American Journal of Materials Synthesis and Processing

Submit a Manuscript

Publishing with us to make your research visible to the widest possible audience.

Propose a Special Issue

Building a community of authors and readers to discuss the latest research and develop new ideas.

An Electron Bombardment Photodisintegration Spectrum Analysis of 3-Amino 6-methoxyl-2-MethylQuinazolin-4-(3H)-one Derivative

Background: The synthesis of new heterocyclic derivatives has attracted considerable attention. The explosive growth of heterocyclic chemistry is emphasized by the large number of research publications, monographs, and reviews. The heterocyclic organic compounds are extensively disseminated in natural and synthetic medicinal chemistry and are vital for human life. Looking at the previous studies on quinazolinones derivatives, only limited information is available on their mass spectral along with the preparation of novel quinazolin-4-(3H)-one derivatives. Objective: Aspiration of this investigation, was to synthesize a new 3-Amino-2-Methyl-6-methoxy-quinazolin-4-one was synthesized via the reaction between 2-Methyl-6-methoxy-benzo-1,3-oxazin-4-one and hydrazine hydrate and investigate their electron impact (EI) mass spectral disintegration. Method: The consolidation of 2-amino-methyl-5methoxybenzoate with acetic anhydride yielded the cyclic compound 2- methyl-4, 5-disubstituted-1, 3-benzo-oxazine-4-one which then produce a novel 2,3-disubstituted quinazolin-4 ones via the reaction with hydrazine hydrate. The compounds synthesized were enormously confirmed by means of Infrared, Nuclear Magnetic Resonance (1H and 13C), Gas Chromatography Mass Spectrophotometer and Elemental analysis. Discussion: The molecular ion of m/z 205 splints to give m/z 190 by loss of –NH group. The ion of m/z 190 was broken to give m/z 177 by losing CH group. This fragmented to m/z 162 by loss of –CH3 group and then m/z 136 by loss of CN group. The loss of O gave m/z 120 which fragment to give m/z 93 by loss of –HCN and finally gave m/z 65 by loss of CO group. Conclusion: The electron impact ionization mass spectra of compound 2 show a weak molecular ion peak and a base peak ofm/z 205 resulting from a break up fragmentation. Compound 2 give a characteristic fragmentation pattern. From the examination of the mass spectra of compound 2, it was found that the molecular ion had fragmented to the m/z 190. The final disintegration led to ion of m/z 93 and ion of mass m/z 65, respectively.

Mass Spectroscopy, Synthesis, Quinazoline-4-One, 2-Methyl 6-subtituted 1, 3-Benzo-Oxazine-4-One, 3-Amino-2-Methyl-6-methoxy-quinazolin-4-one, Nucleophile, Electron Impact Ionization Mass Spectra

APA Style

Osarumwense Peter Osarodion, Ayedun Hassan, Arigbede John. (2022). An Electron Bombardment Photodisintegration Spectrum Analysis of 3-Amino 6-methoxyl-2-MethylQuinazolin-4-(3H)-one Derivative. American Journal of Materials Synthesis and Processing, 7(1), 8-14. https://doi.org/10.11648/j.ajmsp.20220701.12

ACS Style

Osarumwense Peter Osarodion; Ayedun Hassan; Arigbede John. An Electron Bombardment Photodisintegration Spectrum Analysis of 3-Amino 6-methoxyl-2-MethylQuinazolin-4-(3H)-one Derivative. Am. J. Mater. Synth. Process. 2022, 7(1), 8-14. doi: 10.11648/j.ajmsp.20220701.12

AMA Style

Osarumwense Peter Osarodion, Ayedun Hassan, Arigbede John. An Electron Bombardment Photodisintegration Spectrum Analysis of 3-Amino 6-methoxyl-2-MethylQuinazolin-4-(3H)-one Derivative. Am J Mater Synth Process. 2022;7(1):8-14. doi: 10.11648/j.ajmsp.20220701.12

Copyright © 2022 Authors retain the copyright of this article.
This article is an open access article distributed under the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0/) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

