One-pot synthesis of 2-substituted 4H-3,1-benzoxazin-4-one derivatives under mild conditions using iminium cation from cyanuric chloride/dimethylformamide as a cyclizing agent

Chemistry Central Journal

Mehdi Shariat³  Mohd Wahid Samsudin²  Zuriati Zakaria¹ 

[1] Malaysia Japan International Institute of Technology, University Technology Malaysia (UTM), 54100, Kuala Lumpur, Malaysia

[2] School of Chemical Science and Food Technology, Faculty of Science and Technology, University Kebangsaan Malaysia (UKM), 43600, Selangor, Malaysia

[3] Department of Chemistry, Faculty of Science, Payame Noor University of Golpayegan (PNU), 87117-43153, Isfahan, Iran

关键词: Cyclodehydration;    Cyclizing agent;    Benzoxazinone;    Iminium cation;   

Others  :  787936
DOI  :  10.1186/1752-153X-7-58

 received in 2013-01-27, accepted in 2013-03-18,  发布年份 2013

【 摘 要 】

Background

The derivatives of 2-substituted 4H-3,1-benzoxazin-4-one belong to a significant category of heterocyclic compounds, which have shown a wide spectrum of medical and industrial applications.

Results

A new and effective one-pot method for the synthesis of 2-substituted 4H-3,1-benzoxazin-4-one derivatives is described in this paper. By using the iminium cation from a mixture of cyanuric chloride and dimethylformamide as a cyclizing agent, a series of 2-substituted 4H-3,1-benzoxazin-4-one derivatives was synthesized in high yield under mild conditions and simple workup.

Conclusions

The iminium cation from a mixture of cyanuric chloride and N,N-dimethylformamide is an effective cyclizing agent for the room temperature one-pot synthesis of 2-substituted 4H-3,1-benzoxazin-4-one derivatives in high yields through a cyclodehydration reaction. Furthermore, the method was performed under mild conditions characterized by simplified pathways and workup, minimized energy, and fewer reaction steps, compared with the previous methods. The proposed method, which is a simpler alternative than the published methods, is applicable for the synthesis of other 2-substituted 4H-3,1-benzoxazin-4-one derivatives.

