Synthesis of diverse β-(nitrooxy)-substituted amines by regioselective ring-opening of aziridines under neat conditions

References

• (a) Sheldon, R. A. Green Chem. 2005, 7, 267–278;
   Google Scholar
  (b) Anastas, P. T.; Williamson, T. C. Green Chemistry: Frontiers in Benign Chemical Synthesis and Processes; University Press: London, 1998;
   Google Scholar
  (c) Loupy, A. Top. Curr. Chem. 1999, 206, 153–207;
   Web of Science ®Google Scholar
  (d) Rothenberg, G.; Downie, A. P.; Raston, C. L.; Scott, J. L. J. Am. Chem. Soc. 2001, 123, 8701–8708.
   PubMed Web of Science ®Google Scholar
• (a) Anastas, P. T.; Warner, J. C. Green Chemistry: Theory and Practice; Oxford University Press: Oxford, 1998 (2005 edition);
   Google Scholar
  (b) Sheldon, R. Nature. 1999, 399, 636–637;
   PubMed Web of Science ®Google Scholar
  (c) Tanaka, K.; Toda, F. Chem. Rev. 2000, 100, 1025–1074;
   PubMed Web of Science ®Google Scholar
  (d) Sheldon, R. A.; Hanefeld, U.; Arends, I. W. C. E. U. Green Chemistry and Catalysis; Wiley-VCH: Weinheim. 2007;
   Google Scholar
  (e) Anastas, P. T.; Levy, I. J.; Parent, K. E. (Eds.). Green Chemistry Education: Changing the Course of Chemistry. Presented at the ACS Symposium Series, Vol. 1011, American Chemical Society, USA, 2009.
   Google Scholar
• Sarkar, A.; Santra, S.; Kundu, S. K.; Hajra, A.; Zyryanov, G. V.; Chupakhin, O. N.; Charushin, V. N.; Majee, A. A Green Chem. 2016, 18, 4475–4525.
   Google Scholar
• (a) Chandrasekhar, S.; Narsihmulu, C.; Sultana, S. S. Tetrahedron Lett. 2002, 43, 7361–7363; (b) Watson, I. D. G.; Yudin, A. K. J. Org. Chem. 2003, 8, 5160–5167; (c) Hu, X. E. Tetrahedron. 2004, 60, 2701–2743; (d) Fokin, V. V.; Wu, P. Aziridine and Epoxide in Organic Synthesis; K. Wiley-VCH: Weinheim, 2006, pp 443–475; (e) Watson, I. D. G.; Yu, L.; Yudin, A. K. Acc. Chem. Res. 2006, 39, 194–206; (f) Singh, G. S.; Hooghe, M. D.; Kimpe, N. D. Chem. Rev. 2007, 107, 2080–2135; (g) Schneider, C. 2009, 121, 2116–2118. Angew. Chem. Angew. Chem., Int. Ed. 2009, 48, 2082–2084; (h) Stankovic, S.; D′Hooghe, M.; Catak, S.; Eum, H.; Waroquier, M.; Speybroeck, V. V.; Kimpe, N. D.; Ha, H.-J. Chem. Soc. Rev. 2012, 41, 643–665; (i) Ghorai, M. K.; Sahoo, A. K.; Bhattacharyya, A. J. Org. Chem. 2014, 79, 6468–6479; (j) Huang, Y.-Y.; Lv, Z.-C.; Yang, X.; Wang, Z.-L.; Zou, X.-X.; Zhao, Z.-N.; Chenb, F. Green Chem. 2017, 19, 924–927.
   Google Scholar
• (a) Matsubara, S.; Kodama, T.; Utimoto, K. Tetrahedron Lett. 1990, 31, 6379–6380; (b) Osborn, H. M. I.; Sweeney, J. B. Synlett. 1994, 145–147; (c) Meguro, M.; Asao, N.; Yamamoto, Y. Tetrahedron Lett. 1994, 35, 7395–7398; (d) Leung, W. H.; Yu, M. T.; Wu, M. C.; Yeung, L. L. Tetrahedron Lett. 1996, 37, 891–892; (e) Li, Z.; Fernandez, M.; Jacobsen, E. N. Org. Lett. 1999, 1, 1611–1613; (f) Sekar, G.; Singh, V. K. J. Org. Chem. 1999, 64, 2537–2539; (g) Chandrasekhar, M.; Sekar, G.; Singh, V. K. Tetrahedron Lett. 2000, 41, 4677–4679; (h) Chandrasekhar, M.; Sekar, G.; Singh, V. K. Tetrahedron Lett. 2000, 41, 10079–10083; (i) Sabitha, G.; Babu, S.; Rajkumar, M.; Reddy, C. S.; Yadav, J. S. Tetrahedron Lett. 2001, 42, 3955–3958; (j) Yadav, J. S.; Reddy, B. V. S.; Abraham, S.; Sabitha, G. Tetrahedron Lett. 2002, 43, 1565–1567; (k) Mita, T.; Fujimori, I.; Wada, R.; Wen, J.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2005, 127, 11252–11253; (l) Fukuta, Y.; Mita, T.; Fukuda, N.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2006, 128, 6312–6313; (m) Fujimori, I.; Mita, T.; Maki, K.; Shiro, M.; Sato, A.; Furusho, S.; Kanai, M. M.; Shibasaki, M. J. Am. Chem. Soc. 2006, 128, 16438–16439; (n) Yu, R.; Yamashita, Y.; Kobayashi, S. Adv. Synth. Catal. 2009, 351, 147–152; (o) Wu, B.; Gallucci, J. C.; Parquette, J. R.; Rajan Babu, T. V. Angew. Chem. 2009, 121, 1146–1149. Angew. Chem., Int. Ed. 2009, 48, 1126–1129; (p) Ghorai, M. K.; Kumar, A.; Tiwari, D. P. J. Org. Chem. 2010, 75, 137–151; (q) Hayashi, Y.; Kumamoto, T.; Kawahata, M.; Yamaguchi, K.; Ishikawa, T. Tetrahedron. 2010, 66, 3836–3841.
