Recent Advances in Lossen Rearrangement

doi:10.6023/cjoc202202030

Abstract

Isocyanate is an important intermediate in organic synthesis, which could be prepared via the reaction of Hoffman rearrangement, Curtis rearrangement or Lossen rearrangement. Considering avoiding the hazardous and potentially explosive reagents, chemists have focused on Lossen rearrangement and made the progress and applications of this reaction. The development and applications of the typical reactions of Lossen rearrangement based on its mechanism are systematically summarized. The direction of future research is also prospected.

Key words: Lossen rearrangement, hydroxamic acid, isocyanate, synthesis

Cite this article

Yin Cui, Guofu Zhang, Chengrong Ding. Recent Advances in Lossen Rearrangement[J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 2015-2027.

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Fig. & Tab. 35

Scheme 1. Synthesis of isocyanate via rearrangement

Scheme 2. Origin of Lossen rearrangement

Scheme 3. Substrates of classical Lossen rearrangement

Scheme 4. Reaction mechanism of classical Lossen rearrangement

Scheme 5. First report of the “direct Lossen rearrangement”

Scheme 6. Plausible mechanism of Zinc-assisted Lossen rearrangement

Scheme 7. General mechanism of metal-assisted Lossen rearrangement

Scheme 8. Conversion of benzohydroxamic acid to aniline under copper-catalyzed N-arylation conditions

Scheme 9. Self-propagative mechanism for Lossen rearrangement

Scheme 10. Acetic anhydride catalyzed self-propagative Lossen rearrangement

Scheme 11. Acetonitrile catalyzed self-propagative Lossen rearrangement

Scheme 12. CDI-promoted Lossen rearrangement

Scheme 13. TCT-promoted Lossen rearrangement

Scheme 14. BDMS-promoted Lossen rearrangement

Scheme 15. DMC-promoted Lossen rearrangement

Scheme 16. 4-NsCl-promoted Lossen rearrangement

Scheme 17. 4-NBsOXY-promoted Lossen rearrangement

Scheme 18. Boc-Oxyma-promoted Lossen rearrangement

Scheme 19. Plausible mechanism of 4-NBsOXY-promoted Lossen rearrangement

Scheme 20. Plausible mechanism of Boc-Oxyma-promoted Lossen rearrangement

Scheme 21. SO2F2-promoted Lossen rearrangement

Scheme 22. Lossen rearrangement of phosphonic acid derivatives

Scheme 23. Lossen rearrangement of sulfonic acid derivatives

Scheme 24. Fluorogenic and chromogenic reaction of rhodamine-hydroxamate with DCP

Scheme 25. Fluorogenic and chromogenic reaction of PTS with DCP

Scheme 26. Hydrolysis of carcinogenic halogenated quinones via Lossen rearrangement

Scheme 27. Synthesis of phenols via Lossen rearrangement

Scheme 28. Synthesis of amides via Lossen rearrangement

Scheme 29. Synthesis of hydrazine derivatives via Lossen rearrangement

Scheme 30. Combination of Lossen rearrangement and Heck reaction

Scheme 31. Improving oxidative C—H olefination reactions by using internal oxidants

Scheme 32. Synthesis of indole and pyrrole compounds via Lossen rearrangement and C—H bond activation

Scheme 33. Synthesis of spirooxindole pyrrolones via Lossen rearrangement and C—H bond activation

Scheme 34. Rh(III)-Catalyzed C—H activation/selective lactone ring-opening

Scheme 35. C—H activation of aryl hydroxamates with acetylene to quinolone-containing amino acid derivatives via the Lossen rearrangement

