Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2010(11): 1771-1776
DOI: 10.1055/s-0029-1218730
DOI: 10.1055/s-0029-1218730
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New YorkBromodimethylsulfonium Bromide-ZnCl2: A Mild and Efficient Catalytic System for Beckmann Rearrangement
Further Information
Received
23 February 2010
Publication Date:
09 April 2010 (online)
Publication History
Publication Date:
09 April 2010 (online)
Abstract
Bromodimethylsulfonium bromide, in combination with zinc chloride, has been shown to be an excellent catalytic system for liquid-phase Beckmann rearrangement of various ketoximes into the corresponding amides/lactams in acetonitrile at reflux temperature with good to excellent yields.
Key words
Beckmann rearrangement - ketoximes - amides - bromodimethylsulfonium bromide (BDMS) - catalytic process - Lewis acids
- 1a
Choudhury LH.Pravin T.Khan AT. Tetrahedron 2009, 65: 9513 ; and references cited therein - 1b
Olah GA.Vankar YD.Arvanaghi M.Surya Prakash GK. Synthesis 1979, 720 - 1c
Meerwein H.Zenner KF.Gipp R. Justus Liebigs Ann. Chem. 1965, 67: 688 - 1d
Choudhury LH. Synlett 2006, 1619 - 1e
Furukawa N.Inoue T.Aida T.Oae S. J. Chem. Soc., Chem. Commun. 1973, 212a - 2a
Xiong D.-C.Zhang L.-H.Ye X.-S. Adv. Synth. Catal. 2008, 305: 1696 - 2b
Khan AT.Parvin T.Gazi S.Choudhury LH. Tetrahedron Lett. 2007, 48: 3805 - 2c
Khan AT.Parvin T.Choudhury LH. Eur. J. Org. Chem. 2008, 834 - 2d
Khan AT.Parvin T.Choudhury LH. J. Org. Chem. 2008, 73: 8398 - 2e
Das B.Holla H.Srinivas Y. Tetrahedron Lett. 2007, 48: 61 - 3a
Das B.Srinivas Y.Sudhakar C.Ravikanth B.
J. Chem. Res. 2008, 188 - 3b
Das B.Srinivas Y.Holla H.Laxminarayana K.Narender R. Tetrahedron Lett. 2007, 48: 6681 - 3c
Jiang B.Dou Y.Xu X.Xu M. Org. Lett. 2008, 10: 593 - 4a
Gawly RE. Org. React. 1988, 35: 1 - 4b
Smith MB.March J. In Advanced Organic Chemistry 5th ed.: John Wiley & Sons; New York: 2001. p.1415 ; and references therein - 5a
Narasaka K.Kusama H.Yamashita Y.Sato H. Chem. Lett. 1993, 489 - 5b
Iranpoor N.Firouzabadi H.Aghapour G. Synth. Commun. 2002, 32: 2535 - 5c
De KS. Synth. Commun. 2005, 34: 3431 - 5d
Izumi Y. Chem. Lett. 1990, 2171 - 5e
Antikumar S.Chandrasekhar S. Tetrahedron Lett. 2000, 41: 5427 - 5f
Ren RX.Zueva LD.Ou W. Tetrahedron Lett. 2001, 42: 8441 - 5g
Sato H.Yoshika H.Izumi Y. J. Mol. Catal. A: Chem. 1999, 149: 25 - 6a
Yadav JS.Reddy BVS.Madhavi AV.Ganesh YSS. J. Chem. Res., Synop. 2002, 5: 236 - 6b
De Luca L.Giacomelli G.Porcheddu A. J. Org. Chem. 2002, 67: 6272 - 6c
Yan P.Batamack P.Prakash GKS.Olah GA. Catal. Lett. 2005, 103: 165 - 6d
Arisawa M.Yamaguchi M. Org. Lett. 2001, 3: 311 - 6e
Boruah M.Konwar D. J. Org. Chem. 2002, 67: 7138 - 6f
Chandrasekhar S.Gopalaiah K. Tetrahedron Lett. 2002, 43: 2455 - 6g
Furuya Y.Ishihara K.Yamamoto H. J. Am. Chem. Soc. 2005, 127: 11240 - 6h
Wang B.Gu Y.Luo C.Yang T.Yang L.Suo J. Tetrahedron Lett. 2004, 45: 3369 - 7a
Hashimoto M.Obora Y.Sakaguchi S.Ishii Y.
