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Synthesis 2017; 49(09): 1955-1968
DOI: 10.1055/s-0036-1588748
DOI: 10.1055/s-0036-1588748
feature
Metal-Free Synthesis of Oxazinones and Their Reductive Ring Opening to Provide Cyclopropyl Carbinols
Weitere Informationen
Publikationsverlauf
Received: 03. Februar 2017
Accepted after revision: 23. Februar 2017
Publikationsdatum:
14. März 2017 (online)
Abstract
General routes for the synthesis of 1,3-oxazin-4-ones are discussed, with particular attention paid to recent developments in the field. The syntheses of amine functionalised cyclopropyl carbinols via a hydride-mediated reduction of various 5-chloroethyl-1,3-oxazin-4-enones in moderate to good yield are disclosed. This new method provides an opportunity to access greater structural diversity within these useful synthetic building blocks.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588748.
- Supporting Information
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References
- 1 Vitaku E, Smith DT, Njardarson JT. J. Med. Chem. 2014; 57: 10257
- 2 Basmajian JV, Shankardass K, Russell D, Yucel V. Arch. Phys. Med. Rehabil. 1984; 65: 698
- 3 Moreno L, Cabedo N, Boulangé A, Párraga J, Galán A, Leleu S, Sanz M.-J, Cortes D, Franck X. Eur. J. Med. Chem. 2013; 69: 69
- 4 Basappa, Murugan S, Kavitha CV, Purushothaman A, Nevin KG, Sugahara K, Rangappa KS. Cancer Lett. 2010; 297: 231
- 5 Hossan A, Abu-Melha H, Al-Omar M, Amr A. Molecules 2012; 17: 13642
- 6 Loughlin WA, Tyndall JD. A, Glenn MP, Hill TA, Fairlie DP. Chem. Rev. 2010; 110: PR32
- 7 Sato M, Ogasawara H, Kato T. Chem. Pharm. Bull. 1984; 32: 2602
- 8 Panunzio M, Tamanini E, Bandini E, Campana E, D’Aurizio A, Vicennati P. Tetrahedron 2006; 62: 12270
- 9 May AE, Hoye TR. J. Org. Chem. 2010; 75: 6054
- 10 Moazami Y, Pierce JG. Synthesis 2015; 47: 3363
- 11 Zhang Y, Ji J, Zhang X, Lin S, Pan Q, Jia L. Org. Lett. 2014; 16: 2130
- 12 Liu L, Sun H. Angew. Chem. Int. Ed. 2014; 53: 9865
- 13 O’Donnell MJ, Craig AJ, Hawkins BC. Ethyl N-(Diphenylmethylene)glycinate. In e-EROS Encyclopedia of Reagents for Organic Synthesis. Wiley; New York: 2001
- 14 Craig AJ, van der Salm L, Stevens-Cullinane L, Lucas NT, Tan EW, Hawkins BC. Org. Lett. 2015; 17: 234
- 15 Smith RJ, Mills DA, Nhu D, Tan EW, Lucas NT, Hawkins BC. J. Org. Chem. 2016; 81: 2099
- 16 Andrés C, Nieto J, Pedrosa R, Villamañán N. J. Org. Chem. 1996; 61: 4130
- 17 Martin TJ, Rovis T. Angew. Chem. Int. Ed. 2013; 52: 5368
MissingFormLabel
- 18 Cheng G, Wang X, Su D, Liu H, Liu F, Hu Y. J. Org. Chem. 2010; 75: 1911
- 19 Dufresne C, Young K, Pelaez F, Gonzalez Del Val A, Valentino D, Graham A, Platas G, Bernard A, Zink D. J. Nat. Prod. 1997; 60: 188