References 102

[1]	Guan, A.; Liu, C.; Yang, X.; Dekeyser, M. Chem. Rev. 2014, 114, 7079. doi: 10.1021/cr4005605
[2]	Lambert, W. T.; Buysse, A. M.; Wessels, F. J. Pest Manage. Sci. 2020, 76, 497. doi: 10.1002/ps.5537
[3]	Kozikowski, A. P.; Zhang, J.; Nan, F.; Petukhov, P. A.; Grajkowska, E.; Wroblewski, J. T.; Yamamoto, T.; Bzdega, T.; Wroblewska, B.; Neale, J. H. J. Med. Chem. 2004, 47, 1729. pmid: 15027864
[4]	Frezza, M.; Castang, S.; Estephane, J.; SoulHre, L.; Deshayes, C.; Chantegrel, B.; Nasser, W.; Queneau, Y.; Reverchon, S.; Doutheau, A. Bioorg. Med. Chem. 2006, 14, 4781. doi: 10.1016/j.bmc.2006.03.017
[5]	McGeary, R. P.; Bennett, A. J.; Tran, Q. B.; Cosgrove, K. L.; Ross, B. P. Mini-Rev. Med. Chem. 2008, 8, 1384. pmid: 18991754
[6]	Patrick, D. A.; Gillespie, J. R.; McQueen, J.; Hulverson, M. A.; Ranade, R. M.; Creason, S. A.; Herbst, Z. M.; Gelb, M. H.; Buckner, F. S.; Tidwell, R. R. J. Med. Chem. 2017, 60, 957. doi: 10.1021/acs.jmedchem.6b01163 pmid: 27992217
[7]	López, J. L.; Pérez, E. M.; Viruela, P. M.; Viruela, R.; Ortí, E.; Martín, N. Org. Lett. 2009, 11, 4524. doi: 10.1021/ol901695m pmid: 19754141
[8]	Dawn, S.; Dewal, M. B.; Sobransingh, D.; Paderes, M. C.; Wibowo, A. C.; Smith, M. D.; Krause, J. A.; Pellechia, P. J. J. Am. Chem. Soc. 2011, 133, 7025. doi: 10.1021/ja110779h
[9]	Tsopmo, A.; Ngnokam, D.; Ngamga, D.; Ayafor, J. F.; Sterner, O. J. Nat. Prod. 1999, 62, 1435. pmid: 10543911
[10]	Kimmel, K. L.; Robak, M. T.; Ellman, J. A. J. Am. Chem. Soc. 2009, 131, 8754. doi: 10.1021/ja903351a pmid: 19496569
[11]	Zhu, B.; Lee, R.; Li, J.; Ye, X.; Hong, S.-N.; Qiu, S.; Coote, M. L.; Jiang, Z. Angew. Chem., Int. Ed. 2016, 55, 1299. doi: 10.1002/anie.201507796
[12]	Sun, L.; Wu, X.; Xiong, D.; Ye, X. Angew. Chem., Int. Ed. 2016, 55, 8041. doi: 10.1002/anie.201600142
[13]	Bar, G. L. J.; Lloyd-Jones, G. C.; Booker-Milburn, K. I. J. Am. Chem. Soc. 2005, 127, 7308. doi: 10.1021/ja051181d
[14]	Clayden, J.; Dufour, J.; Grainger, D. M.; Helliwell, M. J. Am. Chem. Soc. 2007, 129, 7488. doi: 10.1021/ja071523a
[15]	Twitchett, H. J. Chem. Soc. Rev. 1974, 3, 209.
[16]	Paul, F. Coord. Chem. Rev. 2000, 203, 269. doi: 10.1016/S0010-8545(99)00230-1
[17]	Uriz, P.; Serra, M.; Salagre, P.; Castillon, S.; Claver, C.; Fernandez, E. Tetrahedron Lett. 2002, 43, 1673. doi: 10.1016/S0040-4039(02)00094-1
[18]	Curtius, T. J. Prakt. Chem. 1894, 50, 275. doi: 10.1002/prac.18940500125
