Research on the Reaction of 5-Alkyloxy-3,4-dihalo-2(5H)- furanones with Aliphatic Amines

doi:10.6023/cjoc1106302

Chin. J. Org. Chem. ›› 2012, Vol. 32 ›› Issue (01): 104-112.DOI: 10.6023/cjoc1106302 Previous Articles Next Articles

Articles

5-烷氧基-3,4-二卤-2(5H)-呋喃酮与脂肪胺类的反应研究

傅建花, 汪朝阳, 霍景沛, 谭越河, 曾荣华

华南师范大学化学与环境学院广州 510006

收稿日期:2011-06-30 修回日期:2011-08-29 发布日期:2011-09-21
通讯作者: 汪朝阳 E-mail:wangwangzhaoyang@tom.com
基金资助:
国家自然科学基金(No. 20772035)、广东省自然科学基金(No. 5300082)及广东省高等学校人才引进专项基金(No. [2011]431)资助项目.

Research on the Reaction of 5-Alkyloxy-3,4-dihalo-2(5H)- furanones with Aliphatic Amines

Fu Jianhua, Wang Zhaoyang, Huo Jingpei, Tan Yuehe, Zeng Ronghua

School of Chemistry and Environment, South China Normal University, Guangzhou 510006

Received:2011-06-30 Revised:2011-08-29 Published:2011-09-21
Contact: Zhaoyang Wang E-mail:wangwangzhaoyang@tom.com
Supported by:
Project supported by the the National Natural Science Foundation of China (No. 20772035), the Natural Science of Foundation of Guangdong Provine (No. 5300082) and the 3rd Talents Special Funds of Guangdong Higher Education (No. [2011]431).

Using KF as catalyst and tetrahydrofuran as solvent, 5-alkyloxy-3,4-dihalo-2(5H)-furanones was reacted with several aliphatic amines. The chemical structures and absolute configurations of the products were confirmed via rotation, UV-Vis, IR, ¹H NMR, ¹³C NMR, MS techniques, elemental analysis and X-ray single crystal diffraction. Thirteen new normal products β-amino-2(5H)-furanones were obtained via the tandem Michael addition-elimination reaction as anticipated in most cases. However, the reaction between the larger steric dicyclohexyl amine and 5-alkyloxy-3,4-dihalo-2(5H)-furanones yielded four new abnormal products, (E)-alkyl 2-halo-4-dicyclohexylamino-4-oxobut-2-enoate. The possible mechanism for the formation of 2(5H)-furanone ring-opening products involving in the rearrangement reaction was proposed.

Key words: 5-alkoxy-3,4-dihalo-2(5H)-furanone, aliphatic saturated secondary amine, tandem Michael addition-elinmination reaction, β-amino-2(5H)-furanone, ring-opening rearrangement reaction

Cite this article

Fu Jianhua, Wang Zhaoyang, Huo Jingpei, Tan Yuehe, Zeng Ronghua . Research on the Reaction of 5-Alkyloxy-3,4-dihalo-2(5H)- furanones with Aliphatic Amines[J]. Chin. J. Org. Chem., 2012, 32(01): 104-112.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Juan, H. V. E.; Saad, J. R.; Giordano, O. S.; Garcia, C.; Martin, T.; Martin, V. S.; Sosa, M. E.; Tonn, C. E. J. Nat. Prod. 2008, 71, 190.

[2] Wei, M.-X.; Feng, L.; Li, X.-Q.; Zhou, X.-Z.; Shao, Z.-H. Eur. J. Med. Chem. 2009, 44, 3340.

[3] Pimentel-Elardo, S. M.; Kozytska, S.; Bugni, T. S.; Ireland, C. M.; Moll, H.; Hentschel, U. Mar. Drugs 2010, 8, 373.

[4] Prasad, K. R.; Gandi, V. R. Tetrahedron: Asymmetry 2010, 21, 275.

[5] Lattmann, E.; Billington, D. C.; Langley, C. A. Drug Des. Discovery. 1999, 16, 243.

[6] Arayarat, P.; Singh, H.; Lattmann, E. Sci. Asia 2001, 27, 121.

[7] Lattmann, E.; Dunn, S.; Niamsanit, S.; Sattayasai, N. Bioorg. Med. Chem. Lett. 2005, 15, 919.

[8] Lattmann, E.; Sattayasai, N.; Schwalbe, C. S.; Niamsanit, S.; Billington, D. C.; Lattmann, P.; Langley, C. A.; Singh. H.; Dunn, S. Curr. Drug Discovery Technol. 2006, 3, 125.

[9] Tanoury, G. J.; Chen, M.; Dong, Y.; Forslund, R. E.; Magdziak, D. Org. Lett. 2008, 10, 185.

[10] Yu, Z.-L.; Hu, S.-Q.; Li, S.-L.; Fu, Y-Q. Chin. J. Org. Chem. 2008, 28, 1119 (in Chinese). (郁兆莲, 胡少强, 李森兰, 傅玉琴, 有机化学, 2008, 28, 1119.)

[11] Song, X.-M.; Wang, Z.-Y.; Li, J.-X.; Fu, J.-H. Chin. J. Org. Chem. 2009, 29, 1804 (in Chinese). (宋秀美, 汪朝阳, 李建晓, 傅建花, 有机化学, 2009, 29, 1804.)

