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Synthetic Communications

An International Journal for Rapid Communication of Synthetic Organic Chemistry

Volume 44, 2014 - Issue 13

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Synthesis of 4-Diarylamino-3-iodo-2(5H)-furanones via the Simultaneous α-Iodination and N^β-Arylation by an Efficient Difunctionalizable Transfer Reagent PhI(OAc)₂

Fuling Xue School of Chemistry and Environment, South China Normal University, Key Laboratory of Theoretical Chemistry of Environment, Ministry of Education, Guangzhou, China

Pai Peng School of Chemistry and Environment, South China Normal University, Key Laboratory of Theoretical Chemistry of Environment, Ministry of Education, Guangzhou, China

Jie Shi School of Chemistry and Environment, South China Normal University, Key Laboratory of Theoretical Chemistry of Environment, Ministry of Education, Guangzhou, China

Mingli Zhong School of Chemistry and Environment, South China Normal University, Key Laboratory of Theoretical Chemistry of Environment, Ministry of Education, Guangzhou, China

Zhaoyang Wang School of Chemistry and Environment, South China Normal University, Key Laboratory of Theoretical Chemistry of Environment, Ministry of Education, Guangzhou, ChinaCorrespondence[email protected]; [email protected]

Pages 1944-1956 | Received 26 Nov 2013, Published online: 29 May 2014

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https://doi.org/10.1080/00397911.2013.879899
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REFERENCES

