Synthesis 2016; 48(16): 2572-2580
DOI: 10.1055/s-0035-1561466
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© Georg Thieme Verlag Stuttgart · New York

Preparation of Morpholines and Benzoxazines Starting from Nitroepoxides

E. Capel
Departament de Química Inorgànica i Orgànica, Universitat Jaume I, Avda. Sos Baynat, s/n, 12071-Castelló, Spain   Email: fgonzale@uji.es
,
A. Vidal-Albalat
Departament de Química Inorgànica i Orgànica, Universitat Jaume I, Avda. Sos Baynat, s/n, 12071-Castelló, Spain   Email: fgonzale@uji.es
,
S. Rodríguez
Departament de Química Inorgànica i Orgànica, Universitat Jaume I, Avda. Sos Baynat, s/n, 12071-Castelló, Spain   Email: fgonzale@uji.es
,
F. V. González*
Departament de Química Inorgànica i Orgànica, Universitat Jaume I, Avda. Sos Baynat, s/n, 12071-Castelló, Spain   Email: fgonzale@uji.es
› Author Affiliations
Further Information

Publication History

Received: 25 April 2016

Accepted after revision: 28 April 2016

Publication Date:
16 June 2016 (online)


Abstract

Nitroepoxides are easily transformed into 2,3-disubstituted morpholines and 2,3-disubstituted benzoxazines in a two-step sequence by treatment with N-methylethanolamine and N-methyl-2-hydroxyaniline, respectively, in a highly stereoselective fashion.

