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Synthesis 2022; 54(02): 411-420
DOI: 10.1055/s-0040-1719833
DOI: 10.1055/s-0040-1719833
paper
Intramolecular Chalcogenylation of Isooxazolines Mediated by PhICl2 and Diorganyl Disulfides or Diselenides
Y. Du acknowledges the National Natural Science Foundation of China (#22071175) and F. Sun acknowledges the National Natural Science Foundation of China (U20A20144) for financial supports.
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Abstract
Reactive organosulfenyl chlorides (ArSCl) or selenenyl chlorides (ArSeCl), generated in situ from the reaction of PhICl2 with diorganyl disulfides or diselenides, enable the intramolecular oxidative cyclization/chalcogenylation of β,γ-unsaturated oximes, leading to the formation of a series of chalcogenylated isooxazolines in good to excellent yield.
Key words
chalcogenylation - organosulfenyl chloride (ArSCl) - PhICl2 - organoselenenyl chloride - isooxazolineSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1719833.
- Supporting Information
Publication History
Received: 26 July 2021
Accepted after revision: 24 August 2021
Article published online:
22 September 2021
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References
- 1a Castellano S, Kuck D, Viviano M, Yoo J, López-Vallejo F, Conti P, Tamborini L, Pinto A, Medina-Franco JL, Sbardella G. J. Med. Chem. 2011; 54: 7663
- 1b Kaur K, Kumar V, Sharma AK, Gupta GK. Eur. J. Med. Chem. 2014; 77: 121
- 1c Poutiainen PK, Venäläinen TA, Peräkylä M, Matilainen JM, Väisänen S, Honkakoski P, Laatikainen R, Pulkkinen JT. Bioorg. Med. Chem. 2010; 18: 3437
- 1d Simoni D, Rondanin R, Baruchello R, Rizzi M, Grisolia G, Eleopra M, Grimaudo S, Cristina AD, Pipitone MR, Bongiorno MR, Aricò M, Invidiata FP, Tolomeo M. J. Org. Chem. 2008; 51: 4796
- 2a Zhang W, Su Y, Wang K.-H, Wu L, Chang B, Shi Y, Huang D, Hu Y. Org. Lett. 2017; 19: 376
- 2b Kong W, Guo Q, Xu Z, Wang G, Jiang X, Wang R. Org. Lett. 2015; 17: 3686
- 2c Li W, Jia P, Han B, Li D, Yu W. Tetrahedron 2013; 69: 3274
- 2d Tripathi CB, Mukherjee S. Angew. Chem. Int. Ed. 2013; 52: 8450
- 2e Zhu L, Yu H, Xu Z, Jiang X, Lin L, Wang R. Org. Lett. 2014; 16: 1562
- 2f Zhu M.-K, Zhao J.-F, Loh T.-P. J. Am. Chem. Soc. 2010; 132: 6284
- 2g Yang S, Li H, Li P, Yang J, Wang L. Org. Biomol. Chem. 2020; 18: 715
- 2h Jiang D, Peng J, Chen Y. Org. Lett. 2008; 10: 1695
- 2i Li X.-T, Lv L, Wang T, Gu Q.-S, Xu G.-X, Li Z.-L, Ye L, Zhang X, Cheng G.-J, Liu X.-Y. Chem 2020; 6: 1692
- 2j Zhu L, Wang G, Guo Q, Xu Z, Zhang D, Wang R. Org. Lett. 2014; 16: 5390
- 2k Hu X.-Q, Feng G, Chen J.-R, Yan D.-M, Zhao Q.-Q, Wei Q, Xiao W.-J. Org. Biomol. Chem. 2015; 13: 3457
- 2l Liu R.-H, Wei D, Han B, Yu W. ACS Catal. 2016; 6: 6525
- 2m Li X.-T, Gu Q.-S, Dong X.-Y, Meng X, Liu X.-Y. Angew. Chem. Int. Ed. 2018; 57: 7668
- 2n Yu W, Yang S, Wang P.-L, Li P, Li H. Org. Biomol. Chem. 2020; 18: 7165
- 2o Yu J.-M, Cai C. Org. Biomol. Chem. 2018; 16: 490
- 2p Mallick S, Baidya M, Mahanty K, Maiti D, De Sarkar S. Adv. Synth. Catal. 2020; 362: 1046
- 3a Fotsing JR, Banert K. Eur. J. Org. Chem. 2005; 3704
- 3b Boyarskikh V, Nyong A, Rainier JD. Angew. Chem. Int. Ed. 2008; 47: 5374