- 20 Kelner MJ, McMorris TC, Beck WT, Zamora JM, Taetle R. Cancer Res. 1987; 47: 3186
- 21 Anchel M, Hervey A, Robbins WJ. Proc. Natl. Acad. Sci. U.S.A. 1952; 38: 927
- 22 Kokubun T, Scott-Brown A, Kite GC, Simmonds MS. J. J. Nat. Prod. 2016; 79: 1698
- 23 Chen J.-Y, Li P.-L, Tang X.-L, Wang S.-J, Jiang Y.-T, Shen L, Xu B.-M, Shao Y.-L, Li G.-Q. J. Nat. Prod. 2014; 77: 1997
- 24 Liu Z, Chen Y, Chen S, Liu Y, Lu Y, Chen D, Lin Y, Huang X, She Z. Org. Lett. 2016; 18: 1406
- 25 Kusama H, Hara R, Kawahara S, Nishimori T, Kashima H, Nakamura N, Morihira K, Kuwajima I. J. Am. Chem. Soc. 2000; 122: 3811
- 26 Bertinato P, Sorensen EJ, Meng D, Danishefsky SJ. J. Org. Chem. 1996; 61: 8000
- 27 Balog A, Meng D, Kamenecka T, Bertinato P, Su D.-S, Sorensen EJ, Danishefsky SJ. Angew. Chem., Int. Ed. Engl. 1996; 35: 2801
- 28 Sandridge MJ, France S. Org. Lett. 2016; 18: 4218
- 29 Kothandaraman P, Huang C, Susanti D, Rao W, Chan PW. H. Chem. Eur. J. 2011; 17: 10081
- 30 Li P.-F, Yi C.-B, Qu J. Org. Biomol. Chem. 2015; 13: 5012
- 31 Ranu BC, Banerjee S. Eur. J. Org. Chem. 2006; 3012
- 32 Rao W, Zhang X, Sze EM. L, Chan PW. H. J. Org. Chem. 2009; 74: 1740
- 33 Yamauchi Y, Onodera G, Sakata K, Yuki M, Miyake Y, Uemura S, Nishibayashi Y. J. Am. Chem. Soc. 2007; 129: 5175
- 34 Enholm EJ, Jia ZJ. J. Org. Chem. 1997; 62: 9159
- 35 Xiao H.-q, Shu X.-z, Ji K.-g, Qi C.-z, Liang Y.-m. New J. Chem. 2007; 31: 2041
- 36 Masui M, Shioiri T. Synlett 1997; 273
- 37 Dwivedi N, Tewari N, Tiwari VK, Chaturvedi V, Manju YK, Srivastava A, Giakwad A, Sinha S, Tripathi RP. Bioorg. Med. Chem. Lett. 2005; 15: 4526
- 38 Singh C, Pandey S, Saxena G, Srivastava N, Sharma M. J. Org. Chem. 2006; 71: 9057
- 39 Bietti M, Gente G, Salamone M. J. Org. Chem. 2005; 70: 6820
- 40 Mothe SR, Kothandaraman P, Rao W, Chan PW. H. J. Org. Chem. 2011; 76: 2521
- 41 Chan PW. H, Teo WT, Koh SW. Y, Lee BR, Ayers BJ, Ma D.-L, Leung C.-H. Eur. J. Org. Chem. 2015; 4447
- 42 Li Q, Jiang G.-J, Jiao L, Yu Z.-X. Org. Lett. 2010; 12: 1332
MissingFormLabel
- 43 Wang H.-Y, Yang K, Bennett SR, Guo S.-r, Tang W. Angew. Chem. Int. Ed. 2015; 54: 8756
- 44 Paquette LA, Crouse GD, Sharma AK. J. Am. Chem. Soc. 1982; 104: 4411
- 45 Hardouin C, Taran F, Doris E. J. Org. Chem. 2001; 66: 4450
- 46 Mothe SR, Chan PW. H. J. Org. Chem. 2009; 74: 5887
- 47 Padwa A, Hornbuckle SF, Fryxell GE, Zhang ZJ. J. Org. Chem. 1992; 57: 5747
- 48 Albert J, Cadena JM, Granell J, Solans X, Font-Bardia M. J. Organomet. Chem. 2004; 689: 4889
- 49 Jia Z, Wei S, Zhu Q. Biol. Pharm. Bull. 2010; 33: 725
- 50 Hinman RL, Hamm KL. J. Org. Chem. 1958; 23: 529
- 51 Seuyep Ntoukam DH, Luinstra GA, Theato P. J. Polym. Sci., Part A: Polym. Chem. 2014; 52: 2841