[19]	Scriven, E. F. V.; Turnbull, K. Chem. Rev. 1988, 88, 297. doi: 10.1021/cr00084a001
[20]	Wolff, M. E. Chem. Rev. 1963, 63, 55. doi: 10.1021/cr60221a004
[21]	Yale, H. L. Chem. Rev. 1943, 33, 209. doi: 10.1021/cr60106a002
[22]	Lossen, W. Z. Chem. 1865, 8, 551.
[23]	Lossen, H. Liebigs Ann. Chem. 1869, 150, 314. doi: 10.1002/jlac.18691500304
[24]	Lossen, W. Liebigs Ann. Chem. 1872, 150, 314. doi: 10.1002/jlac.18691500304
[25]	Lossen, W. Liebigs Ann. Chem. 1877, 186, 1. doi: 10.1002/jlac.18771860102
[26]	Lossen, W. Liebigs Ann. Chem. 1889, 252, 170. doi: 10.1002/jlac.18892520112
[27]	Lossen, W. Liebigs Ann. Chem. 1894, 281, 169. doi: 10.1002/jlac.18942810202
[28]	Bright, R. D.; Hauser, C. R. J. Am. Chem. Soc. 1939, 61, 618. doi: 10.1021/ja01872a022
[29]	Swenson, J. S.; Davis, A. M.; Deyo, R. A.; Graham, B. W.; Jahn, E. P.; Mattice, J. D. J. Org. Chem. 1973, 38, 3956. doi: 10.1021/jo00962a034
[30]	Tiemann, F. Ber. Dtsch. Chem. Ges. Beil. 1891, 24, 4162.
[31]	Exner, O. Collect. Czech. Chem. Commun. 1962, 27, 2284. doi: 10.1135/cccc19622284
[32]	Bauer, L.; Miarka, S. V. J. Org. Chem. 1959, 24, 1293. doi: 10.1021/jo01091a035
[33]	Podlaha, J.; Císařová, I.; Soukupová, L.; Schraml, J.; Exner, O. J. Chem. Res., Synop. 1998, 520.
[34]	Ducháčková, L.; Roithová, J. Chem.-Eur. J. 2009, 15, 13399. doi: 10.1002/chem.200901645
[35]	Jašíková, L.; Hanikýřová, E.; Škríba, A.; Jašík, J.; Roithová, J. J. Org. Chem. 2012, 77, 2829. doi: 10.1021/jo300031f pmid: 22360436
[36]	Hoshino, Y.; Okuno, M.; Kawamura, E.; Honda, K.; Inoue, S. Chem. Commun. 2009, 2281.
[37]	Ohtsuka, N.; Okuno, M.; Hoshino, Y.; Honda, K. Org. Biomol. Chem. 2016, 14, 9046. doi: 10.1039/c6ob01178k pmid: 27605448
[38]	Hoshino, Y.; Shimbo, Y.; Ohtsuka, N.; Honda, K. Tetrahedron Lett. 2015, 56, 710. doi: 10.1016/j.tetlet.2014.12.084
[39]	Strotman, N. A.; Ortiz, A.; Savage, S. A.; Wilbert, C. R.; Ayers, S.; Kiau, S. J. Org. Chem. 2017, 82, 4044. doi: 10.1021/acs.joc.7b00450 pmid: 28394130
[40]	Ortiz, A.; Soumeillant, M.; Savage, S. A.; Strotman, N. A.; Haley, M.; Benkovics, T.; Nye, J.; Xu, Z.; Tan, Y.; Ayers, S.; Gao, Q.; Kiau, S. J. Org. Chem. 2017, 82, 4958. doi: 10.1021/acs.joc.7b00438
[41]	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. doi: 10.1021/ol9023387
[42]	Hamon, F.; Prié, G.; Lecornué, F.; Papot, S. Tetrahedron Lett. 2009, 50, 6800. doi: 10.1016/j.tetlet.2009.09.115
[43]	Yadav, D. K.; Yadav, A. K.; Srivastava, V. P.; Watal, G.; Yadav, L. D. S. Tetrahedron Lett. 2012, 53, 2890. doi: 10.1016/j.tetlet.2012.03.129