Zhdankin , V. V. ; Stang , P. J. Chem. Rev. 2008 , 108 , 5299 – 5358 .
PubMed Web of Science ®Google Scholar
Varvoglis , A. Tetrahedron 1997 , 53 , 1179 – 1255 .
Web of Science ®Google Scholar
Celik , M. ; Alp , C. ; Coskun , B. ; Gueltekin , M. S. ; Balci , M. Tetrahedron Lett. 2006 , 47 , 3659 – 3663 .
Web of Science ®Google Scholar
Roben , C. ; Souto , J. A. ; Escudero-Adan , E. C. ; Muniz , K. Org. Lett. 2013 , 15 , 1008 – 1011 .
PubMed Web of Science ®Google Scholar
Papoutsis , I. ; Spyroudis , S. ; Varvoglis , A. Tetrahedron Lett. 1996 , 37 , 913 – 916 .
Web of Science ®Google Scholar
Papoutsis , I. ; Spyroudis , S. ; Varvoglis , A. J. Heterocycl. Chem. 1996 , 33 , 579 – 581 .
Web of Science ®Google Scholar
Koposov , A. Y. ; Boyarskikh , V. V. ; Zhdankin , V. V. Org. Lett. 2004 , 6 , 3613 – 3615 .
PubMed Web of Science ®Google Scholar
Janson , P. G. ; Ghoneim , I. ; Ilchenko , N. O. ; Szabo , K. J. Org. Lett. 2012 , 14 , 2882 – 2885 .
PubMed Web of Science ®Google Scholar
Ji , X.-C. ; Huang , H.-W. ; Wu , W.-Q. ; Jiang , H.-F. J. Am. Chem. Soc. 2013 , 135 , 5286 – 5289 .
PubMed Web of Science ®Google Scholar
Zeng , Y.-W. ; Zhang , L.-J. ; Zhao , Y.-C. ; Ni , C.-F. ; Zhao , J.-W. ; Hu , J.-B. J. Am. Chem. Soc. 2013 , 135 , 2955 – 2958 .
PubMed Web of Science ®Google Scholar
Tingoli , M. ; Tiecco , M. ; Chianelli , D. ; Balducci , R. ; Temperini , A. J. Org. Chem. 1991 , 56 , 6809 – 6813 .
Web of Science ®Google Scholar
Magnus , P. ; Roe , M. B. Tetrahedron Lett. 1996 , 37 , 303 – 306 .
Web of Science ®Google Scholar
Mironov , Y. V. ; Sherman , A. A. ; Nifantiev , N. E. Tetrahedron Lett. 2004 , 45 , 9107 – 9110 .
Web of Science ®Google Scholar
Yu , L. ; Chen , B. ; Huang , X. Tetrahedron Lett. 2007, 48, 925–927.
Web of Science ®Google Scholar
Martínez , C. ; Wu , Y.-C. ; Weinstein , A. B. ; Stahl , S. S. ; Liu , G.-S. ; Muñiz , K. J. Org. Chem. 2013 , 78 , 6309 – 6315 .
PubMed Web of Science ®Google Scholar
Fumagalli , G. ; Boyd , S. ; Greaney , M. F. Org. Lett. 2013 , 15 , 4398 – 4401 .
PubMed Web of Science ®Google Scholar
Benjahad , A. ; Guillemont , J. ; Andries , K. ; Nguyen , C. H. ; Grierson , D. S. Bioorg. Med. Chem. Lett. 2003 , 13 , 4309 – 4312 .
PubMed Web of Science ®Google Scholar
Benjahad , A. ; Oumouch , S. ; Guillemont , J. ; Pasquier , E. ; Mabire , D. ; Andries , K. ; Nguyen , C. H. ; Grierson , D. S. Bioorg. Med. Chem. Lett. 2007 , 17 , 712 – 716 .
PubMed Web of Science ®Google Scholar
Collins , B. S. L. ; Suero , M. G. ; Gaunt , M. J. Angew. Chem. Int. Ed. 2012 , 51 , 5799 – 5802 .
Google Scholar
He , Z.-B. ; Hu , M.-Y. ; Luo , T. ; Li , L.-C. ; Hu , J.-B. Angew. Chem. Int. Ed. 2012 , 51 , 11545 – 11547 .
PubMed Web of Science ®Google Scholar
Souto , J. A. ; Becker , P. ; Iglesias , Á. ; Muñiz , K. J. Am. Chem. Soc. 2012 , 134 , 15505 – 15511 .
PubMed Web of Science ®Google Scholar
Wang , X. ; Ye , Y.-X. ; Ji , G.-J. ; Xu , Y. ; Zhang , S.-N. ; Feng , J.-J. ; Zhang , Y. ; Wang , J.-B. Org. Lett. 2013 , 15 , 3730 – 3733 .
PubMed Web of Science ®Google Scholar
