2,2,2-Trifluroenthanol promoted synthesis of unsymmetrical ureas from dioxazolones and amines via tandem lossen rearrangement/condensation process

References

• (a) Bégué, J.-P.; Bonnet-Delpon, D.; Crousse, B. Synlett. 2004, 1, 18.
   Google Scholar
  (b) Shuklov, I. A.; Dubrovina, N. V.; Börner, A. Synthesis. 2007, 2007, 2925–2943. DOI: https://doi.org/10.1055/s-2007-983902.
   Google Scholar
  (c) Dohi, T.; Yamaoka, N.; Kita, Y. Tetrahedron. 2010, 66, 5775–5785. DOI: https://doi.org/10.1016/j.tet.2010.04.116.
   Web of Science ®Google Scholar
  (d) Sugiishi, T.; Matsugi, M.; Hamamoto, H.; Amii, H. RSC Adv. 2015, 5, 17269–17282. DOI: https://doi.org/10.1039/C4RA11860J.
   Web of Science ®Google Scholar
  (e) Wencel-Delord, J.; Colobert, F. Org. Chem. Front. 2016, 3, 394–400. DOI: https://doi.org/10.1039/C5QO00398A.
   Web of Science ®Google Scholar
  (f) Colomer, I.; Chamberlain, A. E. R.; Haughey, M. B.; Donohoe, T. J. Nat. Rev. Chem. 2017, 1, 0088. DOI: https://doi.org/10.1038/s41570-017-0088.
   Web of Science ®Google Scholar
  (g) An, X.-D.; Xiao, J. Chem. Rec. 2020, 20, 142–161. DOI: https://doi.org/10.1002/tcr.201900020.
   PubMed Web of Science ®Google Scholar
  (h) Bhattacharya, T.; Ghosh, A.; Maiti, D. Chem. Sci. 2021, 12, 3857–3870. DOI: https://doi.org/10.1039/d0sc06937j.
   PubMed Web of Science ®Google Scholar
• (a) Podolin, P. L.; Bolognese, B. J.; Foley, J. J.; Schmidt, D. B.; Buckley, P. T.; Widdowson, K. L.; Jin, Q.; White, J. R.; Lee, J. M.; Goodman, R. B.; et al. J. Immunol. 2002, 169, 6435–6444. DOI: https://doi.org/10.4049/jimmunol.169.11.6435.
   PubMed Web of Science ®Google Scholar
  (b) Bloom, J. D.; DiGrandi, M. J.; Dushin, R. G.; Curran, K. J.; Ross, A. A.; Norton, E. B.; Terefenko, E.; Jones, T. R.; Feld, B.; Lang, S. A. Bioorg. Med. Chem. Lett. 2003, 13, 2929–2932. DOI: https://doi.org/10.1016/S0960-894X(03)00586-9.
   PubMed Web of Science ®Google Scholar
  (c) Häcker, H.-G.; Leyers, S.; Wiendlocha, J.; Gütschow, M.; Wiese, M. J. Med. Chem. 2009, 52, 4586–4595. DOI: https://doi.org/10.1021/jm900688v.
   PubMed Web of Science ®Google Scholar
  (d) Kaufmann, D.; Bialer, M.; Shimshoni, J. A.; Devor, M.; Yagen, B. J. Med. Chem. 2009, 52, 7236–7248. DOI: https://doi.org/10.1021/jm901229s.
   PubMed Web of Science ®Google Scholar
  (e) Sharma, S. K.; Wu, Y.; Steinbergs, N.; Crowley, M. L.; Hanson, A. S.; Casero, R. A.; Jr.; Woster, P. M. J. Med. Chem. 2010, 53, 5197–5212. DOI: https://doi.org/10.1021/jm100217a.
   PubMed Web of Science ®Google Scholar
• (a) Mahrwald, R. Enantioselective Organocatalyzed Reactions, Springer: New York, 2011.
   Google Scholar
  (b) Dalko, P. I. Comprehensive Enantioselective Organocatalysis: Catalysts, Reactions, and Applications, Wiley-VCH: Weinheim, 2013.
   Google Scholar
  (c) Zhang, Z.; Schreiner, P. R. Chem. Soc. Rev. 2009, 38, 1187–1198. DOI: https://doi.org/10.1039/b801793j.