[44]	Fiorani, G.; Perosa, A.; Selva, M. Green Chem. 2018, 20, 288. doi: 10.1039/C7GC02118F
[45]	Mutlu, H.; Ruiz, J.; Solleder, S. C.; Meier, M. A. Green Chem. 2012, 14, 1728. doi: 10.1039/c2gc35191a
[46]	Kreye, O.; Wald, S.; Meier, M. A. R. Adv. Synth. Catal. 2013, 355, 81. doi: 10.1002/adsc.201200760
[47]	Yoganathan, S.; Miller, S. J. Org. Lett. 2013, 15, 602. doi: 10.1021/ol303424b pmid: 23327543
[48]	Thalluri, K.; Manne, S. R.; Dev, D.; Mandal, B. J. Org. Chem. 2014, 79, 3765. doi: 10.1021/jo4026429 pmid: 24678821
[49]	Manne, S. R.; Thalluri, K.; Giri, S. R.; Chandra, J.; Mandal, B. Adv. Synth. Catal. 2017, 359, 168. doi: 10.1002/adsc.201600661
[50]	Dong, J.; Krasnova, L.; Finn, M. G.; Sharpless, K. B. Angew. Chem.,Int. Ed. 2014, 53, 9430. doi: 10.1002/anie.201309399
[51]	Chen, W.; Dong, J.; Plate, L.; Mortenson, D. E.; Brighty, G. J.; Li, S.; Liu, Y.; Galmozzi, A.; Lee, P. S.; Hulce, J. J.; Cravatt, B. F.; Saez, E.; Powers, E. T.; Wilson, I. A.; Sharpless, K. B.; Kelly, J. W. J. Am. Chem. Soc. 2016, 138, 7353. doi: 10.1021/jacs.6b02960
[52]	Gao, B.; Zhang, L.; Zheng, Q.; Zhou, F.; Klivansky, L. M.; Lu, J.; Liu, Y.; Dong, J.; Wu, P.; Sharpless, K. B. Nat. Chem. 2017, 9, 1083. doi: 10.1038/nchem.2796
[53]	Zhao, Q.; Ouyang, X.; Wan, X.; Gajiwala, K. S.; Kath, J. C.; Jones, L. H. A.; Burlingame, L.; Taunton, J. J. Am. Chem. Soc. 2017, 139, 680. doi: 10.1021/jacs.6b08536
[54]	Liu, Z.; Li, J.; Li, S.; Li, G.; Sharpless, K. B.; Wu, P. J. Am. Chem. Soc. 2018, 140, 2919. doi: 10.1021/jacs.7b12788
[55]	Mortenson, D. E.; Brighty, G. J.; Plate, L.; Bare, G.; Chen, W.; Li, S.; Wang, H.; Cravatt, B. F.; Forli, S.; Powers, E. T.; Sharpless, K. B.; Wilson, I. A.; Kelly, J. W. J. Am. Chem. Soc. 2018, 140, 200. doi: 10.1021/jacs.7b08366 pmid: 29265822
[56]	Wang, N.; Yang, B.; Fu, C.; Zhu, H.; Zheng, F.; Kobayashi, T.; Liu, J.; Li, S.; Ma, C.; Wang, P. G.; Wang, Q.; Wang, L. J. Am. Chem. Soc. 2018, 140, 4995. doi: 10.1021/jacs.8b01087
[57]	Hanley, P. S.; Clark, T. P.; Krasovskiy, A. L.; Ober, M. S.; O'Brien, J. P.; Staton, T. S. ACS Catal. 2016, 6, 3515. doi: 10.1021/acscatal.6b00865
[58]	Schimler, S. D.; Cismesia, M. A.; Hanley, P. S.; Froese, R. D. J.; Jansma, M. J.; Bland, D. C.; Sanford, M. S. J. Am. Chem. Soc. 2017, 139, 1452. doi: 10.1021/jacs.6b12911 pmid: 28111944
[59]	Epifanov, M.; Foth, P. J.; Gu, F.; Barrillon, C.; Kanani, S. S.; Higman, C. S.; Hein, J. E.; Sammis, G. M. J. Am. Chem. Soc. 2018, 140, 16464. doi: 10.1021/jacs.8b11309 pmid: 30433772
