Citation: Najmedin Azizi, Mahtab Edrisi. Practical approach to 2-thioxo-2, 3-dihydroquinazolin-4(1H)-one via dithiocarbamate-anthranilic acid reaction[J]. Chinese Chemical Letters, ;2017, 28(1): 109-112. doi: 10.1016/j.cclet.2016.06.012 shu

Practical approach to 2-thioxo-2, 3-dihydroquinazolin-4(1H)-one via dithiocarbamate-anthranilic acid reaction

Najmedin Azizi ^, ,
Mahtab Edrisi

Department of Green Chemistry, Chemistry & Chemical Engineering Research Center of Iran, P. O. Box 14335-186, Tehran, Iran

Corresponding author: Najmedin Azizi, azizi@ccerci.ac.ir
Received Date: 28 April 2016
Revised Date: 16 May 2016
Accepted Date: 26 May 2016
Available Online: 11 January 2016

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A practical and straightforward protocol has been developed for the preparation of 2-thioxo-2, 3-dihydroquinazolin-4(1H)-one derivatives from dithiocarbamate chemistry. The method involves the reaction of anthranilic acid derivatives (2-aminobenzoic acid, 2-aminobenzamide and isatoic anhydride) with various dithiocarbamate derivatives using ethanol as solvent. The main advantages of this protocol include practical simplicity, good to high yields, and ease of product isolation, purification and cheapness of the solvent.
- Dithiocarbamate,
- Anthranilic acid,
- 2-Thioxo-2, 3-dihydroquinazolin-4(1H)-one,
- 2-Aminobenzoic acid,
- 2-Aminobenzamide,
- Isatoic anhydride
1. [1]
  Ismail M.A.H., Barker S., El Ella D.A.A.. Design and synthesis of new tetrazolyl-and carboxy-biphenylylmethyl-quinazolin-4-one derivatives as angiotensin Ⅱ AT1 receptor antagonists[J]. J. Med. Chem., 2006,49:1526-1535. doi: 10.1021/jm050232e
2. [2]
  Mhaske S.B., Argade N.P.. The chemistry of recently isolated naturally occurring quinazolinone alkaloids[J]. Tetrahedron, 2006,62:9787-9826. doi: 10.1016/j.tet.2006.07.098
3. [3]
  Koepfli J.B., Brockman J.A., Moffat J.. The structure of febrifugine and isofebrifugine[J]. J. Am. Chem. Soc., 1950,723323.
4. [4]
  Choo H.Y.P., Kim M., Lee S.K., Kim S.W., Chung I.K.. Solid-phase combinatorial synthesis and cytotoxicity of 3-aryl-2, 4-quinazolindiones[J]. Bioorg. Med. Chem., 2002,10:517-523. doi: 10.1016/S0968-0896(01)00299-1
5. [5]
  Panchompoo J., Aldous L., Kabeshov M.. A green approach to Fenton chemistry:mono-hydroxylation of salicylic acid in aqueous medium by the electrogeneration of Fenton's reagent[J]. New J. Chem., 2012,36:1265-1272. doi: 10.1039/c2nj21007j
6. [6]
  He L., Li H., Chen J., Wu X.F.. Recent advances in 4(3H)-quinazolinone syntheses[J]. RSC Adv., 2014,4:12065-12079. doi: 10.1039/c4ra00351a
7. [7]
  Li W.Y., Zong Y.X., Wang J.K., Niu Y.Y.. Sulfonated poly (4-vinylpyridine) heteropolyacid salts:a reusable green solid catalyst for Mannich reaction[J]. Chin. Chem. Lett., 2014,25:575-578. doi: 10.1016/j.cclet.2013.11.022
8. [8]
  Alexandre F.R., Berecibar A., Besson T.. Microwave-assisted Niementowski reaction. Back to the roots[J]. Tetrahedron Lett, 2002,43:3911-3913. doi: 10.1016/S0040-4039(02)00619-6
9. [9]
  Oschatz S., Brunzel T., Wu X.F., Langer P.. Catalyst-free synthesis of 2-aryl-1, 2-dihydro-quinazolin-4(1H)-thiones from 2-aminobenzothio-amides and aldehydes in water[J]. Org. Biomol. Chem., 2015,13:1150-1158. doi: 10.1039/C4OB02207F
10. [10]
  Chen J., Natte K., Neumann H., Wu X.F.. A convenient palladium-catalyzed carbonylative synthesis of quinazolines from 2-aminobenzylamine and aryl bromides[J]. RSC Adv., 2014,4:56502-56505. doi: 10.1039/C4RA11303A
