Molbank 2005, M448

http://www.mdpi.net/molbank/

 

Synthesis of 4H-3,1-benzoxazin-4-one 2-phenyl Using Cyanuric Chloride as a Cyclization Agent

 

Sohrab Abdollahi* and Mehdi Shariat

 

Department of Chemistry

Payamnoor University of  Golpayegan,

Golpayegan Iran

e-mail: [email protected]

 

Received: 15 July 2005 / Accepted: 24 October 2004 / Published: 12 December 2005

 

Keywords:

 

      

 

The preparation of different derivatives of benzoxazinone can be considered important because they have different kinds of pharmaceutical, agricultural and industrial applications [1-4]. The synthesis of benzoxazinone derivative, 4H-3,1-benzoxazin-4-one 2-(N-phthaloylmethyl), was reported previously by our team [5]. In this paper we have used the same method to synthesize 4H-3,1-benzoxazin-4-one 2-phenyl 5. This synthesis occurs in two steps: In the first step, anthranilic acid 1 (4.11g) in 40 ml chloroform was mixed with 4.15 ml anhydrous triethylamine and 3.48 ml benzoyl chloride 2 in 10 ml chloroform. In the second step, the resulting benzamid 3 (2.41 g) mixed with 100 ml anhydrous toluene, 1.52 ml triethylamine and 1.84 g cyanuric chloride 4 is refluxed for one week. After purification, drying with magnesium sulfate, the resulting benzoxazinone 5 as a final product is recrystallized in 30% ether-chloroform solution. Yield 67.8 % (63% overall)

 

For the compound 3:

 

1H-NMR (CDCl3): ¦Ä= 7.10-9.13 (m, 9H, Ar-H; NH); 12.1-12.3 (broad singlet,-COOH).

 

IR (KBr, cm-1): 2460 ¨C 3115; 1680; 1639.

 

For the product 5 

 

Melting point: 122-124ºC (lit. 123-125) [6].

 

1H-NMR (CDCl3): ¦Ä= 7.25-8.73 (m, 9H, Ar-H).

 

IR (KBr, cm-1): 1760; 1608.

 

Elemental Analysis: Calculated for C14H9NO2 (223.23): C, 75.33%; H, 4.06%; N, 6.27%; O, 14.33.  Found: C, 75.01%; H, 4.26%; N, 6.3%; O, 14.43%.

 

Acknowledgement

The authors are grateful for the support and financial help that were received by the University of Payamnoor.

 

References

1. Bulluci, C.; Gualtieri, F.;  Chiarini, A.  Eur. J. Med. Chem. 1987, 22, 473.

2. Wiker,  P.;  Wilson, A.  J. Am. Chem. Soc. 1955, 77, 5598.

3. Bouillant, M. L.; Farre-Bonvin, J.; Ricci, P. Tetrahedron Letters, 1983, 24, 51.

4. Donchet, M.; Martin-Tuguy, J.; Marais, A.; Pupet, A. Phytochem, 1981, 23, 1901.

5. Shariat, M.;  Abdollahi, S.  Molecules, 2004, 9, 705-712.

6. Bain, D. I.; Smalley, R. K.  J. Chem. Soc., C 1968, 13, 1593-7.

 

Sample Availability: Available from the authors.

 

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Received: 8 March 2004 / Accepted: 18 March 2004 / Published: 1 August 2005

 

Sample Availability: Available from MDPI.

 

© 2005 MDPI. All rights reserved.