Synthesis of Benzo[b][1,4]oxazine-2-amines via the Multicomponent Reaction between Benzyl Alcohol, 2-aminophenol, and Isocyanide by Using Urea Hydrogen Peroxide in the Presence of Magnesium Bromide Catalyst

Document Type : Research Article

Authors

Department of Chemistry, Razi University, Kermanshah, I.R. IRAN

Abstract

A three-component reaction between the derivatives of benzyl alcohol, 2-aminophenol, and isocyanide for preparation Benzo[b][1,4]oxazine-2-amine derivatives has been reported. In this reaction, benzaldehyde derivatives were obtained as in situ from benzyl alcohol under oxidation by in urea hydrogen peroxide and magnesium bromide catalyst. This reaction was preferred in High efficiency and easy separation products of the reaction conditions. 

Keywords

Main Subjects

References

[1] Hudlicky T., Luna H., Price J.D., Rulin F., Microbial Oxidation of Chloroaromatics in the Enantiodivergent Synthesis of Pyrrolizidine Alkaloids: Trihydroxyheliotridanes, J. Org.Chem., 55: 4683-4687 (1990).
[2] Chaudhari, M.P., Sawant, S.B., Kinetics of Heterogeneous Oxidation of Benzyl Alcohol with Hydrogen peroxide, Chem. Eng. J., 106: 111-118 (2005).
[3] March J., “Advanced Organic Chemistry: Reactions, Mechanisms, and Structure”, John Wiley & Sons, NewYork, (1992).
[4] Marko I.E., Giles P.R., Tsukazaki M., Brown S.M., Urch C.J., Copper-Catalyzed Oxidation of Alcohols to Aldehydes and Ketones: An Efficient, Aerobic Alternative, Science, 274:  2044-2046 (1996).
[5] Sheldon R.A., Kochi J.K., “Metal-Catalyzed Oxidations of Organic Compounds”, Academic Press, New York, (1981).
[6] Damavandi J., Karami A.B., Zolfigol M.A., Selective Oxidation of N-Alkyl Imines to Oxaziridines Using UHP/Maleic Anhydride System, Synlett, 933: (2002).
[7] Zhu J., Bienaymé H., “Multicomponent Reactions”, Wiley-VCH: Weinheim, (2005).
[8] Domling A., Recent Developments in Isocyanide Based Multicomponent Reactions in Applied Chemistry, Chem. Rev., 106: 17-89 (2006).
[9] Ugi I., Werner B., Dömling A., The Chemistry of Isocyanides, their MultiComponent Reactions and their Libraries, Molecules, 8: 53-66 (2003).
[10] تیموری، محمد باقر؛ باژرنگ، ریحانه؛ به دام اندازی حدواسط هویزگن به دست آمده از واکنش ایزوسیانیدها با آلکین‌های فعال: روشی کارآمد برای سنتز ترکیبات آلی نوین، نشریهشیمیومهندسیشیمیایران، (3) 29: 1 تا 28 (1389).
[11] Fringuelli R., Pietrella D., Schiaffella F., Guarrac I.A., Perito S., Bistoni F., Vecchiarelli A., Anti-Candida Albicans Properties of Novel Benzoxazine Analogues, Bioorg. Med. Chem., 10: 1681-1686 (2002).
[12] Macchiarulo A., Costantino G., Fringuelli F., Vecchiarelli A., Schiaffella F., Fringuelli, R., 1,4-Benzothiazine and 1,4-Benzoxazine Imidazole Derivatives with Antifungal Activity: A Docking Study, Bioorg. Med. Chem., 10: 3415-3423 (2002).
[13] Adams N.D., Darcy M.G., Dhanak D., Duffy K.J., Fitch D.M., Knight S.D., Newlander K.A., Shaw A.N., Int. Patent, WO 2006113432, (2006).
[14] Soleimani E., Zainali M.,Isocyanide-Based Multicomponent Reactions: Synthesis of Alkyl-2-(1-(alkylcarbamoyl)-2,2-dicyanoethyl)benzoate and Isochromeno[3,4-b]pyrrole Derivatives, J. Org. Chem.,76: 10306-10311 (2011).
[15] Soleimani E., Zainali M., Samadi S., Isocyanide-Based Multicomponent Reactions: Synthesis of 3,3-dicyano-N-alkyl-2-arylpropanamide Derivatives, Tetrahedron Lett., 52: 4186-4188 (2011).
[16] Soleimani E., Zainali M., Ghasemi N., Notash B., Isocyanide-based Multicomponent Reactions: Synthesis of 2-(1-(alkylcarbamoyl)-2,2-dicyanoethyl)-N-alkylbenzamide and 1,7-diazaspiro[4,4]nonane-2,4-dione Derivatives, Tetrahedron, 69:  9832- (2013).
[17] Soleimani E., Ghorbani S., Ghasempour H.R., Novel Isocyanide-Based Three-Component Reaction: A Facile Synthesis of Substituted 1H-chromeno[2,3-d]pyrimidine-5-carboxamides, Tetrahedron, 69: 8511-8515 (2013).
[18] Soleimani E., Khodaei M.M., Taheri Kal Koshvandi A., Three-Component, One-Pot Synthesis of Benzo[b][1,4]oxazines in Ionic Liquid 1-Butyl-3-methylimidazolium Bromide, Synth. Commun. 42: 1367-1371 (2012).
[19] Heravi M.M., Baghernejad B., Oskooie H.A., A Novel Three-Component Reaction for the Synthesis of 3-aryl-4H-benzo [1,4] Oxazin-2-amine, Mol. Divers., 13: 395-398 (2009).
[20] Wasserscheid P., Keim W., Ionic Liquids—New “Solutions” for Transition Metal Catalysis, Angew. Chem. Int. Ed., 39: 3772-3789 (2000).
[21] Welton T., Ionic Liquids in Catalysis, Coord. Chem. Rev., 248: 2459-2477 (2004).
[22] Sheldon R.A., Madeira R., Lau R.M., Sorgedrager M.J., van Rantwijk F., Seddon K.R., Biocatalysis in ionic liquids, Green. Chem., 4: 147-151 (2002).

Files

Share

How to cite

Statistics