11. [11]
  He L., Sharif M., Neumann H., Beller M., Wu X.F.. A convenient palladiumcatalyzed carbonylative synthesis of 4(3H)-quinazolinones from 2-bromoformanilides and organo nitros with Mo (CO)₆ as a multiple promoter[J]. Green Chem., 2014,16:3763-3767. doi: 10.1039/C4GC00801D
12. [12]
  Zhang Z., Wang M., Zhang C.. The cascade synthesis of quinazolinones and quinazolines using an α-MnO₂ catalyst and tert-butyl hydroperoxide (TBHP) as an oxidant[J]. Chem. Commun., 2015,51:9205-9207. doi: 10.1039/C5CC02785C
13. [13]
  Kumar D., Jadhavar P.S., Nautiyal M.. Convenient synthesis of 2, 3-disubstituted quinazolin-4(3H)-ones and 2-styryl-3-substituted quinazolin-4(3H)-ones:applications towards the synthesis of drugs[J]. RSC Adv., 2015,5:30819-30825. doi: 10.1039/C5RA03888J
14. [14]
  Tanwar B., Purohit P., Raju B.N.. An "all-water" strategy for regiocontrolled synthesis of 2-aryl quinoxalines[J]. RSC Adv., 2015,5:11873-11883. doi: 10.1039/C4RA16568C
15. [15]
  Rahman M., Ling I., Abdullah N., Hashim R., Hajra A.. Organocatalysis by p-sulfonic acid calix[J]. RSC Adv., 2015,5:7755-7760. doi: 10.1039/C4RA16374E
16. [16]
  Wang X.S., Yang K., Zhou J., Tu S.J.. Facile method for the combinatorial synthesis of 2, 2-disubstituted quinazolin-4(1H)-one derivatives catalyzed byiodine in ionic liquids[J]. J. Comb. Chem., 2010,12:417-421. doi: 10.1021/cc900174p
17. [17]
  Shang Y.H., Fan L.Y., Li X.X., Liu M.X.. Y (OTf)₃-catalyzed heterocyclic formation via aerobic oxygenation:an approach to dihydro quinazolinones and quinazolinones[J]. Chin. Chem. Lett., 2015,26:1355-1358. doi: 10.1016/j.cclet.2015.07.026
18. [18]
  Alagarsamy V., Solomon V.R., Murugan M.. Synthesis and pharmacological investigation of novel 4-benzyl-1-substituted-4H-[J]. Bioorg.Med.Chem., 2007,15:4009-4015. doi: 10.1016/j.bmc.2007.04.001
19. [19]
  Gomathi G., Dar S.H., Thirumaran S., Ciattini S., Selvanayagam S.. Bis (N-benzyl-N-furfuryldithiocarbamato-S, S0) mercury (Ⅱ) as a precursor for the preparation of mercury sulfide nanoparticles[J]. Compt. R. Chim., 2015,18:499-510. doi: 10.1016/j.crci.2014.10.003
20. [20]
  Bahekar S.P., Dahake N.D., Sarode P.B., Chandak H.S.. Efficient access to 2, 3-dihydroquinazolin-4(1H)-ones by environmentally benign l-proline nitrate as recyclable catalyst[J]. Synlett, 2015:2575-2577.
21. [21]
  Devi N.S., Singh S.J., Singh O.M.. An efficient one-pot multicomponent synthesis of 2, 3-dihydro-3-alkyl/aryl-2-thioxoquinazolin-4(1H)-ones under solvent-free conditions[J]. Synlett, 2012:2111-2125.
22. [22]
  Azizi N., Saidi M.R.. Chemoselective and convenient preparation of 1, 1-diacetates from aldehydes, mediated by solid lithium perchlorate under solvent-free conditions[J]. J. Mole. Catal. A:Chem., 2005,238:138-141. doi: 10.1016/j.molcata.2005.05.022
23. [23]
  Mahmoud M.R., Abou W.S.I., Elmagd -, Abdelwahab S.S., Soliman E.S.A.. Spectral characterization of novel 3-phenyl-2-substituted quinazoline and fused quinazoline derivatives[J]. Syn. Commun., 2013,43:1484-1490. doi: 10.1080/00397911.2011.642924
24. [24]
  Ghiviriga I., El-Dien B., El-Gendy M., Steel P.J., Katritzky A.R.. Tautomerism of guanidines studied by 15N NMR:2-hydrazono-3-phenylquinazolin-4(3H)-ones and related compounds[J]. Org. Biomol. Chem., 2009,7:4110-4119. doi: 10.1039/b907577a
25. [25]