1. Alagarsamy V., Pathak U. S., Sriram D., Pandeya S. N., Clercq E. De., Ind. J. Pharm. Sci., 62, 433—437 (2000).
2. Nigam R., Swarup S., Saxena V. K., Indian Drugs, 27, 238—243 (1990).
3. Koizomi M., Marakuni Y., Japan Kokai, 77, 51 (1917).
4. Hori M., Lemura R., Hara H., Ozaki A., Sukamoto T., Ohtaka H., Chem. Pharm. Bull., 38, 681—687 (1990).
5. Alagarsamy V., Raja Salomon V., Vanikavitha G., Paluchamy V., Ravichandran M., Arnald Sujin A., Thangathirupathy A., Amuthalakshmi S., Revathi R., Biol. Pharm. Bull., 25, 1432—1435 (2002).
6. Alagarsamy V., Muthukumar V., Pavalarani N., Vasanthanathan P., Revathi R., Biol. Pharm. Bull., 26, 557—559 (2003).
7. Alagarsamy V., Murugananthan G., Venkateshperumal R., Biol. Pharm. Bull., 26, 1711—1714 (2003).
8. Alagarsamy V., Rajesh R., Meena R., Vijaykumar S., Ramseshu K. V., Durai Anandakumar T., Biol. Pharm. Bull., 27, 652—656 (2004).
9. Zheng X, Li Z, Wang Y, Chen W, Huang Q, Liu C, Song G. Syntheses and insecticidal activities of novel 2,5-disubstituted 1,3,4-oxadiazoles. J Fluorine Chem. 2003; 123: 163-169. doi: 10.1016/S0022-1139(03)00168-4.
10. Chavan VP, Sonawane SA, Shingare MS, Karale BK. Synthesis, characterization, and biological activities of some 3,5,6-trichloropyridine derivatives. Chem Heterocyclic Compounds. 2006; 42: 625-630. doi: 10.1007/s10593-006-0137-8.
11. Hollaa BS, Gonsalves R, Shenoy S. Synthesis and antibacterial studies of a new series of 1,2-bis(1,3,4-oxadiazol-2-yl)ethanes and 1,2- bis(4-amino-1,2,4-triazol-3-yl)ethanes. Eur J Med Chem. 2000; 35: 267-271. doi: 10.1016/S0223-5234(00)00154-9.
12. Liu F, Luo X, Song B, Bhadury PS, Yang S, Jin L, Xue W, Hu D. Synthesis and antifungal activity of novel sulfoxide derivatives containing trimethoxyphenyl substituted 1,3,4-thiadiazole and 1,3,4-oxadiazole moiety. Bioorg Med Chem. 2008; 16: 3632-3640. doi: 10.1016/j.bmc.2008.02.006.
13. Narayana B, Raj KKV, Ashalatha BV, Kumari NS. Synthesis of some new 2-(6-methoxy-2-naphthyl)-5-aryl-1,3,4-oxadiazoles as possible non-steroidal anti-inflammatory and analgesic agents. Arch Pharm. 2005; 338: 373-377. doi: 10.1002/ardp.200500974.
14. Koksal M, Bilge SS, Bozkurt A, Sahin ZS, Isik S, Erol DD. Synthesis, characterization and anti-inflammatory activity of new 5-(3,4-dichlorophenyl)-2-(aroyl methyl)thio-1,3,4-oxadiaxoles. Arzneimittel-Forschung. 2008; 58: 510-514.
15. Zareef M, Iqbal R, Dominguez NG, Rodrigues J, Zaidi JH, Arfan M, Supuran CT. Synthesis and antimalarial activity of novel chiral and achiral benzenesulfonamides bearing 1,3,4- oxadiazole moieties. J Enz Inhib Med Chem. 2007; 22: 301-308. doi: 10.1080/14756360601114569.
16. Farghaly AR, El-Kashef H. Synthesis of some new azoles with antiviral potential1. Arkivoc. 2006; 11: 76-90. Synthesis and Antimicrobial Activity of 3-(1,3,4-Oxadiazol-2-yl)quinazolin-4(3H)-ones 191 Sci Pharm. 2010; 78: 171–193.
17. El-Essawy FA, Khattab AF, Abdel-Rahman AAH. Synthesis of 1,2,4-triazol-3-ylmethyl-, 1,3,4-oxa-, and -thiadiazol-2-ylmethyl-1H-[1,2,3]-triazolo[4,5-d]pyrimidinediones. Monatsh Chem. 2007; 138: 777-785. doi: 10.1007/s00706-007-0649-7.
18. Amr AEE, Mohamed SF, Abdel-Hafez NA, Abdalla MM. Antianexiety activity of pyridine derivatives synthesized from 2-chloro-6-hydrazino-isonicotinic acid hydrazide. Monatsh Chem. 2008; 139: 1491-1498. doi: 10.1007/s00706-008-0949-6.