   Web of Science ®Google Scholar
• (a) Minakata, S.; Okada, Y.; Oderaotoshi, Y.; Komatsu, M. Org. Lett. 2005, 7, 3509–3512; (b) Wu, J.; Sun, X.; Xia, H.-G. Eur. J. Org. Chem. 2005, 4769–4772; (c) Wu, J.; Sun, X.; Shengqing, Y.; Sun, W. Tetrahedron Lett. 2006, 47, 4813–4816; (d) Wu, J.; Sun, X. Org. Biomol. Chem. 2006, 4, 4231–4234; (e) Matsukawa, S.; Tsukamoto, K. Org. Biomol. Chem. 2009, 7, 3792–3796; (f) Matsukawa, S.; Harada, T.; Yasuda, S. Org. Biomol. Chem. 2012, 10, 4886–4890.
   PubMed Web of Science ®Google Scholar
• (a) Bera, M.; Roy, S. J. Org. Chem. 2010, 75, 4402–4412; (b) Bera, M.; Pratihar, S.; Roy, S. J. Org. Chem. 2011, 76, 1475–1478; (c) Huang, C.-Y.; Doyle, A. G. J. Am. Chem. Soc. 2012, 134, 9541–9544; (d) Nielsen, D. K.; Huang, C.-Y.; Doyle, A. G. J. Am. Chem. Soc. 2013, 135, 13605–13609; (e) Duda, M. L.; Michael, F. E. J. Am. Chem. Soc. 2013, 135, 18347–18349; (f) Sayyad, M.; Nanaji, Y.; Ghorai, M. K. J. Org. Chem. 2015, 80, 12659–12667.
   PubMed Web of Science ®Google Scholar
• (a) Wu, J.; Hou, X.-L.; Dai, L.-X. J. Org. Chem. 2000, 65, 1344–1348; (b) Tang, C.-Y.; Wang, G.; Yang, X.-Y.; Wu, X.-Y.; Sha, F. Tetrahedron Lett. 2014, 55, 6447–6450.
   PubMed Web of Science ®Google Scholar
• (a) Das, B.; Krishnaiah, M.; Venkateswarlu, K. Tetrahedron Lett. 2006, 47, 6027–6029; (b) Das, B.; Krishnaiah, M.; Venkateswarlu, K.; Reddy, V. S. Helv. Chim. Acta. 2007, 90, 110–113; (c) Volkova, Y. A.; Averina, E. B.; Kuznetsova, T. S.; Zefirov, N. S. Tetrahedron Lett. 2010, 51, 2254–2257.
   Web of Science ®Google Scholar
• (a) Needleman P. (Ed.), Organic Nitrates; Springer-Verlag Berlin: Heidelberg, 1975;
   Google Scholar
  (b) U. Abshagen (Ed.). Clinical Pharmacology of Antianginal Drugs; Springer-Verlag: Berlin, Heidelberg, 1985.
   Google Scholar
• Liu, Z.-Q.; Fan, Y.; Li, R.; Zhou, B.; Wu, L.-M. Tetrahedron Lett. 2005, 46, 1023–1025.
   Web of Science ®Google Scholar
• (a) Ghosal, N. C.; Santra, S.; Das, S.; Hajra, A.; Zyryanov, G. V.; Majee, A. Green Chem. 2016, 18, 565–574; (b) Ghosal, N.; Mahato, S.; Chatterjee, R.; Santra, S.; Zyryanov, G.; Majee, A. SynOpen. 2017, 1, 0015–0023.
   Google Scholar
• Ghosal, N. C.; Santra, S.; Zyryanov, G. V.; Hajra, A.; Majee, A. Tetrahedron Lett. 2016, 57, 3551–3555.
   Web of Science ®Google Scholar
• Further information can be found in the CIF file. This crystal was deposited in the Cambridge Crystallographic Data Centre and assigned as CCDC 1549293.
   Google Scholar
• (a) Bergmeier, S. C. Tetrahedron. 2000, 56, 2561–2576;
   Web of Science ®Google Scholar
  (b) Donohoe, T. J.; Callens, C. K. A.; Flores, A.; Lacy, A. R.; Rathi, A. H. Chem. Eur. J. 2011, 17, 58–76.
   PubMed Web of Science ®Google Scholar
• (a) Bergmeier, S. C.; Stanchina, D. M. J. Org. Chem. 1999, 64, 2852–2859; (b) Kakeya, H.; Morishita, M.; Kobinata, M.; Osono, M.; Ishizuka, M.; Osada, H. J. Antibiot. 1998, 51, 1126–1128.
   PubMed Web of Science ®Google Scholar
• Thakur, V. V.; Sudalai, A. Tetrahedron Lett. 2003, 44, 989–992.
   Web of Science ®Google Scholar