   PubMed Web of Science ®Google Scholar
  (d) Fanourakis, A.; Docherty, P. J.; Chuentragool, P.; Phipps, R. J. ACS Catal. 2020, 10, 10672–10714. DOI: https://doi.org/10.1021/acscatal.0c02957.
   PubMed Web of Science ®Google Scholar
  (e) Zhao, Q.; Chen, C.; Wen, J.; Dong, X.-Q.; Zhang, X. Acc. Chem. Res. 2020, 53, 1905–1921. DOI: https://doi.org/10.1021/acs.accounts.0c00347.
   PubMed Web of Science ®Google Scholar
  (f) Imperato, G.; Eibler, E.; Niedermaier, J.; König, B. Chem. Commun. 2005, 9, 1170–1172. DOI: https://doi.org/10.1039/B414515A.
   PubMed Web of Science ®Google Scholar
  (g) Imperato, G.; Höger, S.; Lenoir, D.; König, B. Green Chem. 2006, 8, 1051–1055. DOI: https://doi.org/10.1039/B603660K.
   Web of Science ®Google Scholar
  (h) Gore, S.; Baskaran, S.; Koenig, B. Green Chem. 2011, 13, 1009. DOI: https://doi.org/10.1039/c1gc00009h.
   Web of Science ®Google Scholar
  (i) Xia, Z.; Hu, J.; Gao, Y.-Q.; Yao, Q.; Xie, W. Chem. Commun. 2017, 53, 7485–7488. DOI: https://doi.org/10.1039/c7cc03754f.
   PubMed Web of Science ®Google Scholar
• (a) Camp, J. E.; Mistry, L.; Mapesa, K.; Bousfield, T. W. Green Chem. 2017, 19, 2123–2128. DOI: https://doi.org/10.1039/C7GC00908A.
   Web of Science ®Google Scholar
  (b) Barrett, A. G. M.; Boorman, T. C.; Crimmin, M. R.; Hill, M. S.; Kociok-Köhn, G.; Procopiou, P. A. Chem. Commun. 2008, 41, 5206. DOI: https://doi.org/10.1039/b809649j.
   Google Scholar
  (c) Hernán-Gómez, A.; Bradley, T. D.; Kennedy, A. R.; Livingstone, Z.; Robertson, S. D.; Hevia, E. Chem. Commun. 2013, 49, 8659–8661. DOI: https://doi.org/10.1039/c3cc45167d.
   PubMed Web of Science ®Google Scholar
  (d) Bhattacharjee, J.; Das, S.; Kottalanka, R. K.; Panda, T. K. Dalton Trans. 2016, 45, 17824–17832. DOI: https://doi.org/10.1039/c6dt03063g.
   PubMed Web of Science ®Google Scholar
  (e) Naktode, K.; Das, S.; Bhattacharjee, J.; Nayek, H. P.; Panda, T. K. Inorg. Chem. 2016, 55, 1142–1153. DOI: https://doi.org/10.1021/acs.inorgchem.5b02302.
   PubMed Web of Science ®Google Scholar
  (f) South, A. J.; Geer, A. M.; Taylor, L. J.; Sharpe, H. R.; Lewis, W.; Blake, A. J.; Kays, D. L. Organometallics. 2019, 38, 4115–4120. DOI: https://doi.org/10.1021/acs.organomet.9b00393.
   Web of Science ®Google Scholar
  (g) Karmel, I. S.; Tamm, M.; Eisen, M. S. Angew. Chem. Int. Ed. Engl. 2015, 54, 12422–12425. DOI: https://doi.org/10.1002/anie.201502041.
   PubMed Web of Science ®Google Scholar
• (a) Bigi, F.; Maggi, R.; Sartori, G. Green Chem. 2000, 2, 140–148. DOI: https://doi.org/10.1039/b002127j.
   Web of Science ®Google Scholar
  (b) Janda, K. D.; Clapham, B.; Lee, S. H.; Matsushita, H. Tetrahedron. 2004, 60, 3439.
   Web of Science ®Google Scholar
  (c) Padiya, K. J.; Gavade, S.; Kardile, B.; Tiwari, M.; Bajare, S.; Mane, M.; Gaware, V.; Varghese, S.; Harel, D.; Kurhade, S. Org. Lett. 2012, 14, 2814–2817. DOI: https://doi.org/10.1021/ol301009d.
   PubMed Web of Science ®Google Scholar
  (d) Xiong, J.; Zhou, S. G.; Yao, T.; Yi, J. C.; Li, D. S. J. Chem. Res. 2013, 37, 315–319. DOI: https://doi.org/10.3184/174751913X13663925002708.