[12] Mo, Y.-Q.; Wang, Z.-Y.; Li, J.-X.; Hong, W.-K. Chin. J. Org. Chem. 2010, 30, 1051 (in Chinese). (莫阳青, 汪朝阳, 李建晓, 洪文坤, 有机化学, 2010, 30, 1051.)

[13] Song, X.-M.; Tan, Y.-H.; Li, J.-X.; Wang, Z.-Y. Chin. J. Org. Chem. 2010, 30, 1890 (in Chinese). (宋秀美, 谭越河, 李建晓, 汪朝阳, 有机化学, 2010, 30, 1890.)

[14] Lattmann, E.; Lattmann, P.; Singh, H. WO 2004106315, 2004[Chem. Abstr. 2005, 142, 38133].

[15] Chen, Q.-H.; Geng, Z.; Huang, B. Tetrahedron: Asymmetry 1995, 6, 401.

[16] Kurbangalieva, A. R.; Devyatova, N. F.; Bogdanov, A. V.; Berdnikov, E. A.; Mannafov, T. G.; Krivolapov, D. B.; Litvinov, I. A.; Chmutova, G. A. Phosphorus, Sulfur Silicon Relat. Elem. 2007, 182, 607.

[17] Devyatova, N. F.; Kosolapova, L. S.; Kurbangalieva, A. R.;Berdnikov, E. A.; Lodochnikova, O. A.; Litvinov, I. A.; Chmutova, G. A. Russ. J. Org. Chem. 2008, 44, 1225.

[18] Kurbangalieva, A. R.; Devyatova, N. F.; Kosolapova, L. S.; Lodochnikova, O. A.; Berdnikov, E. A.; Litvinov, I. A.; Chmutova, G. A. Russ. Chem. Bull. 2009, 58, 126.

[19] Polezhaeva, N. A.; Volodina, Yu. M.; Kalinina, I. V.; Sakhibullina, V. G.; Chmutova, G. A.; Galkin, V. I.; Cherkasov, R. A. Russ. J. Gen. Chem. 2002, 72, 1202.

[20] Kurbangalieva, A. R.; Bogdanov, A. V.; Movchan, A. I.; Chmutova, G. A. Russ. J. Org. Chem. 2004, 40, 1216.

[21] Teitei, T. Aust. J. Chem. 1986, 39, 503.

[22] Mellor, J. M.; Wagland, A. M. J. Chem. Soc., Perkin Trans. 1 1989, 997.

[23] Dawson, J. R.; Mellor, J. M. Tetrahedron Lett. 1995, 36, 9043.

[24] Beccalli, E. M.; Marchesini, A. Tetrahedron 1995, 51, 2353.

[25] Hashmi, A. S. K.; Grundl, M. A.; Nass, A. R.; Naumann, F.; Bats, J. W.; Bolte, M. Eur. J. Org. Chem. 2001, 4705.

[26] Iyer, V. K.; Horwitz, J. P. J. Org. Chem. 1982, 47, 644.

[27] Morlender-Vais, N.; Mandelbaum. A. J. Mass Spectrom. 1999, 34, 637.

[28] Xu, Y.; Zhu, S. Z. Tetrahedron 2001, 57, 3909.

[29] Abe, M.; Hattori, M.; Takegami, A.; Masuyama, A.; Hayashi, T.; Seki, S.; Tagawa, S. J. Am. Chem. Soc. 2006, 128, 8008.

[30] Briehl, H.; Lukosch, A.; Wentrup C. J. Org. Chem. 1984, 49, 2772.

[31] Rickborn, B. Org. React. 1998, 52.

[32] Bibas, H.; Moloney, D. W. J.; Neumann, R.; Shtaiwi, M.; Bernhardt, P. V.; Wentrup, C. J. Org. Chem. 2002, 67, 2619.

[33] Chiang, Y.; Gaplovsky, M.; Kresge, A. J.; Leung, K. H.; Ley, C.; Mac, M.; Persy, G.; Phillips, D. L.; Popik, V. V.; Roedig, C.; Wirz, J.; Zhu, Y. J. Am. Chem. Soc. 2003, 125, 12872.

[34] Finnerty J. J.; Wentrup C. J. Org. Chem. 2004, 69, 1909.

[35] Halton, B.; Dixon, G. M.; Jones, C. S.; Parkin, C. T.; Veedu, R. N.; Bornemann, H.; Wentrup, C. Org. Lett. 2005, 7, 949.

[36] Veedu, R. N.; Kokas, O. J.; Couturier-Tamburelli, I.; Koch, R.; Aycard, J.-P.; Borget, F.; Wentrup, C. J. Phys. Chem. A 2008, 112, 9742.

[37] Fulloon, B. E.; Wentrup, C. Aust. J. Chem. 2009, 62, 115.

[38] Alvarez, M. A.; García, M. E.; Martínez, M. E.; Menéndez, S.; Ruiz, M. A. Organometallics 2010, 29, 710.

5-烷氧基-3,4-二卤-2(5H)-呋喃酮与脂肪胺类的反应研究

Research on the Reaction of 5-Alkyloxy-3,4-dihalo-2(5H)- furanones with Aliphatic Amines

PDF

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 1

Recommended Articles

Metrics

Comments