Supporting Information

 
  • References

    • 1a Guo X, Chen W, Chen B, Huang W, Qi W, Zhang G, Yu Y. Org. Lett. 2015; 17: 1157
    • 1b Weiß KM, Wei S, Tsogoeva SB. Org. Biomol. Chem. 2011; 9: 3457
    • 1c Evans LA, Adams H, Barber CG, Caggiano L, Jackson RF. W. Org. Biomol. Chem. 2007; 5: 3156
    • 1d Vankar YD, Shah K, Bawa A, Singh SP. Tetrahedron 1991; 47: 8883
    • 1e Newman H, Angier RB. Tetrahedron 1970; 26: 825
    • 1f Guo X, Shao J, Liu H, Chen B, Chen W, Yu Y. RSC Adv. 2015; 5: 51559
  • 2 Vidal-Albalat A, Rodríguez S, González FV. Org. Lett. 2014; 16: 1752
  • 3 Agut J, Vidal A, Rodríguez S, González FV. J. Org. Chem. 2013; 78: 5717
  • 4 Meninno S, Napolitano L, Lattanzi A. Catal. Sci. Technol. 2015; 5: 124
    • 5a Taylor RD, MacCoss M, Lawson AD. G. J. Med. Chem. 2014; 57: 5845
    • 5b Wijtmans R, Vink MK. S, Schoemaker HE, van Delft FL, Blaauw RH, Rutjes FP. J. T. Synthesis 2004; 641
  • 6 Hajos M, Fleishaker JC, Filipiak-Reisner JK, Brown MT, Wong EH. F. CNS Drug Rev. 2004; 10: 23
  • 7 Rothman RB, Katsnelson M, Vu N, Partilla JS, Dersch CM, Blough BE, Baumann MH. Eur. J. Pharmacol. 2002; 447: 51
  • 8 Rothman RB, Baumann MH. Curr. Top. Med. Chem. 2006; 6: 1845
  • 9 Brands KM, Payack JF, Rosen JD, Nelson TD, Candelario A, Huffman MA, Zhao MW, Li J, Craig B, Song ZJ, Tschaen DM, Hansen K, Devine PN, Pye PJ, Rossen K, Dormer PG, Reamer RA, Welch CJ, Mathre DJ, Tsou NN, McNamara JM, Reider PJ. J. Am. Chem. Soc. 2003; 125: 2129
    • 10a Lai J.-Y, Shi X.-X, Gong Y.-S, Dai L.-X. J. Org. Chem. 1993; 58: 4775
    • 10b Uozumi Y, Tanahashi A, Hayashi T. J. Org. Chem. 1993; 58: 6826
    • 10c Wilkinson MC. Tetrahedron Lett. 2005; 46: 4773
    • 10d Lanman BA, Myers A. Org. Lett. 2004; 6: 1045
    • 10e Dave R, Sasaki NA. Org. Lett. 2004; 6: 15
    • 10f Pedrosa R, Andres C, Mendiguchia P, Nieto J. J. Org. Chem. 2006; 71: 8854
    • 10g Leathen ML, Rosen BR, Wolfe JP. J. Org. Chem. 2009; 74: 5107
    • 10h Chowdhury C, Mukherjee S, Das B, Achari B. J. Org. Chem. 2009; 74: 3612
    • 10i Ghorai MK, Shukla D, Das K. J. Org. Chem. 2009; 74: 7013
    • 10j Albanese D, Landini D, Penso M, Tagliabue A, Carlini E. Org. Process Res. Dev. 2010; 14: 705
    • 10k Bornholdt J, Felding J, Kristensen JL. J. Org. Chem. 2010; 75: 7454
    • 10l Ritzen B, Hoekman S, Verdasco DD, van Delft FL, Rutjes FP. J. T. J. Org. Chem. 2010; 75: 3461
    • 10m Bera S, Panda G. ACS Comb. Sci. 2012; 14: 1
    • 10n Lu Z, Stahl SS. Org. Lett. 2012; 14: 1234
    • 10o O’Reilly MC, Lindsley CW. Org. Lett. 2012; 14: 2910
    • 10p Gharpure SJ, Prasad JV. K. J. Org. Chem. 2011; 76: 10325
    • 10q Sequeira FC, Chemler SR. Org. Lett. 2012; 14: 4482
    • 10r Sun H, Huang B, Lin R, Yang C, Xia W. Beilstein J. Org. Chem. 2015; 11: 524
    • 10s Zhou L, Tan CK, Zhou J, Yeung Y.-Y. J. Am. Chem. Soc. 2010; 132: 10245
  • 11 Blattes E, Lockhart B, Lestage P, Schwendimann L, Gressens P, Fleury M.-B, Largeron M. J. Med. Chem. 2005; 48: 1282
  • 12 Rybczynski PJ, Zeck RE, Dudash JJr, Combs DW, Burris TP, Yang M, Osborne MC, Chen X, Demarest KT. J. Med. Chem. 2004; 47: 196
  • 13 Bourlot A.-S, Sánchez I, Dureng G, Guillaumet G, Massingham R, Monteil A, Winslow E, Pujol MD, Mérour J.-Y. J. Med. Chem. 1998; 41: 3142
    • 14a Hu J, Xue Y.-C, Xie M.-Y, Zhang R. J. Antibiot. 1988; 41: 1575
    • 14b Otani T, Minami Y, Marunaka T. J. Antibiot. 1988; 41: 1580
  • 15 Yang W, Wang Y, Ma Z, Golla R, Stouch T, Seethala R, Johnson S, Zhou R, Güngör T, Feyen GH. M, Dickson JK. Jr. Bioorg. Med. Chem. Lett. 2004; 14: 2327
  • 16 Su H, Su L, He Q, Zhao J, Zhao B, Zhang S, Miao J. Front. Biol. (Beijing, China) 2010; 5: 180
  • 17 Blough BE, Rothman R, Landavazo A, Page KM, Decker AM. WO 2011146850, 2011
  • 18 Allerton CM. N, Baxter AD, Cook AS, Hepworth D, Wong SK.-F. WO 200452372, 2004
  • 19 Bower JF, Szeto P, Gallagher T. Org. Lett. 2007; 9: 3283
  • 20 Deslongchamps P. Stereoelectronic Effects in Organic Chemistry . Pergamon; New York: 1983: 209-221
  • 21 Terauchi M, Abe H, Matsuda A, Shuto S. Org. Lett. 2004; 6: 3751
  • 22 Kalgutkar AS, Kozak KR, Crews BC, Hochgesang GP. Jr, Marnett LJ. J. Med. Chem. 1998; 41: 4800