CC BY-NC-ND 4.0 · SynOpen 2020; 04(04): 99-106
DOI: 10.1055/s-0040-1705982
paper

Iodine-Mediated Facile One-Pot Access to N-Aryl-2-benzoxazolamines

Haruna Nariki
,
Takuya Miyamura
,
Daiki Matsui
,
Motohiro Sonoda
,
This work was supported by Japan Society for the Promotion of Science (JSPS KAKENHI JP 17K07776 to S.T. and JP 17H06092).


Abstract

Facile, iodine-mediated access to N-aryl-2-benzoxazolamines has been achieved in a one-pot manner under mild reaction conditions. Reaction of 2-aminophenols and aryl isothiocyanates afforded N-aryl-2-benzoxazolamines in the presence of molecular iodine and pyridine in tetrahydrofuran at room temperature in moderate to excellent yields.

Supporting Information



Publikationsverlauf

Eingereicht: 12. Oktober 2020

Angenommen nach Revision: 11. November 2020

Publikationsdatum:
24. November 2020 (online)

© 2020. This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial-License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/)

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  • References

  • 1 Wang G, Peng Z, Wang J, Li J, Li X. Bioorg. Med. Chem. 2016; 24: 5374
  • 2 Ramana MM. V, Sharma MR. J. Chem. Pharm. Res. 2013; 5: 122
  • 3 Katari NK, Venkatanarayana M, Srinivas K. J. Chem. Sci. 2015; 127: 447
  • 4 Song H, Oh SR, Lee HK, Han G, Kim JH, Chang HW, Doh KE, Rhee HK, Choo HY. Bioorg. Med. Chem. 2010; 18: 7580
  • 5 Smith ND, Bonnefous C, Zhuang H, Chen X, Duron S, Lindstrom A. PCT Int. Appl (2009) WO 2009029617 A1, 2009
  • 6 Suzuki T, Igari S, Hirasawa A, Hata M, Ishiguro M, Fujieda H, Itoh Y, Hirano T, Nakagawa H, Ogura M, Makishima M, Tsujimoto G, Miyata N. J. Med. Chem. 2008; 51: 7640
  • 7 Murata Y, Matsumoto N, Miyata M, Kitamura Y, Kakusawa N, Matsumura M, Yasuike S. J. Organomet. Chem. 2018; 859: 18
  • 8 Wang G.-c, Wang J, Li L.-y, Chen S, Peng Y.-p, Xie Z.-z, Chen M, Deng B, Li W.-b. Heterocycles 2017; 94: 1257
  • 9 Yadav VK, Srivastava VP, Yadav LD. S. Tetrahedron Lett. 2018; 59: 252
  • 10 Mastalir M, Pittenauer E, Stoeger B, Allmaier G, Kirchner K. Org. Lett. 2017; 19: 2178
  • 11 Phakhodee W, Duangkamol C, Wiriya N, Pattarawarapan M. Tetrahedron Lett. 2016; 57: 5290
  • 12 Daswani U, Dubey N, Sharma P, Kumar A. New J. Chem. 2016; 40: 8093
  • 13 Yadav VK, Srivastava VP, Yadav LD. S. Tetrahedron Lett. 2016; 57: 155
  • 14 Zhang Z, Wang F.-J, Wu H.-H, Tan Y.-J. Chem. Lett. 2015; 44: 440
  • 15 Xu J, Li J, Wei Z, Zhang Q, Shi D. RSC Adv. 2013; 3: 9622
  • 16 Khatik GL, Dube N, Pal A, Nair VA. Synth. Commun. 2011; 41: 2631
  • 17 Zhang X, Jia X, Wang J, Fan X. Green Chem. 2011; 13: 413
  • 18 Yella R, Patel BK. J. Comb. Chem. 2010; 12: 754
  • 19 Ghosh H, Yella R, Nath J, Patel BK. Eur. J. Org. Chem. 2008; 6189
  • 20 Heinelt U, Schultheis D, Jaeger S, Lindenmaier M, Pollex A, Beckmann HS. G. Tetrahedron 2004; 60: 9883
  • 21 Chang HS, Yon GH, Kim YH. Chem. Lett. 1986; 15: 1291
    • 22a Garín J, Meléndez E, Merchán FL, Merino P, Orduna J, Tejero T. J. Heterocycl. Chem. 1991; 28: 359
    • 22b Qian X, Xu X, Li Z, Li Z, Song G. J. Fluorine Chem. 2004; 125: 1609
  • 23 El Gaby MS. A, Micky JA, Taha NM, El Sharief MA. M. Sh. J. Chin. Chem. Soc. 2002; 49: 407
  • 24 Use of molecular iodine for a similar transformation has already been reported by Phakhodee and co-workers.11 However, the reaction requires the addition of triphenylphosphine (1.5 equiv) in dichloromethane under microwave irradiation conditions.