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Green Chemistry Letters and Reviews Volume 6, 2013 - Issue 1
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RESEARCH LETTERS

DMF mediated Henry reaction of isatins: an efficient synthesis of 3-hydroxy-2-oxindole

Harshadas M. Meshram Organic Chemistry Division – I, Indian Institute of Chemical Technology, Hyderabad, 500 007, IndiaCorrespondence[email protected]
,
Pramod B. Thakur Organic Chemistry Division – I, Indian Institute of Chemical Technology, Hyderabad, 500 007, India
,
Madhu B. Bejjam Organic Chemistry Division – I, Indian Institute of Chemical Technology, Hyderabad, 500 007, India
&
Vikas M. Bangade Organic Chemistry Division – I, Indian Institute of Chemical Technology, Hyderabad, 500 007, India
Pages 19-43 | Received 07 Dec 2011, Accepted 11 May 2012, Published online: 28 Aug 2012

References

  • Kamano , Y. ; Zhang , H.P. ; Ichihara , Y. ; Kizu , H. ; Komiyama , K. ; Pettit , G.R. Tetrahedron. Lett . 1995 , 36 , 2783 – 2784 .
  • Kohno , J. ; Koguchi , Y. ; Nishio , M. ; Nakao , K. ; Kuroda , M. ; Shimizu , R. ; Ohnuki , T. ; Komatsubara , S. J. Org. Chem . 2000 , 65 , 990 – 995 .
  • Gan , C.Y. ; Kam , T.S. Tetrahedron. Lett . 2009 , 50 , 1059 – 1061 .
  • Tokunaga , T. ; Hume , W.E. ; Umezome , T. ; Okazaki , K. ; Ueki , Y. ; Kumagai , K. ; Hourai , S. ; Nagamine , J. ; Seki , H. ; Taiji , M. ; Noguchi , H. ; Nagata , R. J. Med. Chem . 2001 , 44 , 4641 – 4649 .
  • Miah , S. ; Moody , C.J. ; Richards , I.C. ; Slawin , A.M.Z. J. Chem. Soc., Perkin Trans. 1 , 1997 , 16 , 2405 – 2412 .
  • Frechard , A. ; Fabre , N. ; Pean , C. ; Montaut , S. ; Fauvel , M.T. ; Rollin , P. ; Fouraste , I. Tetrahedron Lett . 2001 , 42 , 9015 – 9017 .
  • Jimenez , J.I. ; Huber , U. ; Moore , R.E. ; Patterson , G.M.L. J. Nat. Prod . 1999 , 62 , 569 – 572 .
  • Lin , S. ; Yang , Z.Q. ; Kwok , B.H.B. ; Koldobskiy , M. ; Crews , C.M. ; Danishefsky , S.J. J. Am. Chem. Soc . 2004 , 126 , 6347 – 6355 .
  • Suzuki , H. ; Morita , H. ; Shiro , M. ; Kobayashi , J. Tetrahedron . 2004 , 60 , 2489 – 2495 .
  • Monde , K. ; Sasaki , K. ; Shirata , A. ; Takasugi , M. Phytochemistry . 1991 , 30 , 2915 – 2917 .
  • Suchy , M. ; Kutschy , P. ; Monde , K. ; Goto , H. ; Harada , N. ; Takasugi , M. ; Dzurilla , M. ; Balentova , E. J. Org. Chem . 2001 , 66 , 3940 – 3947 .
  • Goehring , R.R. ; Sachdeva , Y.P. ; Pisipati , J.S. ; Sleevi , M.C. ; Wolfe , J.F. J. Am. Chem. Soc . 1985 , 107 , 435 – 443 .
  • Popp , F.D. J. Heterocycl. Chem . 1984 , 21 , 1367 – 1368 .
  • Pajouhesh , H. ; Parsons , R. ; Popp , F.D. J. Pharm. Sci . 1983 , 72 , 318 – 321 .
  • Tokunaga , T. ; Hume , W.E. ; Nagamine , J. ; Kawamura , T. ; Taiji , M. ; Nagata , R. Bioorg. Med. Chem. Lett . 2005 , 15 , 1789 – 1792 .
  • Yong , S.R. ; Ung , A.T. ; Pyne , S.G. ; Skelton , B.W. ; White , A.H. Tetrahedron . 2007 , 63 , 5579 – 5586 .
  • Berensa , U. ; Brown , J.M. ; Long , J. ; Seike , R. Tetrahedron: Asymmetry . 1996 , 7 , 285 – 292 .
  • Garnick , R.L. ; LeQuesne , P.W. J. Am. Chem. Soc . 1978 , 100 , 4213 – 4219 .
  • Sakai , S. ; Aimi , N. ; Yamaguchi , K. ; Yamanaka , E. ; Haginiwa , J. J. Chem. Soc. Perkin Trans. 1 , 1982 , 3 , 1257 – 1262 .
  • Cui , C.B. ; Kakeya , H. ; Osada , H. Tetrahedron . 1996 , 52 , 12651 – 12666 ; Cui, C.B.; Kakeya, H.; Osada, H. J. Antibiot. 1996, 49, 832 835 .