  Rao A.V.D., Vykunteswararao B.P., Bhaskarkumar T.. Sulfonic acid functionalized Wang resin (Wang-OSO₃H) as polymeric acidic catalyst for the eco-friendly synthesis of 2, 3-dihydroquinazolin-4(1H)-ones[J]. Tetrahedron Lett., 2015,56:4714-4717. doi: 10.1016/j.tetlet.2015.06.004
26. [26]
  El-Sharief1 A.M.Sh., Ammar Y.A., Mohamed Y.A., El-Gaby M.S.A.. A comparative study of the behavior of cyanothioformamide and oxazolidine (thiones or iminothiones) towards some binucleophiles[J]. Heteroat. Chem., 2002,13:291-298. doi: 10.1002/(ISSN)1098-1071
27. [27]
  Pawlewski Br.. Ueber die Synthesen der Ketochinazolinderivate[J]. Chem. Ber., 1906,39:1732-1736. doi: 10.1002/(ISSN)1099-0682
28. [28]
  Raghavendra G.M., Pavan Kumar C.S., Suresha G.P., Rangappa K.S., Mantelingu K.. T³P catalyzed one pot three-component synthesis of 2, 3-disubstituted 3H-quinazolin-4-ones[J]. Chin. Chem. Lett., 2015,26:963-968. doi: 10.1016/j.cclet.2015.03.037
29. [29]
  Azizi N., Saidi M.R.. Lithium perchlorate diethyl ether solution:a highly efficient media for the abramov reaction[J]. Phosphorus Sulfur Silicon Relat Elem., 2003,178:1255-1259. doi: 10.1080/10426500307904
30. [30]
  Mehta V.N., Kailasa S.K.. Malonamide dithiocarbamate functionalized gold nanoparticles for colorimetric sensing of Cu²⁺ and Hg²⁺ ions[J]. RSC Adv., 2015,5:4245-4255. doi: 10.1039/C4RA11640B
31. [31]
  Azizi N., Ebrahimi F., Akbari E., Aryanasab F., Saidi M.R.. Waste-free and environment-friendly uncatalyzed synthesis of dithiocarbamates under solvent-free conditions[J]. Synlett, 2007:2797-2800.
32. [32]
  Chaturvedi D., Ray S.. An efficient, one-pot, synthesis of dithiocarbamates from the corresponding alcohols using Mitsunobu's reagent[J]. Tetrahedron Lett., 2006,47:1307-1309. doi: 10.1016/j.tetlet.2005.12.079
33. [33]
  Azizi N., Mirmashhori B., Saidi M.R.. Lithium perchlorate promoted highly regioselective ring opening of epoxides under solvent-free conditions[J]. Catal. Commun., 2007,8:2198-2203. doi: 10.1016/j.catcom.2007.04.032
34. [34]
  Chaturvedi D., Mishra N., Mishra V.. An efficient, one-pot synthesis of S-alkyl thiocarbamates from the corresponding thiols using the Mitsunobu reagent[J]. Synthesis, 2008:355-357.
35. [35]
  Azizi N., Batebi E.. Highly efficient deep eutectic solvent catalyzed ring opening of epoxides[J]. Catal. Sci. Technol., 2012,2:2445-2448. doi: 10.1039/c2cy20456h
36. [36]
  Azizi N., Gholibeglo E.. A highly efficient synthesis of dithiocarbamates in green reaction media[J]. RSC Adv., 2012,2:7413-7416. doi: 10.1039/c2ra20615c
37. [37]
  Chan C.H., Shish F.J., Liu K.C., Chern J.W.. A facile preparation of 3-substituted 2-thioxo-tetrahydoquinazolin-4-ones by the reaction of anthranilamide with isothiocynates[J]. Heterocycles, 1987,26:3193-3196. doi: 10.3987/R-1987-12-3193
38. [38]
  Alagarsamy V., Parthiban P.. Design and synthesis of novel 3-(phenyl)-2-(3-substituted propylthio) quinazolin-4-(3H)-ones as a new class of H1-antihistaminic agents[J]. J. Heterocyclic Chem., 2014,51:1615-1620. doi: 10.1002/jhet.v51.6
39. [39]
  Wang M.M., Dou G.L., Shi D.Q.. One-pot synthesis of 2, 3-dihydro-2-thioxoquinazolin-4(1H)-ones from nitro-compounds with the aid of tin (Ⅱ) chloride[J]. J. Heterocyclic Chem., 2010,47:939-943. doi: 10.1002/jhet.392
40. [40]
  Liu W., Zhang Q., Gong F., Cao Z., Huo Y.. A convenient and efficient synthesis of 2-thioxoquinazolinone derivatives via microwave irradiation[J]. J. Heterocyclic Chem., 2015,52:317-321. doi: 10.1002/jhet.v52.2
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