approach to dihydroquinazolinones and quinazolinones. Chin Chem Lett. 2015;26(11):1355-8.
36. 37. Yassaghi G, Davoodnia A, Allameh S, Zare-Bidaki A, Tavakoli-Hoseini N. Preparation, Characterization and First Application of Aerosil Silica Supported Acidic Ionic Liquid as a Reusable Heterogeneous Catalyst for the Synthesis of 2,3-Dihydroquinazolin-4(1H)-ones. Bull Korean Chem Soc. 2012;33(8):2724-30.
37. 38. M W, J. J G, Z. G S, L W. Cerium(IV) ammonium nitrate catalyzed green synthesis of 2-substituted 2,3-dihydro- quinazolin-4(1H)-ones using a grinding technique. ChemHeterocycl Compd. 2011;47(7):851–855.
38. 39. Qiao RZ, Xu BL, Wang YH. A facile synthesis of 2-substituted-2,3-dihydro-4(1H)-quinazolinones in 2,2,2-trifluoroethanol. Chin Chem Lett. 2007;18(6):656-8.
39. 40. Karhale S, Survase D, Bhat R, Ubale P, Helavi V. A practical and green protocol for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones using oxalic acid as organocatalyst. Res ChemIntermed. 2017;43(7):3915-24.