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Synthesis 2014; 46(04): 503-509
DOI: 10.1055/s-0033-1340464
DOI: 10.1055/s-0033-1340464
paper
One-Pot Synthesis of Isoxazolines from Aldehydes Catalyzed by Iodobenzene
Weitere Informationen
Publikationsverlauf
Received: 24. Oktober 2013
Accepted after revision: 25. November 2013
Publikationsdatum:
12. Dezember 2013 (online)
Abstract
A convenient one-pot, three-step procedure for the synthesis of isoxazolines starting from aldehydes has been developed involving catalytic cycloaddition between nitrile oxides and alkenes, in which iodobenzene is used as the catalyst for the in situ generation of a hypervalent iodine intermediate. In this approach, the aldehydes are first transformed with hydroxylamine sulfate into aldoximes, which are then oxidized to nitrile oxides by the in situ generated hypervalent iodine intermediate; finally, a 1,3-dipolar cycloaddition between the nitrile oxides and alkenes occurs to provide the isoxazolines in moderate to good yields.
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References
- 1a Kozikowski AP. Acc. Chem. Res. 1984; 17: 410
- 1b Shankar BB, Yang DY, Girton S, Gangully AK. Tetrahedron Lett. 1998; 39: 2447
- 1c Sammelson RE, Ma T, Galietta LJ. V, Verkman AS, Kurth MJ. Bioorg. Med. Chem. Lett. 2003; 13: 2509
- 1d Bal G, der Venken PV, Antonov D, Lambeir A.-M, Grellier P, Croft SL, Augustyns K, Haemers A. Bioorg. Med. Chem. Lett. 2003; 13: 2875
- 1e Park K.-K, Ko D.-H, You Z, Khan MO. F, Lee HJ. Steroids 2006; 71: 183
- 1f Gopalsamy A, Shi M, Golas J, Vogan E, Jacob J, Johnson M, Lee F, Nilakantan R, Petersen R, Svenson K, Chopra R, Tam MS, Wen Y, Ellingboe J, Arndt K, Boschelli F. J. Med. Chem. 2008; 51: 373
- 1g Lamani RS, Shetty NS, Kamble RR, Khazi IA. M. Eur. J. Med. Chem. 2009; 44: 282
- 1h Pulkkinen JT, Honkakoski P, Peräkylä M, Berczi I, Laatikainen R. J. Med. Chem. 2008; 51: 3562
- 1i Castellano S, Kuck D, Viviano M, Yoo J, Lopez-Vallejo F, Conti P, Tamborini L, Pinto A, Medina-Franco JL, Sbardella G. J. Med. Chem. 2011; 54: 7663
- 2a Huisgen R. 1,3-Dipolar Cycloaddition Chemistry . Vols. 1 and 2. Padwa A. Wiley; New York: 1984
- 2b Torssell KB. G. Nitrile Oxides, Nitrones, and Nitronates in Organic Synthesis. VCH; New York: 1988
- 2c Jaeger V, Colinas PA. Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Towards Heterocycles and Natural Products. Vol. 59. Padwa A. Wiley; Hoboken: 2002: 361
- 2d Grundmann C. Synthesis 1970; 344
- 2e Larsen KE, Torssell KB. G. Tetrahedron 1984; 40: 2985
- 3a Amstrong SK, Collington EW, Knight JG, Naylor A, Warren S. J. Chem. Soc., Perkin Trans. 1 1993; 1433
- 3b Katritzky AR, Button MA. C, Denisenko SN. J. Heterocycl. Chem. 2000; 37: 1505
- 3c Lee GA. Synthesis 1982; 508
- 3d Gi H.-J, Xiang Y, Schinazi RF, Zhao K. J. Org. Chem. 1997; 62: 88
- 3e Ye Y, Zheng Y, Xu GY, Liu LZ. Heteroat. Chem. 2003; 14: 254
- 3f Kanemasa S, Matsuda H, Kamimura A, Kakinami T. Tetrahedron 2000; 56: 1057
- 3g Kumar V, Kaushik MP. Tetrahedron Lett. 2006; 47: 1457
- 3h Dubrovskiy AV, Larock RC. Org. Lett. 2010; 12: 1180
- 3i Minakata S, Okumura S, Nagamachi T, Takeda Y. Org. Lett. 2011; 13: 2966
- 4a Das B, Holla H, Mahender G, Banerjee J, Reddy MR. Tetrahedron Lett. 2004; 45: 7347
- 4b Mendelsohn BA, Lee S, Kim S, Teyssier F, Aulakh VS, Ciufolini MA. Org. Lett. 2009; 11: 1539
- 4c Jawalekar AM, Reubsaet E, Rutjes FP. J. T, van Delft FL. Chem. Commun. 2011; 47: 3198
- 5a Ochiai M, Takeuchi Y, Katayama T, Sueda T, Miyamoto K. J. Am. Chem. Soc. 2005; 127: 12244
- 5b Dohi T, Maruyama A, Yoshimura M, Morimoto K, Tohma H, Kita Y. Angew. Chem. Int. Ed. 2005; 44: 6193
- 5c Richardson RD, Wirth T. Angew. Chem. Int. Ed. 2006; 45: 4402
- 5d Dohi T, Minamitsuji Y, Maruyama A, Hirose S, Kita Y. Org. Lett. 2008; 10: 3559
- 5e Ochiai M. Chem. Rec. 2007; 7: 12
- 5f Uyanik M, Ishihara K. Chem. Commun. 2009; 2086
- 5g Dohi T, Kita Y. Chem. Commun. 2009; 2073
- 5h Liu H.-G, Tan C.-H. Tetrahedron Lett. 2007; 48: 8220
- 6a Yoshimura A, Zhu CJ, Middleton KR, Todora AD, Kastern BJ, Maskaev AV, Zhdankin VV. Chem. Commun. 2013; 49: 4800
- 6b Yoshimura A, Middleton KR, Todora AD, Kastern BJ, Koski SR, Maskaev AV, Zhdankin VV. Org. Lett. 2013; 15: 4010
- 7 Tokizane M, Sato K, Ohta T, Ito Y. Tetrahedron: Asymmetry 2008; 19: 2519
- 8 Franz JE, Pearl HK. J. Org. Chem. 1976; 41: 1296
- 9 Kim BH. Synth. Commun. 1987; 17: 1199
- 10 Trepanier DL, Faith HF, Eble JN. J. Med. Chem. 1970; 13: 729
- 11 Wakefield BJ In Science of Synthesis, Houben–Weyl Methods of Molecular Transformations . Vol. 11. Schaumann E. Georg Thieme; Stuttgart: 2002: 229
- 12 Biswanath D, Harish H, Yallamalla S, Katta V. Indian J. Heterocycl. Chem. 2007; 17: 1
- 13 Zlatopolskiy BD, Kandler R, Kobus D, Mottaghyac FM, Neumaier B. Chem. Commun. 2012; 48: 7134