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
Volume 4, Issue 2, December 2019, Pages: 62-67
Received: Jun. 6, 2019;
Accepted: Jul. 8, 2019;
Published: Aug. 7, 2019
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Osarumwense Peter Osarodion, Department of Chemical Sciences, Ondo State University of Sciences and Technology, Okitipupa, Ondo State, Nigeria
Edema Mary Orile, Provost Office, College of Education, Warri, Delta State, Nigeria
UsifohCyril Odianosen, Faculty of Pharmaceutical Chemistry, University of Benin, Benin City, Nigeria
Background: The synthesis of novel 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 informationis available on their mass spectral along with the preparation of novel quinazolin-4-(3H)-one derivatives. Objective: Objective of this study, was to synthesize a novel 2-Methyl-6, 7-dimethoxy-quinazolin-4-one was synthesized via the reaction between 2-Methyl-6, 7-dimethoxy-benzo-1,3-oxazin-4-one andhydrazine hydrate and study their electron impact ( EI ) mass spectral fragmentation. Method: The condensation of 2-amino-methyl-4, 5-dimethoxybenzoate with acetic anhydride yielded the cyclic compound 2-methyl-4, 5-disubstituted-1, 3-benzo-oxazine-4-one which further produce a novel 2,3-disubstituted quinazolin-4 ones via the reaction with hydrazine hydrate. The compounds synthesized were unequivocally 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 235 fragment to give m/z 220 by loss of –NH group. The ion of m/z 220 was broken to give m/z 206 by losing CH2 group and fragment to m/z 177 by loss of HCO. 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 2show a weakmolecular ion peak and a base peak ofm/z 235resulting from a cleavage fragmentation. Compound 2 give a characteristic fragmentation pattern. From the study of the mass spectra of compound 2, it was found that the molecular ion had fragmented to the m/z 220. The final fragmentation led to ion of m/z 93 and ion of mass m/z 65, respectively.
Osarumwense Peter Osarodion,
Edema Mary Orile,
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.
Finar IL. (2007). Organic chemistry Volume 1, 6th Edition. P. 826.
Wikipedia, foundation. (2008).“Anti-inflammatory agents”. http://en.wikipedia.org/wiki/anti-inflammatory. Access 7, April, 2006.
Wikipedia. (2010). Quinazolinone encyclopedia. http://en.wikipedia.org/wiki/quinazoline. Access 27, April, 2006.
ShradhaSinha, Scrivastava, M. (1994). Cardiotonic, antihistamine, anti-fungal, antiviral, antimycobacteria and antimalarial activities of quinazolinone alkaloids. Prog. Drug Res. 43, 143.
Molina, P. Teraga, A. Gonzalez-Tejero, A. (2001). Anti-inflammatory Activity of some quinazolinone alkaloids.
Scrivatva, B. M.; Bhalla, V. K.; Shankar, T. N. (1993). Analgesic activity of some quinazolinone alkaloids. ArzneimForsch. 43, 596-600.
Hour MJ, Huang LJ, KuoSc, Xia Y, Bastow K, Nakanishi Y, Hamel E, Lee KH. (2000). 6-Alkylamino and 2, 3-dihydro-3-methoxy-2-phenyl-quinazolinone and related compounds: their synthesis, cytotoxicity and inhibition of tubulin polymerization. J. Med. Chem. 43, 4479-4487.
Hamel E, Lin CM, Ploueman J, Wang HK, Lee Kh, Paull KD. (1996). Antitumor Activities of 2, 3-dihydro-2(aryl)-4(1H)-quinazolinone derivatives. Interactions with tubulin. Biochem. Pharmacol. 51, 53-59.
Mayer, J. P.; Lewis, G. S. Curtis M. J.; Zhang. (1997). Antidiabetic activity of some quinazolinone alkaloids. J. Tetrahedron Lett. 389, 8445.
Jiang J. B. Hessan, D. P: Dusac; Dexter, D. L. Kag, G. J. Hamel, E. (1990). Anti-diabetic activity of some quinazolinone alkaloids. J. Med. Chem. 33, 1721.
A. Czarnik; Acc. Chem. Res, 1996, 29, 112.
A. Kozikowski; Comphrensive Heterocyclic Chemistry, Pergamon Press, 1984, 1,567.
Amar R. Desai and Kishor R. Desai, Niementowski reaction: microwave induced and conventional synthesis of quinazolinones and 3-methyl-1H-5-pyrazolones and their antimicrobial activity, ARKIVOC (xiii), 2005, 98-108.
Sachin S. Laddha, Satyendra p. Bhatnagar, A new therapeutic approach in Parkinson’s disease: some novel quinazoline derivatives as dual selective phosphodiesterase 1 inhibitors and anti-inflammatory agents. Bioorganic & Medicinal Chemistry Letters, 17, 2009, 6796–6802.
Abdel-Rahman AE, Bakhite EA, Al-Taifi EA. Synthesis and antimicrobial testing of some new Ssubstituted-thiopyridines, thienopyridines, pyridothienopyrimidines and pyridothienotriazines. Pharmazie 2003; 58: 372-377.
Chambhare, RV, Khadse BG, Bobde AS, Bahekar RH. Synthesis and preliminary evaluation of some N-[5- (2-furanyl)-2-methyl-4-oxo-4H-thieno[2,3-d]pyrimidin-3-yl]-carboxamide and 3-substituted-5- (2-furanyl)-2-methyl-3H-thieno[2,3-d]pyrimidin-4- ones as antimicrobial agents. Eur J Med Chem 2003; 38: 89-100.
Santagati NA, Caruso A, Cutuli VMC, Caccamo F. Synthesis and pharmacological evaluation of thieno[2,3-d]pyrimidin-2,4-dione and 5H-pyrimido [5,4-b]indol-2,4-dione derivatives. IlFarmaco 1995; 50: 689-695.