[60]	Zha, G. F.; Fang, W. Y.; Li, Y. G.; Leng, J.; Chen, X.; Qin, H. L. J. Am. Chem. Soc. 2018, 140, 17666. doi: 10.1021/jacs.8b10069
[61]	Zhao, C.; Fang, W. Y.; Rakesh, K. P.; Qin, H. L. Org. Chem. Front. 2018, 5, 1 835. doi: 10.1039/C8QO00295A
[62]	Fang, W. Y.; Zha, G. F.; Qin, H. L. Org. Lett. 2019, 21, 8657. doi: 10.1021/acs.orglett.9b03274
[63]	Jiang, Y.; Sun, B.; Fang, W. Y.; Qin, H. L. Eur. J. Org. Chem. 2019, 3190.
[64]	Lekkala, R.; Lekkala, R.; Moku, B.; Rakesh, K. P.; Qin, H. L. Org. Chem. Front. 2019, 6, 3490. doi: 10.1039/C9QO00747D
[65]	Fang, W. Y.; Zha, G. F.; Zhao, C.; Qin, H. L. Chem. Commun. 2019, 55, 6273. doi: 10.1039/C9CC02659B
[66]	Leng, J.; Qin, H. L. Org. Biomol. Chem. 2019, 17, 5001. doi: 10.1039/C9OB00903E
[67]	Zha, G. F.; Fang, W. Y.; Leng, J.; Qin, H. L. Adv. Synth. Catal. 2019, 361, 2262. doi: 10.1002/adsc.201900104
[68]	Zhang, X.; Rakesh, K. P.; Qin, H. L. Chem. Commun. 2019, 55, 2845. doi: 10.1039/C8CC09693G
[69]	Lekkala, R.; Mokua, B.; Qin, H. L. Org. Chem. Front. 2019, 6, 796. doi: 10.1039/C8QO01388H
[70]	Zhao, Y.; Zhang, G.; Ding, C. Synlett 2019, 30, 1484. doi: 10.1055/s-0037-1611840
[71]	Zhang, G.; Zhao, Y.; Xuan, L.; Ding, C. Eur. J. Org. Chem. 2019, 4911.
[72]	Zhao, Y.; Zhang, G.; Ding, C. Org. Biomol. Chem. 2019, 17, 7684. doi: 10.1039/C9OB01547G
[73]	Zhang, G.; Cui, Y.; Zhao, Y.; Cui, Y.; Bao, S.; Ding, C. ChemistrySelect 2020, 5, 7817 doi: 10.1002/slct.202002270
[74]	Harger, M. J. P. J. Chem. Soc., Perkin Trans. 2 1999, 159.
[75]	Martin, J. P. J. Chem. Soc., Chem. Commun. 1994, 1619.
[76]	Pantaine, L.; Richard, F.; Marrot, J.; Moreau, X.; Coeffard, V.; Greck, C. Adv. Synth. Catal. 2016, 358, 2012. doi: 10.1002/adsc.201501139
[77]	Han, S.; Xue, Z.; Wang, Z.; Wen, T. B. Chem. Commun. 2010, 46, 8413. doi: 10.1039/c0cc02881a
[78]	Lei, Z.; Yang, Y. J. Am. Chem. Soc. 2014, 136, 6594. doi: 10.1021/ja502945q
[79]	Huo, B.; Du, M.; Shen, A.; Li, M.; Lai, Y.; Gong, A.; Bai, X. Anal. Chem. 2019, 91, 10979. doi: 10.1021/acs.analchem.9b01006
[80]	Codd, R. Coord. Chem. Rev. 2008, 252, 1387. doi: 10.1016/j.ccr.2007.08.001
[81]	Monneret, C. Eur. J. Org. Chem. 2005, 40, 1.
[82]	Thomas, M.; Rivault, F.; Tranoy-Opalinski, I.; Roche, J.; Gesson, J. P.. Papot2, S. Bioorg. Med. Chem. Lett. 2007, 17, 983. doi: 10.1016/j.bmcl.2006.11.042
[83]	Shen, S.; Kozikowski, A. P. ChemMedChem 2016, 11, 15. doi: 10.1002/cmdc.201500486