  • Pedras , M.S.C. ; Ahiahonu , P.W.K. J. Chem. Ecol . 2004 , 30 , 2163 – 2179 .
  • Elderfield , R.C. ; Gilman , R.E. Phytochemistry . 1972 , 11 , 339 – 343 .
  • Sakai , S. ; Aimi , N. ; Yamaguchi , K. ; Ohhira , H. ; Hori , K. ; Haginiwa , J. Tetrahedron Lett . 1975 , 16 , 715 – 718 .
  • Aimi , N. ; Yamaguchi , K. ; Sakai , S. ; Haginiwa , J. ; Kubo , A. Chem. Pharm. Bull . 1978 , 26 , 3444 – 3449 .
  • Ghedira , K. ; Zeches-Hanrot , M. ; Richard , B. ; Massiot , G. ; Le Men-Oliver , L. ; Sevener , T. ; Goh , S.H. Phytochemistry . 1988 , 27 , 3955 – 3961 .
  • Jossang , A. ; Jossang , P. ; Hadi , H.A. ; Sevenet , T. ; Bodo , B. J. Org. Chem . 1991 , 56 , 6527 – 6530 .
  • Wong , W.H. ; Lim , P.B. ; Chuah , C.H. Phytochemistry . 1996 , 41 , 313 .
  • Anderton , N. ; Cockrum , P.A. ; Colegate , S.M. ; Edgar , J.A. ; Flower , K. ; Vit , I. ; Willing , R.I. Phytochemistry . 1998 , 48 , 437 – 439 .
  • Henry , L. Compt. Rend . 1895 , 120 , 1265 .
  • Conn , W.R. ; Lindwall , H.G. J. Am. Chem. Soc . 1936 , 58 , 1236 – 1239 .
  • Michail , N.E. ; Alexey , I.I. ; Valentina , M.M. ; Fructuoso , B. ; Belen , B. Tetrahedron . 2008 , 64 , 5915 – 5919 .
  • For some selected examples about reactions under catalyst-free condition see : Watahiki , T. ; Matsuzaki , M. ; Oriyama , T. Green Chem . 2003 , 5 , 82 – 84 .
  • Watahiki , T. ; Ohba , S. ; Oriyama , T. Org. Lett . 2003 , 5 , 2679 – 2681 .
  • Iwanami , K. ; Hinakubo , Y. ; Oriyama , T. Tetrahedron Lett . 2005 , 46 , 5881 – 5883 .
  • Iwanami , K. ; Oriyama , T. Synlett . 2006 , 1 , 112 – 114 .
  • Khatik , G.L. ; Kumar , R. ; Chakraborti , A.K. Org. Lett . 2006 , 8 , 2433 – 2436 .
  • Oriyama , T. ; Aoyagi , M. ; Iwanami , K. Chem. Lett . 2007 , 36 , 612 – 613 .
  • Zhang , M. ; Jiang , H.F. ; Liu , H.L. ; Zhu , Q.H. Org. Lett . 2007 , 9 , 4111 – 4113 .
  • Chen , W.B. ; Liao , Y.H. ; Du , X.L. ; Zhang , X.M. ; Yuan , W.C. Green Chem . 2009 , 11 , 1465 – 1476 .
  • Meshram , H.M. ; Ramesh , P. ; Reddy , B.C. ; Shreedhar , B. ; Yadav , J.S. Tetrahedron . 2011 , 67 , 3150 – 3155 .
  • Meshram , H.M. ; Kumar , D.A. ; Reddy , B.C. ; Ramesh , P. Synth. Commun . 2010 , 40 , 39 – 45 .
  • Meshram , H.M. ; Ramesh , P. ; Kumar , A.S. ; Swetha , A. Tetrahedron Lett . 2011 , 52 , 5862 – 5864 .
  • Popp , F.D. Adv. Heterocycl. Chem . 1975 , 18 , 1 – 58 .
  • da Silva , J.F.M. ; Garden , S.J. ; Pinto , A.C. J. Braz. Chem. Soc . 2001 , 12 , 273 – 324 .
  • The powdered molecular sieves 4 Å were activated by placing the powder under vacuum and heating with the flame of gas burner .
  • Bug , T. ; Tadeusz , L. ; Herbert , M. J. Org. Chem . 2004 , 69 , 7565 – 7576 .
  • The solvents used in this work were all carefully dried and distilled freshly before use. DMF was dried and freshly distilled from calcium hydride before use. We have Added nearly 8 gm calcium hydride in to 100 ml DMF (SRL make, AR grade, min. 99% purity) and stirred for 5 hours under nitrogen atmosphere. Then calcium hydride was decanted and DMF was distilled under nitrogen at 60°C, by using approximately 30 mmHg vacuums. This distilled DMF was stored on powdered 4 Å molecular sieves and used as it is for the reactions .
  • Marcelli , T. ; van der Haas , R.N.S. ; van Maarseveen , J.H. ; Hiemstra , H. Angew. Chem. Int. Ed . 2006 , 45 , 929 – 931 .

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