Abstract
Methyl α-[(4-oxoquinazolin-2-yl)thio]acetate (4) is one of the important heterocyclic compounds. It isused as a precursor to synthesis new derivatives of quinazolin-4-one moiety. The compound (4) was synthesized via a series of steps from anthranilic acid. The anthranilic acid was converted to its methyl ester (1) by esterification with methanol under acidic condition. The ester (1) was reacted with chloroacetyl chloride to produce methyl α-chloroacetamido benzoate (2). The chloro compound (2) was converted to the corresponding thiocyanato compound (3) by its reaction with ammonium thiocyanate. The thiocyanato compound (3) was cyclized to the target precursor (4) by boiling of compound (3) for 12 h. compound (4) was reacted with aromatic aldehydes under boiling condition to produce different hydrazones derivatives (5-12). The hydrazones compounds (5-12) were reacted with Chloroacetyl chloride to afforded the Azetedines compounds (13-20). The synthesized compounds were identified via the physical and spectral data.
Keywords
2-Mercapto quinazolin-4-one Methyl 2-chloroacetamido benzoate Methyl anthranilate Azetidene coumpounds Hydrazones derivatives Thiocyanato compound.
References
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Abstract
References
- Agarwal, K. C., Sharma, V., Shakya, N., & Gupta, S. (2009). Design and synthesis of novel substituted quinazoline derivatives as antileishmanial agents. Bioorganic & Medicinal Chemistry Letters, 19(18), 5474-5477.
- Al-Omary, F. A., Hassan, G. S., El-Messery, S. M., & El-Subbagh, H. I. (2012). Substituted thiazoles V. Synthesis and antitumor activity of novel thiazolo [2, 3-b] quinazoline and pyrido [4, 3-d] thiazolo [3, 2-a] pyrimidine analogues. European Journal of Medicinal Chemistry, 47, 65-72.
- Bhalla, M., Srivastava, V. K., Bhalla, T. N., & Shanker, K. (1993). Anti-inflammatory and analgesic activity of indolyl quinazolones and their congeners. Arzneimittel-forschung, 43(5), 595-600.
- Boyle, F. T., Matusiak, Z. S., Hughes, L. R., Slater, A. M., Stephens, T. C., Smith, M. N., ... & Jackman, A. L. (1993). Substituted-2-desamino-2-methyl-quinazolinones. A series of novel antitumour agents. In Chemistry and Biology of Pteridines and Folates (pp. 585-588). Springer.
- Crews, P., Rodriquez, J., Jaspars, M., & Crews, R. J. (1998). Organic structure analysis. Oxford University press.
- Decker, M., Kraus, B., & Heilmann, J. (2008). Design, synthesis and pharmacological evaluation of hybrid molecules out of quinazolinimines and lipoic acid lead to highly potent and selective butyrylcholinesterase inhibitors with antioxidant properties. Bioorganic & Medicinal chemistry, 16(8), 4252-4261.
- Anand, P. V., Kumar, K. S., Sivakumar, R., Solomon, W. S., & Jayaveera, K. N. (2009). Synthesis of quinazoline derivatives and their biological activities. Asian Journal of Chemistry, 21(9), 6656-6660.
- Vogels A.I.; (1994). Text book of practical organic chemistry (5th ed.). Longman Scientific & Technical.
- El-Badry, Y. A., Anter, N. M., & El-Hashash, M. A. (2014). Synthesis and behaviour of 2-(furan-2-yl) vinyl-4H-3, 1-benzoxazin-4-one towards nitrogen and carbon nucleophiles. Indian Journal of Chemistry, 53 ,1574-1583.
Details
| Primary Language | English |
|---|---|
| Subjects | Engineering |
| Journal Section | Articles |
| Authors | |
| Publication Date | December 31, 2021 |
| Published in Issue | Year 2021Volume: 16 |