Fan , R.-H. ; Sun , Y. ; Ye , Y. Org. Lett. 2009 , 11 , 5174 – 5177 .
PubMed Web of Science ®Google Scholar
Shibuya , M. ; Shibuta , T. ; Fukuda , H. ; Iwabuchi , Y. Org. Lett. 2012 , 14 , 5010 – 5013 .
PubMed Web of Science ®Google Scholar
Havare , N. ; Plattner , D. A. Org. Lett. 2012 , 14 , 5078 – 5081 .
PubMed Web of Science ®Google Scholar
Thirunavukkarasu , V. S. ; Ackermann , L. Org. Lett. 2012 , 14 , 6206 – 6209 .
PubMed Web of Science ®Google Scholar
Liang , D.-D. ; He , Y.-M. ; Liu , L.-Y. ; Zhu , Q. Org. Lett. 2013 , 15 , 3476 – 3479 .
PubMed Web of Science ®Google Scholar
Sun , Y. ; Fan , R.-H. Chem. Commun. 2010 , 46 , 6834 – 6836 .
PubMed Web of Science ®Google Scholar
Sun , Y. ; Gan , J.-H. ; Fan , R.-H. Adv. Synth. Catal. 2011 , 353 , 1735 – 1740 .
Web of Science ®Google Scholar
Mei , T.-S. ; Leow , D. ; Xiao , H. ; Laforteza , B. N. ; Yu , J.-Q. Org. Lett. 2013 , 15 , 3058 – 3061 .
PubMed Web of Science ®Google Scholar
Yu , W. ; Du , Y. ; Zhao , K. Org. Lett. 2009 , 11 , 2417 – 2420 .
PubMed Web of Science ®Google Scholar
Bian , M. ; Wang , Z. ; Xiong , X.-C. ; Sun , Y. ; Matera , C. ; Nicolaou , K. C. ; Li , A. J. Am. Chem. Soc. 2012 , 134 , 8078 – 8081 .
PubMed Web of Science ®Google Scholar
Bao , M.-F. ; Zeng , C.-X. ; Qu , Y. ; Kong , L.-M. ; Liu , Y.-P. ; Gai , X.-H. ; Luo , X.-D. Nat. Prod. Bioprospect. 2012 , 2 , 121 – 125 .
Google Scholar
Lin , H.-Y. ; Snider , B. B. J. Org. Chem. 2012 , 77 , 4832 – 4836 .
PubMed Web of Science ®Google Scholar
Rosu , T. ; Pahontu , E. ; Ilies , D. C. ; Georgescu , R. ; Mocanu , M. ; Leabu , M. ; Shova , S. ; Gulea , A. Eur. J. Med. Chem. 2012 , 53 , 380 – 389 .
PubMed Web of Science ®Google Scholar
Stevenson , R. J. ; Denny , W. A. ; Tercel , M. ; Pruijn , F. B. ; Ashoorzadeh , A. J. Med. Chem. 2012 , 55 , 2780 – 2802 .
PubMed Web of Science ®Google Scholar
Mezlova , M. ; Aaron , J. J. ; Svoboda , J. ; Adenier , A. ; Maurel , F. ; Chane-Ching , K. J. Electroanal. Chem. 2005 , 581 , 93 – 103 .
Web of Science ®Google Scholar
Lattmann , E. ; Dunn , S. ; Niamsanit , S. ; Sattayasai , N. Bioorg. Med. Chem. Lett. 2005 , 15 , 919 – 921 .
PubMed Web of Science ®Google Scholar
Hikawczuk , V. E. J. ; Saad , J. R. ; Giordano , O. S. ; Garcia , C. ; Martin , T. ; Martin , V. S. ; Sosa , M. E. ; Tonn , C. E. J. Nat. Prod. 2008 , 71 , 190 – 194 .
PubMed Web of Science ®Google Scholar
Trost , B. M. ; Burns , A. C. ; Bartlett , M. J. ; Tautz , T. ; Weiss , A. H. J. Am. Chem. Soc. 2012 , 134 , 1474 – 1477 .
PubMed Web of Science ®Google Scholar
Zhang , Y.-A. ; Liu , Q. ; Wang , C. ; Jia , Y.-X. Org. Lett. 2013 , 15 , 3662 – 3665 .
PubMed Web of Science ®Google Scholar
Gassama , A. ; Ernenwein , C. ; Hoffmann , N. Green Chem. 2010 , 12 , 859 – 865 .
Web of Science ®Google Scholar
Ube , H. ; Shimada , N. ; Terada , M. Angew. Chem. Int. Ed. 2010 , 49 , 1858 – 1861 .
PubMed Web of Science ®Google Scholar
Hickmann , V. ; Kondoh , A. ; Gabor , B. ; Alcarazo , M. ; Furstner , A. J. Am. Chem. Soc. 2011 , 133 , 13471 – 13480 .