[84]	Richon, V. M.; Emiliani, S.; Verdin, E.; Webb, Y.; Breslow, R.; Rifkind, R. A.; Marks, P. A. Proc. Natl. Acad. Sci. U. S. A. 1998. 95, 3003. pmid: 9501205
[85]	Ganeshpurkar, A.; Kumar, D.; Singh, S K. Curr. Org. Synth. 2018, 15, 154. doi: 10.2174/1570179414666170614123508
[86]	Thomas, M.; Alsarraf, J.; Araji, N.; Tranoy-Opalinski, I.; Renoux, B.; Papot, S. Org. Biomol. Chem. 2019, 17, 5420. doi: 10.1039/C9OB00789J
[87]	Shan, G. Q.; Yu, A.; Zhao, C. F.; Huang, C. H.; Zhu, L. Y.; Zhu, B. Z. J. Org. Chem. 2015, 80, 180. doi: 10.1021/jo5022713
[88]	Zhu, B. Z.; Zhu, J. G.; Mao, L.; Kalyanaraman, B.; Shan, G. Q. Proc. Natl. Acad. Sci. U. S. A. 2010, 107, 20686. doi: 10.1073/pnas.1010950107
[89]	Li, F.; Huang, C. H.; Xie, L. N.; Qu, N.; Shao, J.; Shao, B.; Zhu, B. Z. Sci. Rep. 2016, 6, 1. doi: 10.1038/s41598-016-0001-8
[90]	Fier, P. S.; Maloney, K. M. Org. Lett. 2016, 18, 2244. doi: 10.1021/acs.orglett.6b00876
[91]	Jia, M.; Zhang, H.; Lin, Y.; Chen, D.; Chen, Y.; Xia, Y. Org. Biomol. Chem. 2018, 16, 3615. doi: 10.1039/C8OB00490K
[92]	Polat, D. E.; Brzezinski, D. D.; Beauchemin, A. M. Org. Lett. 2019, 21, 4849. doi: 10.1021/acs.orglett.9b01742
[93]	AbdelHafez, E. S. M.; Aly, O. M.; Abuo-Rahma, G. E. D. A.; King, S. B. Adv. Synth. Catal. 2014, 356, 3456. doi: 10.1002/adsc.201400170
[94]	Guimond, N.; Gouliaras, C.; Fagnou, K. J. Am. Chem. Soc. 2010, 132, 6908. doi: 10.1021/ja102571b
[95]	Wang, D. H.; Wasa, M.; Giri, R.; Yu, J. Q. J. Am. Chem. Soc. 2008, 130, 7190. doi: 10.1021/ja801355s
[96]	Rakshit, S.; Grohmann, C.; Besset, T.; Glorius, F. J. Am. Chem. Soc. 2011, 133, 2350. doi: 10.1021/ja109676d pmid: 21275421
[97]	Guimond, N.; Gorelsky, S. I.; Fagnou, K. J. Am. Chem. Soc. 2011, 133, 6449. doi: 10.1021/ja201143v
[98]	Yamada, T.; Shibata, Y.; Kawauchi, S.; Yoshizaki, S.; Tanaka, K. Chem.-Eur. J. 2018, 24, 5723.
[99]	Yamada, T.; Shibata, Y.; Tanaka, K. Chem.-Eur. J. 2019, 25, 16022.
[100]	Ma, B.; Wu, P.; Wang, X.; Wang, Z.; Lin, H. X.; Dai, H. X. Angew. Chem., Int. Ed. 2019, 58, 13335. doi: 10.1002/anie.201906589
[101]	Bian, M.; Mawjuda, H.; Gao., H.; Xu, H.; Zhou, Z.; Yi, W. Org. Lett. 2020, 22, 9677. doi: 10.1021/acs.orglett.0c03734
[102]	Petropavlovskikh, D. A.; Vorobyeva, D. V.; Godovikov, I. A.; Nefedov, S. E.; Filippov, O. A.; Osipov, S. N. Org. Biomol. Chem. 2021, 19, 9421. doi: 10.1039/d1ob01711j pmid: 34668894

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