- 3c Chen Y, Cho C.-H, Shi F, Larock RC. J. Org. Chem. 2009; 74: 6802
- 3d Lee CH, Kim YH. Tetrahedron Lett. 1991; 32: 2401
- 3e Creary X, Mehrsheikh-Mohammadi ME, Eggers MD. J. Am. Chem. Soc. 1987; 109: 2435
- 3f Vas’kevich AI, Vovk MV. Russ. J. Org. Chem. 2017; 53: 270
- 3g Vas’kevich RI, Dyachenko IV, Vas’kevich AI, Rusanov EB, Vovk MV. Russ. J. Org. Chem. 2015; 51: 556
- 3h Shang J.-L, Guo H, Li Z.-S, Ren B, Li Z.-M, Dai H.-q, Zhang L.-X, Wang J.-G. Bioorg. Med. Chem. Lett. 2013; 23: 724
- 3i Vas’kevich AI, Tsizorik NM, Rusanov EB, Stanitets VI, Vovk MV. Russ. J. Org. Chem. 2011; 47: 1146
- 3j Mori T, Nishimura T, Yamamoto T, Doi I, Miyazaki E, Osaka I, Takimiya K. J. Am. Chem. Soc. 2013; 135: 13900
- 3k Ismailov IE, Ivanov IK, Christov VC. Molecules 2014; 19: 11056
- 3l Bondarenko NA, Vas’kevich AI, Bol’but AV, Rusanov EB, Vovk MV. Russ. J. Org. Chem. 2015; 51: 1774
- 3m Ishii Y, Ito S, Saito Y, Uno D, Oba T. Tetrahedron 2015; 71: 8892
- 3n Danyliuk IY, Vas’kevich RI, Vas’kevich AI, Rusanov EB, Vovk MV. Phosphorus, Sulfur Silicon Relat. Elem. 2019; 194: 156
- 3o Wang D, Zhang R, Lin S, Yan Z, Guo S. Synlett 2016; 27: 2003
- 3p Tuladhar SM, Fallis AG. Tetrahedron Lett. 1987; 28: 523
- 3q Gogoi P, Kalita M, Barman P. Synlett 2014; 25: 866
- 3r Pandey G, Varkhedkar R, Tiwari D. Org. Biomol. Chem. 2015; 13: 4438
- 3s Halle MB, Yudhistira T, Lee W.-H, Mulay SV, Churchill DG. Org. Lett. 2018; 20: 3557
- 3t Huang X, Zhong P, Guo W.-R. Org. Prep. Proced. Int. 1999; 31: 201
- 4a Deng K, Chalker J, Yang A, Cohen T. Org. Lett. 2005; 7: 3637
- 4b Bertran JC, Montforts F.-P. Eur. J. Org. Chem. 2017; 1608
- 4c Feldman KS, Vidulova DB. Org. Lett. 2004; 6: 1869
- 5a Jarboe SG, Terrazas MS, Beak P. J. Org. Chem. 2008; 73: 9627
- 5b Garratt DG, Ryan MD, Kabo A. Can. J. Chem. 1980; 58: 2329
- 5c Reich HJ, Renga JM, Reich IL. J. Am. Chem. Soc. 1975; 97: 5434
- 5d Mueller WH, Butler PE. J. Am. Chem. Soc. 1968; 90: 2075
- 5e Li Z.-S, Wang W.-M, Lu W, Niu C.-W, Li Y.-H, Li Z.-M, Wang J.-G. Bioorg. Med. Chem. Lett. 2013; 23: 3723
- 5f Iwasaki M, Fujii T, Yamamoto A, Nakajima K, Nishihara Y. Chem. Asian J. 2014; 9: 58
- 5g Chen Y, Li M, Gong Z, Shen Z. Phosphorus, Sulfur Silicon Relat. Elem. 2021; 196: 19
- 5h Cheng J.-H, Ramesh C, Kao H.-L, Wang Y.-J, Chan C.-C, Lee C.-F. J. Org. Chem. 2012; 77: 10369
- 5i Yadav JS, Subba Reddy BV, Jain R, Baishya G. Tetrahedron Lett. 2008; 49: 3015
- 5j Schmid GH, Garratt DG. Tetrahedron 1978; 34: 2869
- 5k Li L, Wang X, Li Q, Liu P, Xu K, Chen H, Tang B. Chem. Commun. 2015; 51: 11317
- 5l Makarov AG, Grayfer TD, Makarov AY, Bagryanskaya IY, Vasiliev VG, Zibarev AV. Mendeleev Commun. 2011; 21: 320
- 5m Schlosser KM, Krasutsky AP, Hamilton HW, Reed JE, Sexton K. Org. Lett. 2004; 6: 819
- 5n Kumamoto H, Onuma S, Tanaka H. J. Org. Chem. 2004; 69: 72
- 6 Xing L, Zhang Y, Li B, Du Y. Org. Lett. 2019; 21: 3620
- 7 Shang Z, Chen Q, Xing L, Zhang Y, Wait L, Du Y. Adv. Synth. Catal. 2019; 361: 4926
- 8a Ortgies S, Breder A. ACS Catal. 2017; 7: 5828
- 8b Ai Z, Xiao J, Li Y, Guo B, Du Y, Zhao K. Org. Chem. Front. 2020; 7: 3935
- 8c An R, Liao L, Liu X, Song S, Zhao X. Org. Chem. Front. 2018; 5: 3557
- 9 Zhao X.-F, Zhang C. Synthesis 2007; 551