PubMed Web of Science ®Google Scholar
Spence , J. T. J. ; George , J. H. Org. Lett. 2013 , 15 , 3891 – 3893 .
PubMed Web of Science ®Google Scholar
Du , Y. ; Xu , L.-W. ; Shimizu , Y. ; Oisaki , K. ; Kanai , M. ; Shibasaki , M. J. Am. Chem. Soc. 2008 , 130 , 16146 – 16147 .
PubMed Web of Science ®Google Scholar
Luo , Y. ; Carnell , A. J. Angew. Chem. Int. Ed. 2010 , 49 , 2750 – 2754 .
PubMed Web of Science ®Google Scholar
Luo , J. ; Wang , H.-F. ; Han , X. ; Xu , L.-W. ; Kwiatkowski , J. ; Huang , K.-W. ; Lu , Y.-X. Angew. Chem. Int. Ed. 2011, 50, 1861–1864.
PubMed Web of Science ®Google Scholar
Li , J.-X. ; Liang , H.-R. ; Wang , Z.-Y. ; Fu , J.-H. Monatsh. Chem. 2011 , 142 , 507 – 513 .
Web of Science ®Google Scholar
Lakshmi , V. ; Srivastava , S. ; Mishra , S. K. ; Srivastava , M. N. ; Srivastava , K. ; Puri , S. K. Nat. Prod. Res. 2012 , 26 , 1012 – 1015 .
PubMed Web of Science ®Google Scholar
Yavorskyy , A. ; Shvydkiv , O. ; Hoffmann , N. ; Nolan , K. ; Oelgemoller , M. Org. Lett. 2012 , 14 , 4342 – 4345 .
PubMed Web of Science ®Google Scholar
Tan , Y.-H. ; Li , J.-X. ; Xue , F.-L. ; Qi , J. ; Wang , Z.-Y. Tetrahedron 2012 , 68 , 2827 – 2843 .
Web of Science ®Google Scholar
Yuan , C.-C. ; Du , B. ; Yang , L. ; Liu , B. J. Am. Chem. Soc. 2013 , 135 , 9291 – 9294 .
PubMed Web of Science ®Google Scholar
Xue , X.-S. ; Li , X. ; Yu , A. ; Yang , C. ; Song , C. ; Cheng , J.-P. J. Am. Chem. Soc. 2013 , 135 , 7462 – 7473 .
PubMed Web of Science ®Google Scholar
Yin , L. ; Takada , H. ; Kumagai , N. ; Shibasaki , M. Angew. Chem. Int. Ed. 2013 , 52 , 7310 – 7313 .
PubMed Web of Science ®Google Scholar
Huo , J.-P. ; Luo , J.-C. ; Wu , W. ; Xiong , J.-F. ; Mo , G.-Z. ; Wang , Z.-Y. Ind. Eng. Chem. Res. 2013 , 52 , 11850 – 11857 .
Web of Science ®Google Scholar
(a) Xue , F.-L. ; Li , J.-X. ; Wang , Z.-Y. ; Xiong , J.-F. ; Li , D. Res. Chem. Intermed. 2013 , 39 , 1153 – 1168 ; (b) Xue , F.-L. ; Qi , J. ; Peng , P. ; Mo , G.-Z. ; Wang , Z.-Y. Lett. Org. Chem. 2014 , 11, 64–79 .
Web of Science ®Google Scholar
Huo , J.-P. ; Deng , G.-H. ; Wu , W. ; Xiong , J.-F. ; Zhong , M.-L. ; Wang , Z.-Y. Macromol. Rapid Commun. 2013 , 34 , 1779 – 1784 .
PubMed Web of Science ®Google Scholar
Reddy , M. S. ; Thirupathi , N. ; Babu , M. H. ; Puri , S. J. Org. Chem. 2013 , 78 , 5878 – 5888 .
PubMed Web of Science ®Google Scholar
Ma , S.-M. ; Shi , Z.-J. ; Yu , Z.-Q. Tetrahedron 1999 , 55 , 12137 – 12148 .
Web of Science ®Google Scholar
Carter , N. B. ; Mabon , R. ; Richecoeur , A. M. E. ; Sweeney , J. B. Tetrahedron 2002 , 58 , 9117 – 9129 .
Web of Science ®Google Scholar
Ma , S.-M. ; Wu , B. ; Shi , Z.-J. J. Org. Chem. 2004 , 69 , 1429 – 1431 .
PubMed Web of Science ®Google Scholar
Zhang , X.-X. ; Larock , R. C. J. Am. Chem. Soc. 2005 , 127 , 12230 – 12231 .
PubMed Web of Science ®Google Scholar
Fu , C.-L. ; Ma , S.-M. Eur. J. Org. Chem. 2005 , 3942 – 3945 .
Web of Science ®Google Scholar
Boukouvalas , J. ; Loach , R. P. J. Org. Chem. 2008 , 73 , 8109 – 8112 .
PubMed Web of Science ®Google Scholar
