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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 53, 2023 - Issue 7-8
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Articles

Metal nitrate promoted highly regiospecific ortho–nitration of phenols: Application to the synthesis of nitroxynil

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Pages 557-567 | Received 19 Jan 2023, Published online: 13 Mar 2023

References

  • Ono, N. The Nitro Group in Organic Synthesis; Wiley-VCH: New York, 2001. DOI: 10.1002/0471224480.
  • Parry, R.; Nishino, S.; Spain, J. Nat. Prod. Rep. 2011, 28, 152–167. DOI: 10.1039/C0NP00024H.
  • (a) Ezaki, N.; Koyama, M.; Shomura, T.; Tsuruoka, T.; Inouye, S. J. Antibiot. 1983, 36, 1263–1267. DOI: 10.7164/antibiotics.36.1483.
  • Hermosilla, L.; Rezende, M. C.; Machado, V. G.; Stock, R. I. Spectrochim. Acta A Mol. Biomol. Spectrosc. 2017, 173, 556–561. DOI: 10.1016/j.saa.2016.10.017.
  • (a) Fletcher, H. J.; Hamilton, C. J.; Hechenbleikner, I.; Hoegberg, I. E.; Sertl, J. B.; Cassaday, T. J. J. Am. Chem. Soc. 1950, 72, 2461. DOI: 10.1021/ja01162a028. (b) Ware, W. G. The Pesticide Book, 4th ed.; Thompson Publications: Fresno, CA, 1994.
  • (a) Lee, P. Explosive Effects and Applications; Springer: Berlin, Germany, 2002. (b) Oxley, C. J. Explosive Effects and Applications; Springer: Berlin, Germany, 2002. (c) Schwarzenbach, P. R.; Gschwend, M. P.; Imboden, M. D. Environmental Organic Chemistry; Wiley-VCH: New York, 2002.
  • Botvay, A.; Mathe, A.; Poppl, L. Polymer 1999, 40, 4965–4970. DOI: 10.1016/S0032-3861(98)00841-6.
  • (a) Feuer, H.; Nielsen, T. A. Nitro Compounds – Recent Advances in Synthesis and Chemistry; VCH, Weinheim, 1990. DOI: 10.1002/adma.19910030316. (b) Ono, N. The Nitro Group in Organic Synthesis; Wiley-VCH, New York, 2001. DOI: 10.1002/0471224480. (c) Ju, S. K.; Parales, E. R. Microbiol. Mol. Biol. Rev. 2010, 74, 250–272. DOI: 10.1128/MMBR.00006-10.
  • Fetscher, A. C. Org. Synth. 1953, 33, 65. DOI: 10.15227/orgsyn.033.0065.
  • Sparks, K. A. J. Org. Chem. 1966, 31, 2299. DOI: 10.1021/jo01345a051.
  • Coon, L. C.; Blucher, G. W.; Hill, E. M. J. Org. Chem. 1973, 38, 4243–4248. DOI: 10.1021/jo00964a007.
  • Wei, T. W.; Zhu, M. W.; Liang, W.; Wu, Y.; Huang, Y. H.; Huang, L. Y.; Luo, J.; Liang, H. Synlett 2017, 28, 2153–2156. DOI: 10.1055/s-0036-1589038.
  • Crivello, V. J. J. Org. Chem. 1981, 46, 3056–3060. DOI: 10.1021/jo00328a013.
  • Verma, S.; Pandita, S.; Jain, L. S. Tetrahedron Lett. 2014, 55, 1320. DOI: 10.1016/j.tetlet.2013.12.114.
  • Li, P. W.; G.; Cheng, Li, Y. S.; Lin, C-Z; Guan, Y. X., Bing X. D., Cao, J., Zhu, D., Deng, H. Q. J. Org. Chem. 2022, 87, 3834–3840. DOI: 10.1021/acs.joc.1c03020.
  • Kumar, S. M.; Sriram, H. Y.; Venkateswarlu, M.; Rajanna, C. K.; Sudhakar, S. M.; Venkanna, P.; Saiprakash, K. P. Synth. Commun. 2018, 48, 59–67. DOI: 10.1080/00397911.2017.1387923.
  • (a) Heravi, M. M.; Oskooie, A. H.; Baghernejad, B. J. Chin. Chem. Soc. 2007, 54, 767–770. DOI: 10.1002/jccs.200700110. (b) Zarchi, K. A. M.; Rahmani, F. J. Appl. Polym. Sci. 2011, 120, 2830–2834. DOI: 10.1002/app.33274.
  • Zhang, W.; Zhang, J.; Ren, S.; Liu, Y. J. Org. Chem. 2014, 79, 11508–11516. DOI: 10.1021/jo502145v.
  • Wasinska, M.; Korczewska, A.; Giurg, M.; Skarzewski, J. Synth. Commun. 2015, 45, 143–150. DOI: 10.1080/00397911.2014.954730.
  • Sun, B. H.; Hua, R.; Yin, Y. J. Org. Chem. 2005, 70, 9071–9073. DOI: 10.1021/jo0514669.
  • Sathunuru, R.; Rao, N. U.; Biehl, E. ARKIVOC 2003, 15, 124–133. DOI: 10.3998/ark.5550190.0004.f14.
  • Anuradha, V.; Srinivas, V. P.; Aparna, P.; Rao, M. J. Tetrahedron Lett. 2006, 47, 4933–4935. DOI: 10.1016/j.tetlet.2006.05.017.
  • Ornelas, J. A. K.; Jimenez, H. O. J.; Kato, T.; Alvarado, S. R. C.; Maruoka, K. Org. Lett. 2019, 21, 1315–1319. DOI: 10.1021/acs.orglett.8b04141.
  • Poirier, M. J.; Vottero, C. Tetrahedron 1989, 45, 1415–1422. DOI: 10.1016/0040-4020(89)80139-5.
  • Firouzabadi, H.; Iranpoor, N.; Zolfigol, A. M. Synth. Commun. 1997, 27, 3301–3311. DOI: 10.1080/00397919708005630.
  • Bigdeli, A. M.; Heravi, M. M.; Nemati, F. Synth. Commun. 2007, 37, 2225–2230. DOI: 10.1080/00397910701397011.
  • Nemati, F.; Kiani, Y. H.; Hyeniaz, S. Synth. Commun. 2011, 41, 2985–2992. DOI: 10.1080/00397911.2010.516054.
  • Vekariya, R. H.; Patel, H. D. Synth. Commun. 2014, 44, 2313–2335. DOI: 10.1080/00397911.2014.896925.
  • Iqbal, Z.; Joshi, A.; De, S. R. Eur. J. Org. Chem. 2022, 31, e202200746. DOI: 10.1002/ejoc.202200746.
  • Larsen, A. A.; Moore, C.; Sprague, J.; Cloke, B.; Moss, J.; Hoppe, O. J. J. Am. Chem. Soc. 1956, 78, 3210–3216. DOI: 10.1021/ja01594a066.
  • Natarajan P.; Chaudhary, R.; Rani N.; Sakshi  ; Venugopalan, P. Tetrahedron Lett. 2020, 61, 151529. DOI: 10.1016/j.tetlet.2019.151529.

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