   Google Scholar
• (a) Kaeobamrung, J.; Lanui, A.; Mahawong, S.; Duangmak, W.; Rukachaisirikul, V. RSC Adv. 2015, 5, 58587–58594. DOI: https://doi.org/10.1039/C5RA10060G.
   Web of Science ®Google Scholar
  (b) Reddy, K. R.; Reddy, N. V.; Kumar, P. S.; Reddy, P. S.; Kantam, M. L. New J. Chem. 2015, 39, 805–809. DOI: https://doi.org/10.1039/C4NJ01668H.
   Web of Science ®Google Scholar
  (c) Thakur, G. A.; Kulkarni, A. R.; Garai, S. J. Org. Chem. 2017, 82, 992–999. DOI: https://doi.org/10.1021/acs.joc.6b02521.
   PubMed Web of Science ®Google Scholar
  (d) Zhang, C. P.; Song, H. X.; Han, Z. Z. Chemistry. 2019, 25, 10907–10912. DOI: https://doi.org/10.1002/chem.201901865.
   PubMed Web of Science ®Google Scholar
  (e) Yang, S. K.; Yang, X. J.; Zhao, Y. X.; Xie, T. Eur. J. Org. Chem. 2020, 2020, 437–445. DOI: https://doi.org/10.1002/ejoc.201901602.
   Web of Science ®Google Scholar
  (f) Dubé, P.; Nathel, N. F. F.; Vetelino, M.; Couturier, M.; Aboussafy, C. L.; Pichette, S.; Jorgensen, M. L.; Hardink, M. Org. Lett. 2009, 11, 5622–5625. DOI: https://doi.org/10.1021/ol9023387.
   PubMed Web of Science ®Google Scholar
• (a) Giannoccaro, P.; Nobile, C. F.; Mastrorilli, P.; Ravasio, N. J. Organomet. Chem. 1991, 419, 251–258. DOI: https://doi.org/10.1016/0022-328X(91)86180-X.
   Web of Science ®Google Scholar
  (b) Shi, F.; Deng, Y. Q. J. Catal. 2002, 211, 548–551. DOI: https://doi.org/10.1006/jcat.2002.3772.
   Web of Science ®Google Scholar
  (c) Park, J. H.; Yoon, J. C.; Chung, Y. K. Adv. Synth. Catal. 2009, 351, 1233–1237. DOI: https://doi.org/10.1002/adsc.200900106.
   Web of Science ®Google Scholar
  (d) Zhang, L.; Darko, A. K.; Johns, J. I.; White, L. M. Eur. J. Org. Chem. 2011, 2011, 6261–6268. DOI: https://doi.org/10.1002/ejoc.201100657.
   Web of Science ®Google Scholar
  (e) Guan, Z.-H.; Lei, H.; Chen, M.; Ren, Z.-H.; Bai, Y.; Wang, Y.-Y. Adv. Synth. Catal. 2012, 354, 489–496. DOI: https://doi.org/10.1002/adsc.201100545.
   Web of Science ®Google Scholar
  (f) Liu, S.; Wang, H.; Dai, X.; Shi, F. Green Chem. 2018, 20, 3457–3462. DOI: https://doi.org/10.1039/C8GC00740C.
   Web of Science ®Google Scholar
  (g) Zhang, Z. H.; Zhao, J.; Li, Z. Y.; Yan, S. H.; Xu, S. Y.; Wang, M. A.; Fu, B. Org. Lett. 2016, 18, 1736–1739. DOI: https://doi.org/10.1021/acs.orglett.6b00381.
   PubMed Web of Science ®Google Scholar
  (h) Kim, H.-K.; Lee, A. Org. Biomol. Chem. 2016, 14, 7345–7353. DOI: https://doi.org/10.1039/c6ob01290f.
   PubMed Web of Science ®Google Scholar
  (i) Kang, S.; Kim, H.-K. Tetrahedron. 2018, 74, 4036–4046. DOI: https://doi.org/10.1016/j.tet.2018.06.011.
   Web of Science ®Google Scholar
  (j) Tran, V. H.; Kim, H.-K. New J. Chem. 2019, 43, 14093–14101. DOI: https://doi.org/10.1039/C9NJ03111A.
   Web of Science ®Google Scholar
  (k) Bui, T. T.; Kim, H.-K. Synlett. 2020, 31, 997–1002. DOI: https://doi.org/10.1055/s-0040-1707991.