Tang , B.-X. ; Yin , Q. ; Tang , R.-Y. ; Li , J.-H. J. Org. Chem. 2008 , 73 , 9008 – 9011 .
PubMed Web of Science ®Google Scholar
Chen , Y. ; Ju , T. ; Wang , J.-W. ; Yu , W.-Q. ; Du , Y.-F. ; Zhao , K. Synlett 2010 , 231 – 234 .
Web of Science ®Google Scholar
Lattmann , E. ; Sattayasai , N. ; Schwalbe , C. S. ; Niamsanit , S. ; Billington , D. C. ; Lattmann , P. ; Langley , C. A. ; Singh , H. ; Dunn , S. Curr. Drug Disc. Technol. 2006 , 3 , 125 – 134 .
PubMedGoogle Scholar
Labruere , R. ; Gautier , B. ; Testud , M. ; Seguin , J. ; Lenoir , C. ; Desbene-Finck , S. ; Helissey , P. ; Garbay , C. ; Chabot , G. G. ; Vidal , M. ; Giorgi-Renault , S. Chem. Med. Chem. 2010 , 5 , 2016 – 2025 .
Web of Science ®Google Scholar
Semenova , M. N. ; Kiselyov , A. S. ; Tsyganov , D. V. ; Konyushkin , L. D. ; Firgang , S. I. ; Semenov , R. V. ; Malyshev , O. R. ; Raihstat , M. M. ; Fuchs , F. ; Stielow , A. ; Lantow , M. ; Philchenkov , A. A. ; Zavelevich , M. P. ; Zefirov , N. S. ; Kuznetsov , S. A. ; Semenov , V. V. J. Med. Chem. 2011 , 54 , 7138 – 7149 .
PubMed Web of Science ®Google Scholar
Shi , F. ; Zeng , X.-N. ; Zhang , G. ; Ma , N. ; Jiang , B. ; Tu , S.-J. Bioorg. Med. Chem. Lett. 2011 , 21 , 7119 – 7123 .
PubMed Web of Science ®Google Scholar
Mo , Y.-Q. ; Wang , Z.-Y. ; Mei , W.-J. ; Fu , J.-H. ; Tan , Y.-H. ; Luo , S.-H. Monatsh. Chem. 2012 , 143 , 443 – 453 .
Web of Science ®Google Scholar
Papoutsis , I. ; Spyroudis , S. ; Varvoglis , A. ; Raptopoulou , C. Tetrahedron 1997 , 53 , 6097 – 6112 .
Web of Science ®Google Scholar
Takaku , M. ; Hayashi , Y. ; Nozaki , H. Tetrahedron 1970 , 26 , 1243 – 1247 .
Web of Science ®Google Scholar
Wang , Y.-P. ; Danheiser , R. L. Tetrahedron Lett. 2011 , 52 , 2111 – 2114 .
PubMed Web of Science ®Google Scholar
Stefani , H. A. ; Amaral , M. F. Z. J. ; Manarin , F. ; Ando , R. A. ; Silva , N. C. S. ; Juaristi , E. Tetrahedron Lett. 2011 , 52 , 6883 – 6886 .
Web of Science ®Google Scholar
Mao , C.-X. ; Wang , Z.-Y. ; Tan , Y.-H. ; Xue , F.-L. Chin. J. Org. Chem. 2011 , 31 , 1377 – 1387 .
Web of Science ®Google Scholar
Sheldrick , G. M. SHELX-97, an Integrated System for Solving and Refining Crystal Structures from Diffraction Data ; University of Göttingen : Germany , 1997 .
Google Scholar
Color versions of one or more of the figures in the article can be found online at www.tandfonline.com/lsyc.
Google Scholar

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Synthesis of 4-Diarylamino-3-iodo-2(5H)-furanones via the Simultaneous α-Iodination and N^β-Arylation by an Efficient Difunctionalizable Transfer Reagent PhI(OAc)₂

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Synthesis of 4-Diarylamino-3-iodo-2(5H)-furanones via the Simultaneous α-Iodination and Nβ-Arylation by an Efficient Difunctionalizable Transfer Reagent PhI(OAc)2

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Synthesis of 4-Diarylamino-3-iodo-2(5H)-furanones via the Simultaneous α-Iodination and N^β-Arylation by an Efficient Difunctionalizable Transfer Reagent PhI(OAc)₂