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.pdfVIP
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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
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).
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