19. Kumar A, D’Souza SS, Gaonkar SL, Rai KML, Salimath BP. Growth inhibition and induction of apoptosis in MCF-7 breast cancer cells by a new series of substituted-1,3,4-oxadiazole derivatives. Invest New Drugs. 2008; 26: 425-435. doi: 10.1007/s10637-008-9116-5.
20. Zareef M, Iqbal R, Al-Masoudi NA, Zaidi JH, Arfan M, Shahzad SA. Synthesis, anti–HIV, and antifungal activity of new benzensulfonamides bearing the 2,5-disubstituted1,3,4-oxadiazole moiety. Phosphorus Sulfur and Silicon. 2007; 182: 281-298. doi: 10.1080/10426500600919074.
21. Macaev F, Rusu G, Pogrebnoi S, Gudima A, Stingaci E, Vlad L, Shvets N, Kandemirli F, Dimogloa A, Reynolds R. Synthesis of novel 5-aryl-2-thio-1,3,4-oxadiazoles and the study of their structure-anti-mycobacterial activities. Bioorg Med Chem. 2005; 13: 4842-4850. doi: 10.1016/j.bmc.2005.05.011.
22. Zarghi A, Tabatabai SA, Faizi M, Ahadian A, Navabi P, Zanganeh V, Shafiee A. Synthesis and anticonvulsant activity of new 2-substituted-5-(2-benzyloxyphenyl)-1,3,4-oxadiazoles. Bioorg Med Chem Lett. 2005; 15: 1863-1865. doi: 10.1016/j.bmcl.2005.02.014.
23. Angelos SA, Meyers JA. The isolation and identification of precursors and reaction products in the clandestine manufacture of methaqualone and mecloqualone. J Forensic Sci. 1985; 30: 1022e1047.
24. Fukami H, Imajo S, Ito A, et al. Substituted 3- phenylsulfonylquinazoline-2,4-dione derivatives as novel nonpeptide inhibitors of human heart chymase. Drug Des Discov. 2000; 17: 69e84.
25. Ali SS, Sultan S. A mild and efficient synthesis of 2- substituted 2,3-dihydro-4(1H)-quinazolinones. Int J Res Pharm Biomed Sci. 2012; 3: 1511e1512.
26. Abdel-Jalil RJ, Voelter W, Saeed M. A novel method for the synthesis of 4(3H)-quinazolinones. Tetrahedron Lett. 2004; 45: 3475e3476.
27. Gupta S, Ajmera N. Solvent free synthesis of tetrazoles. Indian J Chem. 2009; 48: 853e863.
28. Kidwai M, Misra P. A convenient synthesis of tetrazoles. Synth Commun. 1999; 29: 3237e3243.
29. Hazarkhani H, Karimi B. A facile synthesis of new 3-(2- benzimidazoyl)-2-alkyl-4-(3H)-quinazolinones under microwave irradiation. Tetrahedron. 2003; 59: 4757e4764.
30. Salehi P, Debiri M, Zolfigol MA, Baghbanzadeh M. A new approach to the facile synthesis of mono- and disubstituted quinazolin-4(3H)-ones under solvent-free conditions. Tetrahedron Lett. 2005; 46: 7051e7058.
31. Priya MGR, Zulykama Y, Girija K, Murugesh S, Perumal PT. Synthesis of 4-(3H)-quinazolinones by microwave assisted tandem reaction and evaluation of their antibacterial and antifungal activities. Indian J Chem. 2011; 50B: 98e102.
32. Osarumwense Peter Osarodion, Edema Mary Orile, Usifoh Cyril Odianosen (2019). Electron Impact Ionization Mass Spectra of 3-Amino 5,6-dimethoxyl-2-methyl quinazolin-4-(3H)-one Derivative. American Journal of Materials Synthesis and Processing. Vol. 4, No. 2, 2019, pp. 62-67. doi: 10.11648/j.ajmsp.20190402.12.
33. Osarumwense Peter Osarodion, Omotade Treasure Ejodamen (2021). Electron Impact Ionization Mass Spectra of 3-Amino 6-Chloro-2-methyl Quinazolin-4-(3H)-one Derivatives. American Journal of Materials Synthesis and Processing 2021; 6 (1): 20-25. http://www.sciencepublishinggroup.com/j/ajmsp doi: 10.11648/j.ajmsp.20210601.13 ISSN: 2575-2154 (Print); ISSN: 2575-1530.