J. Org. Chem. 2008, 73: 2894 - 7b
Li D.Shi F.Guo S.Deng Y. Tetrahedron Lett. 2005, 46: 671 - 7c
Zhu M.Cha C.Deng W.Shi X. Tetrahedron Lett. 2006, 47: 4861 - 7d
Sardarian AR.Shahsavari-Fard Z.Shahsavari HR.Ebrahimi Z. Tetrahedron Lett. 2007, 48: 2639 - 7e
Ramalingan C.Park Y.-T. J. Org. Chem. 2007, 72: 4536 - 7f
Su WK.Zhang Y.Li JJ.Li P. Org. Prep. Proced. Int. 2008, 40: 543 - 7g
Pi H.-J.Dong J.-D.An N.Du W.Deng W.-P. Tetrahedron 2009, 65: 7790 - 7h
Ronchin L.Vavasori A. J. Mol. Catal. A: Chem. 2009, 313: 22 - 7i
Xiao L.-f.Xia C.-G.Chen J. Tetrahedron Lett. 2007, 48: 7218 - 8a
Boero M.Ikeshoji T.Liew CC.Terakura K.Parrinello M. J. Am. Chem. Soc. 2004, 126: 6280 - 8b
Ikushima Y.Hatakeda K.Sato M.Sato O.Arai M. Chem. Commun. 2002, 19: 2208 - 8c
Ikushima Y.Hatakeda K.Sato O.Yokoyama T.Arai M. Angew. Chem. Int. Ed. 1999, 38: 2910 - 8d
Ikushima Y.Sato O.Sato M.Hatakeda K.Arai M. Chem. Eng. Sci. 2003, 58: 935 - 9a
Liu X.Xiao L.Wu H.Li Z.Chen J.Xia C. Catal. Commun. 2009, 10: 424 - 9b
Zicmanis A.Katkevica S.Mekss P. Catal. Commun. 2009, 10: 614 - 9c
Yadav LDS.Garima .Srivastava VP. Tetrahedron Lett. 2010, 51: 739 - 9d
Peng J.Deng Y. Tetrahedron Lett. 2001, 42: 403 - 9e
Gui J.Deng Y.Hu Z.Sun Z. Tetrahedron Lett. 2004, 45: 2682 - 9f
Guo S.Du Z.Zhang S.Li D.Li Z.Deng Y. Green Chem. 2006, 8: 296 - 9g
Betti C.Landini D.Maia A.Pasi M. Synlett 2008, 908 - 10a
Ghiaci M.Abbaspur A.Kalbasi R. Appl. Catal., A 2005, 287: 83 - 10b
Forni L.Fornasari G.Giordano G.Lucarelli C.Katovic A.Trifiro F.Perri C.Nagy JB. Phys. Chem. Chem. Phys. 2004, 6: 1842 - 10c
Mao D.Lu G.Chen Q. Appl. Catal., A 2005, 279: 145 - 10d
Dongare MK.Bhagwat VV.Ramana CV.Gurjar MK. Tetrahedron Lett. 2004, 45: 4759 - 10e
Mao D.Chen Q.Lu G. Appl. Catal., A 2003, 244: 273 - 10f
Kim SJ.Jung KD.Joo OS.Kim EJ.Kang TB. Appl. Catal., A 2004, 266: 173 - 11a
Chandrasekhar S.Gopalaiah K. Tetrahedron Lett. 2003, 44: 7437 - 11b
Chandrasekhar S.Gopalaiah K. Tetrahedron Lett. 2003, 44: 755 - 12a
Yadav LDS.Srivastava VP.Patel R. Tetrahedron Lett. 2009, 50: 5532 - 12b
Yadav LDS.Singh S.Rai VK. Green Chem. 2009, 11: 878 - 12c
Yadav LDS.Patel R.Srivastava VP. Tetrahedron Lett. 2009, 50: 1335 - 12d
Yadav LDS.Rai A. Synthesis 2009, 2802 - 12e
Yadav LDS.Patel R.Srivastava VP. Synlett 2008, 1789 - 13a
Majetich G.Hicks R.Reister S. J. Org. Chem. 1997, 62: 4321 - 13b
Mislow K.Simmons T.Melillo J.Ternay A. J. Am. Chem. Soc. 1964, 86: 1452 - 13c
Harrowven DC.Dennison ST. Tetrahedron Lett. 1993, 34: 3323