   Web of Science ®Google Scholar
• (a) Zoeckler, M. T.; Laine, R. M. J. Org. Chem. 1983, 48, 2539–2543. DOI: https://doi.org/10.1021/jo00163a023.
   Web of Science ®Google Scholar
  (b) Shi, F.; Deng, Y.; SiMa, T.; Peng, J.; Gu, Y.; Qiao, B. Angew. Chem. Int. Ed. Engl. 2003, 42, 3257–3260. DOI: https://doi.org/10.1002/anie.200351098.
   PubMed Web of Science ®Google Scholar
  (c) Shi, F.; Zhang, Q.; Ma, Y.; He, Y.; Deng, Y. J. Am. Chem. Soc. 2005, 127, 4182–4183. DOI: https://doi.org/10.1021/ja042207o.
   PubMed Web of Science ®Google Scholar
  (d) Ion, A.; Parvulescu, V.; Jacobs, P.; Vos, D. D. Green Chem. 2007, 9, 158–161. DOI: https://doi.org/10.1039/B612403H.
   Web of Science ®Google Scholar
  (e) Tamura, M.; Ito, K.; Nakagawa, Y.; Tomishige, K. J. Catal. 2016, 343, 75–85. DOI: https://doi.org/10.1016/j.jcat.2015.11.015.
   Web of Science ®Google Scholar
  (f) Stephan, D. W.; Xu, M.; Jupp, A. R. Angew. Chem. Int. Ed. Engl. 2017, 56, 14277–14281. DOI: https://doi.org/10.1002/anie.201708921.
   PubMed Web of Science ®Google Scholar
• (a) Sauer, J.; Mayer, K. K. Tetrahedron Lett. 1968, 9, 319–324. DOI: https://doi.org/10.1016/S0040-4039(01)98753-2.
   Google Scholar
  (b) Eibler, E.; Sauer, J. Tetrahedron Lett. 1974, 15, 2565–2568. DOI: https://doi.org/10.1016/S0040-4039(01)92294-4.
   Google Scholar
  (c) Eibler, E.; Käsbauer, J.; Pohl, H.; Sauer, J. Tetrahedron Lett. 1987, 28, 1097–1100. DOI: https://doi.org/10.1016/S0040-4039(00)95920-3.
   Web of Science ®Google Scholar
• (a) Bogolubsky, A. V.; Ryabukhin, S. V.; Pipko, S. E.; Lukin, O.; Shivanyuk, A.; Mykytenko, D.; Tolmachev, A. Tetrahedron. 2011, 67, 3619–3623. DOI: https://doi.org/10.1016/j.tet.2011.03.101.
   Web of Science ®Google Scholar
  (b) Soto, M.; Sebastián, R. M.; Marquet, J. J. Org. Chem. 2014, 79, 5019–5027. DOI: https://doi.org/10.1021/jo5005789.
   PubMed Web of Science ®Google Scholar
• Schneider, P.; Goodrow, M. H.; Gee, S. J.; Hammock, B. D. J. Agric. Food Chem. 1994, 42, 413–422. DOI: https://doi.org/10.1021/jf00038a033.
   Web of Science ®Google Scholar
• Yin, X. L.; Jiang, L.; Song, N. H.; Yang, H. J. Agric. Food Chem. 2008, 56, 4825–4831. DOI: https://doi.org/10.1021/jf800795v.
   PubMed Web of Science ®Google Scholar
• (a) Kim, J. G.; Park, Y.; Park, K. T.; Chang, S. J. Am. Chem. Soc. 2015, 137, 4534.
   PubMed Web of Science ®Google Scholar
  (b) Bizet, V.; Buglioni, L.; Bolm, C. Angew. Chem. Int. Ed. Engl. 2014, 53, 5639–5642. DOI: https://doi.org/10.1002/anie.201310790.
   PubMed Web of Science ®Google Scholar
  (c) Chen, M.; Sun, N.; Chen, H.; Liu, Y. Chem. Commun. 2016, 52, 6324–6327. DOI: https://doi.org/10.1039/c6cc02776h.
   PubMed Web of Science ®Google Scholar
  (d) Bizet, V.; Bolm, C. Eur. J. Org. Chem. 2015, 2015, 2854–2860. DOI: https://doi.org/10.1002/ejoc.201500220.
   Web of Science ®Google Scholar