Acta Scientific Medical Sciences (ASMS)(ISSN: 2582-0931)

Research Article Volume 4 Issue 9

Synthesis of Some Oxazine Compounds Derived from TDI and Schiff Bases

Ghufran T Sadeek, Mohammad S Al-Ajely* and Neam H Saleem

Chemistry Department, College of Education for Girls, College of Education for Pure Science, Mosul, Iraq

*Corresponding Author: Mohamed S AL-Ajely, Chemistry Department, College of Education for Girls, College of Education for Pure Science, Mosul, Iraq.

Received: August 05, 2020; Published: August 31, 2020

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Abstract

  It is known from ongoing research on heterocyclic compounds that these compounds are used as drug and drug carriers, According to FDI reports that these compounds forms 90% drug for cancer and 75% drugs for different diseases. It was also known from our studies on oxazine compounds that this type of heterocyclic compounds had versatile application in medicine. In this study, new 3,1-Benzoxazine compounds (S7-12) were prepared by cyclization reaction of some 2-(benzylidene-amino) benzoic acids (S1-6) with 2, 4- diisocyano1-methylbenzene (TDI) under reflex conditions in chloroform. The structure of the synthesized compounds were confirmed by IR, 1HNMR spectral studies.

Keywords: Oxazine Compounds; Insects; Fungi; 1HNMR

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References

  1. MKML Rai., et al. “Synthesis of new series of 5, 6-dihydro-4H-1, 2-oxazines via hetero Diels–Alder reaction and evaluation of antimicrobial activity”. European Journal of Medicinal Chemistry 44 (2009): 280-288.
  2. MJ Elarfi and HA Al-Difar. “Synthesis of some heterocyclic compounds derived from chalcones”. Scientific Review and Chemical Communications 2 (2012): 103-104.
  3. V Tiwari., et al. “Novel oxazine skeletons as potential antiplasmodial active ingredients: Synthesis, in vitro and in vivo biology of some oxazine entities produced via cyclization of novel chalcone intermediates”. Medicinal Chemistry 4 (2009): 4204-4206.
  4. BC Das., et al. “Design, synthesis and biological evaluation of 2H-benzo [b][1, 4] oxazine derivatives as hypoxia targeted compounds for cancer therapeutics”. Bioorganic and Medicinal Chemistry Letters15 (2009): 4204-4206.
  5. D Zhou., et al. “Studies toward the discovery of the next generation of antidepressants. Part 5: 3,4-Dihydro-2H-benzo[1,4] oxazine derivatives with dual 5-HT1A receptor and serotonin transporter affinity”. Bioorganic and Medicinal Chemistry Letters5 (2006): 1338-1341.
  6. S Wang., et al. “Novel hexacyclic camptothecin derivatives. Part 1: synthesis and cytotoxicity of camptothecin with A-ring fused 1,3-oxazine rin”. Bioorganic and Medicinal Chemistry Letters 14 (2008): 4095-4097.
  7. L Seal., et al. “An in vitro assessment of the antineoplastic potential of 2H-1, 3-Oxazine-2, 6 (3H)-dione (3-oxauracil) a novel pyrimidine”. Investigational New Drugs 4 (1997): 289-293.
  8. , et al. “Condensation products of aldehydes and ketones with o-aminobenzyl alcohol and o-hydroxybenzylamine”. Journal of the American Chemical Society 66 (1994): 1875.
  9. BP Mathew., et al. “An eco-friendly synthesis and antimicrobial activities of dihydro-2H-benzo- and naphtho-1,3-oxazine derivative”. European Medicinal Chemistry 45 (2010): 1502-1507.
  10. AK Verma., et al. “Silver-Catalyzed Domino Approach for the Synthesis of Benzoxazine/Oxazine-Fused Isoquinolines and Naphthyridines from o-Alkynyl Aldehydes”. Journal of Organic Chemistry 13 (2013): 6657-6669.
  11. SP Sakthinathan., et al. “Spectral correlations and antimicrobial activities of some (E)-N-Benzylidenepyridin-2-amines”. International LETTERS OF Chemistry, Physics and Astronomy 6 (2013): 77-90.
  12. MK Manjula., et al. “Synthesis of new series of 5,6-dihydro-4H-1,2-oxazines via hetero Diels–Alder reaction and evaluation of antimicrobial activity”. European Journal of Medicinal Chemistry 44 (2009): 280-288.
  13. X Wang., et al. “Influence of electronic effects from bridging groups on synthetic reaction and thermally activated polymerization of bisphenol‐based benzoxazines”. Journal of Polymer Science Part A: Polymer Chemistry 49 (2011): 1443-1452.
  14. Z Brunovska., et al. “1, 3, 5‐Triphenylhexahydro‐1, 3, 5‐triazine–active intermediate and precursor in the novel synthesis of benzoxazine monomers and oligomers”. Macromolecular Chemistry and Physics 200 (1999): 1745-1752.
  15. J Liu., et al. “Synthesis and surface properties of low surface free energy silane-functional polybenzoxazine films”. Langmuir 29 (2013): 411-416.
  16. WJ Burke., et al. “Condensation of Naphthols with Formaldehyde and Primary Amines”. Journal of the American Chemical Society 74 (1952): 3601-3605.
  17. WJ Burke., et al. “Bis-m-oxazines from Hydroquinon”. Journal of Organic Chemistry 26 (1961): 4403-4407.
  18. D Sicker and M Schulz. “Benzoxazinones in plants: occurrence, synthetic access, and biological activity”. Studies in Natural Products Chemistry 27 (2002): 185-232.
  19. P Zhang., et al. “Potent nonsteroidal progesterone receptor agonists: synthesis and SAR study of 6-aryl benzoxazines”. Bioorganic and Medicinal Chemistry Letters 12 (2002): 787-790.
  20. Hammet IP. Physical organic chemistry’Mc Graw-Hill Bokk Co. Ink. New York (1940).
  21. S Irani and F Nikpour. “An Efficient Approach for the synthesis of N-Phenyl carboxmaido-2-aryl-1,2-dihydro (4H)-3,1-benzoxazine-4-one”. Journal of the Iranian Chemical Society 4 (2010): 859-863.
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Citation

Citation: Mohamed S AL-Ajely., et al. “Synthesis of Some Oxazine Compounds Derived from TDI and Schiff Bases". Acta Scientific Medical Sciences 4.9 (2020): 120-128.




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