synthesis of 4h-3,1-benzoxazin-4-one 2-phenyl using cyanuric chloride as a cyclization agent合成4 h-3 1-benzoxazin-4-one 2-phenyl使用氰尿酰氯作为环化剂.pdf

Molbank 2004 Molbank 2005, M448 /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 email: sohrab202020@ 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 [14]. The synthesis of benzoxazinone derivative, 4H3,1benzoxazin4one 2(Nphthaloylmethyl), was reported previously by our team [5]. In this paper we have used the same method to synthesize 4H3,1benzoxazin4one 2phenyl 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: 1 HNMR (CDCl ): δ= 7.109.13 (m, 9H, ArH; NH); 12.112.3 (broad singlet,COOH).