An Efficient One-Pot Strategies for the Synthesis of [1,3] Oxazine Derivatives
2
조회
0
다운로드
0
인용
0
참고문헌
키워드
초록
Sodium hydrogen sulphate (NaHSO4), n-tetra butyl ammonium bromide (TBAB) as a phase transfer catalyst (PTC) in water, and 1-butyl-3-methyl imidazolium hydrogen sulphate [bmim]HSO4 as ionic liquid (IL) has been used as a mild reaction promoter for the cyclocondensation of formalin, β-naphthol and aromatic amines to afford respective 2,3-dihydro-2-phenyl-1H-naphtho-[1,2-e] [1,3] oxazine derivatives. The present protocols are greener, high yielding and involved the nonchromatographic isolation procedure.
Abstract
수용액 속에서 NaHSO4, TBAB (phase transfer catalyst), ionic liquid (IL) (1-butyl-3-methyl imidazolium hydrogen sulphate [bmim]HSO4)를 사용하여, formalin, β-naphthol, aromatic amines을 반응시켜서 대응하는 2,3-dihydro-2-phenyl-1Hnaphtho-[1,2-e] [1,3] oxazine 유도체를 합성할 수 있는 보다 친환경적이고, 수율이 좋고, 크로마토그래피 분리 방법을 사용하지 않는 합성 방법을 개발하였다.
참고문헌 (58)
- Meyers, A. I., , J. Org. Chem., 37, pp.4289~ (1972)
- Mayers, A. I., , J. Org. Chem., 39, pp.618~ (1974)
- Shing, O. V., , Tetrahedron Lett., 48, pp.2345~ (2007)
- Tomasulo, M., , Org. Lett., 7, pp.1109~ (2005)
- Vladmir, A. A., , Synlett, 488 (2007)
- Mehdi, G., , Synth. Commun., 38, pp.4125~ (2008)
- Zhang, P., , Bioorg. Med. Chem. Lett., 13, pp.1313~ (2003)
- Kurz, T., , Tetrahedron, 61, pp.3091~ (2005)
- Adib, M., , Tetrahedron, 62, pp.3435~ (2006)
- Zanatta, N., , J. Braz. Chem. Soc., 16, pp.1255~ (2005)
- Joyce, J. N., , J. Exp. Neurol., 184, pp.393~ (2003)
- Kerdesky, F. A. J., , Tetrahedron Lett., 46, pp.1711~ (2005)
- Cimarelli, C., , J. Org. Chem., 66, pp.4759~ (2001)
- Istvan, S., , Eur. J. Org. Chem., pp.4670~ (2006)
- Szatmari, I., , Eur. J. Org. Chem., pp.2231~ (2004)
- Zuhal, T., , Molecules, 12, pp.345~ (2007)
- Sapkal, S. B., , Green Chem. Lett. Rev., 2, pp.57~ (2009)
- Lee, J., , Bull. Korean Chem. Soc., 17, pp.115~ (1996)
- Tovar, F., , Org. Lett., 2, pp.965~ (2000)
- Kang, J. E., , Org. Lett., 8, pp.3537~ (2006)
- Palacios, F., , J. Org. Chem., 67, pp.2131~ (2002)
- Murai, T., , J. Org. Chem., 70, pp.8148~ (2005)
- Tatti, M. R., , Trans C:Chem. Chem. Eng., 16, pp.17~ (2009)
- Burke, W. J., , J. Am. Chem. Soc., 76, pp.1677~ (1954)
- Agag, J., , Appl. Poly. Sci., 100, pp.3769~ (2006)
- Domling, A., , Angew. Chem. Int. Ed., 39, pp.3168~ (2000)
- Nunes, E., , Res. J. Chem. Environ., 11, pp.90~ (2007)
- Anastas, P., , Chem. Soc. Rev., 39, pp.301~ (2010)
- Chen, J., , Green Chem., 9, pp.972~ (2007)
- Singh, P., , Tetrahedron Lett., 49, pp.727~ (2008)
- Saha, D., , Green Chem., 11, pp.733~ (2009)
- Kumar, A., , Can. J. Chem., 87, pp.714~ (2009)
- Ramesh, D., , Chem. Lett., 38, pp.586~ (2009)
- Niknam, K., , J. Chin. Chem. Soc., 56, pp.659~ (2009)
- Muthukrishnan, M., "V.G.Tetrahedron Lett.2009", Tetrahedron Lett., 50, pp.2643~ (2009)
- Khurana, J. M., , Tetrahedron Lett., 50, pp.7300~ (2009)
- Suryakant B. Sapkal, "1-Butyl-3-Methyl Imidazolium Hydrogen Sulphate Promoted One-Pot Three-Component Synthesis of Amidoalkyl Naphthols", Bulletin of the Korean Chemical Society, 30(12), pp.2887~2889 (2009), 대한화학회
- Kiran F. Shelke, "Microwave-Assisted Synthesis of 3-Styrylchromones in Alkaline Ionic Liquid", Bulletin of the Korean Chemical Society, 30(12), pp.2883~2886 (2009), 대한화학회
- Shelke, K. F., , Org. Commun., 2, pp.72~ (2009)
- Shelke, K. F., , Green Chem. Lett. Rev., 2, pp.3~ (2009)
- Li, C. J., , Chem. Soc. Rev., 35, pp.68~ (2006)
- Kumaravel, K., , Green Chem., 11, pp.1954~ (2009)
- Gu, Y., , Green Chem., 11, pp.1968~ (2009)
- Akbari, J., , Tetrahedron Lett., 50, pp.4236~ (2009)
- Zha, Z., , Green Chem., 4, pp.578~ (2002)
- Wu, J., , Chem. Commun., 16, pp.1766~ (2006)
- Beini, H. Z., , Green Chem., 11, pp.1987~ (2009)
- Khurana, J. M., , Tetrahedron Lett., 50, pp.4125~ (2009)
- Tanaka, K., , Chem. Rev., 100, pp.1025~ (2000)
- Madje, B. R., , Arkivoc, pp.82~ (2005)
- Shelke, K. F., , Cent. Eur. J. Chem., 8, pp.12~ (2010)
- Pesyan, N. N., , J. Chin. Chem. Soc., 56, pp.1018~ (2009)
- Wang, G. W., , Org. Lett., 11, pp.2385~ (2009)
- Mogilaiah, K., , Ind. J. Chem., 48B, pp.499~ (2009)
- Sapkal, S. B., , Tetrahedron Lett., 50, pp.1754~ (2009)
- Suryakant B. Sapka, "Nickel Nanoparticles: An Ecofriendly and Reusable Catalyst for the Synthesis of 3,4-Dihydropyrimidine-2(1H)-ones via Biginelli Reaction", Bulletin of the Korean Chemical Society, 31(2), pp.351~354 (2010), 대한화학회
- Kiran F. Shelke, "An Efficient Synthesis of 2,4,5-Triaryl-1H-Imidazole Derivatives Catalyzed by Boric Acid in Aqueous Media Under Ultrasound-Irradiation", Bulletin of the Korean Chemical Society, 30(5), pp.1057~1060 (2009), 대한화학회
- Shelke, K. F., , Chin. Chem. Lett., 20, pp.283~ (2009)