【 授权许可】

   
2013 Shariat et al.; licensee Chemistry Central Ltd.

【 图 表 】

Scheme 1

Scheme 2

Scheme 3

【 参考文献 】

• [1]Peet NP, Angelastro MR, Burkhart JP: Novel orally-active elastase inhibitors. In Book Novel orally-active elastase inhibitors. Munich, Germany: European Patent Office; 1997. EP Patent 0,529,568
• [2]Colson E, Wallach J, Hauteville M: Synthesis and anti-elastase properties of 6-amino-2-phenyl-4H−3, 1-benzoxazin-4-one aminoacyl and dipeptidyl derivatives. Biochimie 2005, 87:223-230.
• [3]Oshida J, Kawabata H, Kato Y, Kokubo M, Uejima Y, Sato O, Fujii K: 4H-3, 1-benzoxazin-4-one compound and elastase inhibitor composition containing the same. Book 4H-3, 1-benzoxaz-4-one compound and elastase hibitor composition contag the same 1992. EP Patent 0,466,944
• [4]Krantz A, Spencer R, Tam T: 4H-3, 1-benzoxazin-4-ones and related compounds and use as enzyme inhibitors. In Book 4H-3, 1-benzoxaz-4-ones and related compounds and use as enzyme hibitors. U.S. Patent and Trademark Office: Washington, DC; 1987. U.S. Patent No. 4,657,893
• [5]Besson T, Rees CW, Cottenceau G, Pons AM: Antimicrobial evaluation of 3, 1-benzoxazin-4-ones, 3, 1-benzothiazin-4-ones, 4-alkoxyquinazolin-2-carbonitriles and < i > N −arylimino-1, 2, 3-dithiazoles. Bioorg Med Chem Lett 1996, 6:2343-2348.
• [6]Connolly DJ, Cusack D, O'Sullivan TP, Guiry PJ: Synthesis of quinazolinones and quinazolines. Tetrahedron 2005, 61:10153-10202.
• [7]Elgohary AMF, Hassan MM, Abass M: Synthesis of some quinazolin-4-one derivatives carrying ibuprofenyl moiety and their antiinflammatory activity. Der Pharma Chemica 2011, 3:1-12.
• [8]Azarifar D, Sheikh D: Ultrasound-Promoted Catalyst-Free Synthesis of 2,2′-(1,4-Phenylene)bis[1-acetyl-1,2-dihydro-4H-3,1-benzoxazin-4-one] Derivatives. Helv Chim Acta 2012, 95:1217-1225.
• [9]Alagarsamy V: Synthesis and pharmacological investigation of some novel 2-methyl-3-(substituted methylamino)-(3H)-quinazolin-4-ones as histamine H1-receptor blockers. Die Pharmazie - An International Journal of Pharmaceutical Sciences 2004, 59:753-755.
• [10]Kurihara M, Saito H, Nukada K, Yoda N: Cyclopolycondensation. XII. Polymerization mechanism of polybenzoxazinones in polyphosphoric acid medium. J Polym Sci [A1] 1969, 7:2897-2914.
• [11]Papadopoulos EP, Torres CD: Convenient preparation of N-substituted 2-amino-4H–3, l-benzoxazin-4-ones and 3-substituted 2,4(1H,3H)-quinazolinediones. J Heterocycl Chem 1982, 19:269-272.
• [12]Eissa AMF, El-Sayed R: Synthesis and evaluation of condensed and noncondensed heterocyclic compounds of industrial application. J Heterocycl Chem 2006, 43:1161-1168.
• [13]Anastas P, Eghbali N: Green chemistry: principles and practice. Chem Soc Rev 2010, 39:301-312.
• [14]Poliakoff M, Anastas P: Green chemistry: a principal stance. Nature 2001, 413:257-258.
• [15]Bandgar B, Pandit S: Synthesis of acyl azides from carboxylic acids using cyanuric chloride. Tetrahedron Lett 2002, 43:3413-3414.
• [16]Venkataraman K, Wagle D: Cyanuric chloride: a useful reagent for converting carboxylic acids into chlorides, esters, amides and peptides. Tetrahedron Lett 1979, 20:3037-3040.
• [17]Hamon F, Prié G, Lecornué F, Papot S: Cyanuric chloride: an efficient reagent for the Lossen rearrangement. Tetrahedron Lett 2009, 50:6800-6802.
• [18]Maia A, Albanese DCM, Landini D: Cyanuric chloride catalyzed Beckmann rearrangement of ketoximes in biodegradable ionic liquids. Tetrahedron 2012, 68:1947-1950.
• [19]Akhlaghinia B, Roohi E: Efficient method for tetrahydropyranylation of phenols and alcohols using 2, 4, 6-trichloro [1,3,5] triazine. Turk J Chem 2007, 31:83-88.
• [20]Porcheddu A, Giacomelli G, Salaris M: Microwave-assisted synthesis of isonitriles: a general simple methodology. J Org Chem 2005, 70:2361-2363.
• [21]De Luca L, Giacomelli G, Porcheddu A: A mild and efficient alternative to the classical swern oxidation. J Org Chem 2001, 66:7907-7909.
• [22]Venkataraman K, Wagle DR: Cyanuric chloride, a useful reagent for macrocyclic lactonization. Tetrahedron Lett 1980, 21:1893-1896.
• [23]Hullio AA, Mastoi GM: Application of multipurpose dimethylformamide-like task specific ionic liquid as a recyclable reagent for direct iodination of alcohols. Iranian Journal of Catalysis 2011, 1(2):79-86.
• [24]De Luca L, Giacomelli G, Porcheddu A: Beckmann rearrangement of oximes under very mild conditions. J Org Chem 2002, 67:6272-6274.
• [25]De Luca L, Giacomelli G, Porcheddu A: An efficient route to alkyl chlorides from alcohols using the complex TCT/DMF. Org Lett 2002, 4:553-555.
• [26]Thilagavathy R, Kavitha HP, Arulmozhi R, Vennila JP, Manivannan V: 2-Phenyl-4H-3,1-benzoxazin-4-one. Acta Crystallogr Sect E- Struct Rep 2009, 65:o127.
• [27]Khajavi MS, Shariat SM: A New Synthesis of 2-Substituted 4H-3,1-Benzoxazin-4-ones by Cyanuric Chloride Cyclodehydration of N-Benzoyl- and N-Acylanthranilic Acids. Heterocycles 2005, 65:1159-1165.
• [28]Bain DI, Smalley R: Synthesis of 2-substituted-4H-3, 1-benzoxazin-4-ones. J Chem Soc C 1968, 0:1593-1597.
• [29]Jagani CL, Vanparia SF, Patel TS, Dixit RB, Dixit BC: A comparative study of solution phase as well as solvent free microwave assisted syntheses of 3-benzothiazole/isoxazole substituted 2-styryl-4 (3H)-quinazolinones. Arkivoc 2012, 6:281-294.