Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 37, 2007 - Issue 5
179
Views
3
CrossRef citations to date
0
Altmetric
Original Articles

Efficient and Practical Route to α‐Aminocarbonylketene and α‐Cyanoketene Dithioacetals

, , , &
Pages 703-711 | Received 20 Jun 2006, Published online: 10 Mar 2007

References

  • Dieter , R. K. 1986 . α‐Oxo ketene dithioacetals and related compounds: Versatile three‐carbon synthons . Tetrahedron , 42 : 3029 – 3096 . For review; on the synthesis and application of α‐oxo ketene dithioacetals, see (a)
  • Tominga , Y. 1989 . Synthesis of heterocyclic compounds using carbon disulfide and their products . J. Heterocycl. Chem. , 26 : 1167 – 1204 .
  • Junjappa , H. , Ila , H. and Asokan , C. V. 1990 . α‐Oxoketene‐S,S‐, N,S‐ and N,N‐acetals: intermediates in organic synthesis Tetrahedron . 46 : 5423 – 5506 .
  • Kolb , M. 1990 . Ketene dithioacetals in organic synthesis: Recent developments . Synthesis , 3 : 171 – 190 .
  • Junjappa , H. and Ila , H. 1994 . Phosphorus, Sulfur Silicon Relat. Elem. , 35 : 95 – 96 .
  • Junjappa , H. , Ila , H. and Mohanta , P. K. 2001 . Progress in Heterocyclic Chemistry Edited by: Gribble , G. H. and Gilchrist , L. T. Vol. 13 , 1 – 24 . Oxford : Pergamon Press . Chapter 1
  • Kouno , R. , Okauchi , T. , Nakamura , M. , Ichikawa , J. and Minami , T. 1998 . Synthesis and synthetic utilization of α‐functionalized vinylphosphonates bearing β‐oxy or β‐thio substituents . J. Org. Chem. , 63 : 6239 – 6246 . Selected examples of phosphonoketen dithioacetals (a)
  • Minami , T. , Okauchi , T. , Matsuki , H. , Nakamura , M. , Ichikawa , J. and Ishida , M. 1996 . Synthesis and synthetic application of phosphonoketene dithioacetals: New synthesis of dithioallenes and (α‐dithiocarboxyvinyl)phosphonates . J. Org. Chem. , 61 : 8132 – 8140 .
  • Brulé , C. , Bouillon , J.‐ P. , Nicolaï , E. and Portella , C. 2003 . Fluorinated ketene dithioacetals, part 10: Synthesis of new perfluorinated (2H)‐pyridazin‐3‐ones and 3‐(alkyl‐ or arylamino) substituted pyridazines . Synthesis , 3 : 436 – 442 . Selected examples of fluorinated ketene dithioacetals (a)
  • Timoshenko , V. M. , Bouillon , J.‐ P. , Shermolovich , Y. G. and Portella , C. 2002 . Flourinated ketene dithioacetals, part IX: Synthesis and some chemical properties of new fluorinated 3H‐1,2‐dithiole‐3‐thiones . Tetrahedron Lett. , 43 : 5809 – 5812 .
  • Pfund , E. , Masson , S. , Vazeux , M. and Lequeux , T. 2004 . Syntheses of α‐fluoro‐α,β‐unsaturated thioamides and thiazolines from a fluorophosphonodithioacetate . J. Org. Chem. , 69 : 4670 – 4676 .
  • Liu , Q. , Che , G. , Yu , H. , Liu , Y. , Zhang , J. , Zhang , Q. and Dong , D. 2003 . The first nonthiolic, odorless 1,3‐propanedithiol equivalent and its application in thioacetalization . J. Org. Chem. , 68 : 9148 – 9150 .
  • Yu , H. , Liu , Q. , Yin , Y. , Fang , Q. , Zhang , J. and Dong , D. 2004 . α,α‐Diacetyl cyclic ketene dithioacetals: Odorless and efficient dithiol equivalents in thioacetalization reaction . Synlett , 6 : 999 – 1002 .
  • Dong , D. , Bi , X. , Liu , Q. and Cong , F. 2005 . [5C+1 N] Annulation: A novel synthetic strategy for functionalized 2,3‐dithydro‐4‐pyridones . Chem. Commun. , 28 : 3580 – 3582 .
  • Bi , X. , Dong , D. , Liu , Q. , Pan , W. , Zhao , L. and Li , B. 2005 . [5+1] Annulation: A synthetic strategy for highly substituted phenols and cyclohexenones . J. Am. Chem. Soc , 127 : 4578 – 4579 .
  • Wang , M. , Ai , L. , Zhang , J. , Liu , Q. and Gao , L. 2002 . Synthesis of 2‐benzylthio‐5‐phenyl‐3,4‐disubstituted thiophenes by intramolecular condensation of α‐oxo ketene dibenzyl‐thioacetals . Chin. J. Chem. , 20 : 1591 – 1597 .
  • Zhang , S. , Liu , Q. and Chen , Y. 2000 . Studies on the one‐pot reaction of active methylene compounds with 2‐bromoethanol—Preparation of α‐oxoketene cyclic O,S‐ethylene acetals . Ind. J. Chem. , 39B : 147 – 150 .
  • Yin , Y. , Wang , M. , Liu , Q. , Hu , J. , Sun , S. and Kang , J. 2005 . A C‐C bond formation reaction at the α‐carbon atom of α‐oxo ketene dithioacetals via the Baylis–Hillman type reaction . Tetrahedron Lett. , 46 : 4399 – 4402 .
  • Sun , S. , Zhang , Q. , Liu , Q. , Yin , Y. , Li , D. and Dong , D. 2005 . One‐pot synthesis of aza‐Morita–Baylis–Hilman adducts from α‐oxo ketene‐S,S‐acetals arylaldehydes and nitriles . Tetrahedron Lett. , 46 : 6271 – 6274 .
  • Fleming , F. F. and Wang , Q. 2003 . Unsaturated nitriles: Conjugate additions of carbon nucleophiles to a recalcitrant class of acceptors . Chem. Rev. , 103 : 2305 – 2077 . Review:
  • Hartke , K. and Gunther , O. 1973 . Thion‐ und Dithioester, XI: Kondensation von Acetonitril mit Thiocarbonsre‐O‐estern und Dithiocarbondreestern . Justus Liebigs Ann. Chem. , : 1637 – 1643 .
  • Bhattacharjee , S. S. , Ila , H. and Junjappa , H. 1982 . Cyanotrimethylammonium methylid, formation and reaction with α,β‐unsaturated carbonyl compounds: Novel cyclopropanation with an ammonium ylid . Synthesis , 4 : 301 – 302 .
  • Kendall , J. D. and Edwards , H. D. U.S. Patent 2,493,071 . (1950) . Chem. Abstr. 1950 44 7347
  • Zhang , S. , Liu , Q. , Zhu , Z. , Zhang , C. and Huang , H. 1994 . Studies on the basic assisted decomposition of α,α‐dioxo(ester) ketene dithioacetals . Chem. J. Chin. Univ. , 15 : 1155 – 1158 .
  • Fang , Q. , Liu , Q. , Hu , Y. and Lin , C. 1995 . A new method for the synthesis of α‐aroyl ketene dithioacetals . Chem. J. Chin. Univ. , 16 : 1896 – 1898 .
  • Ouyang , Y. , Dong , D. , Yu , H. , Liang , Y. and Liu , Q. 2006 . A clean facile and practical synthesis of α‐oxoketene S,S‐acetals in water . Adv. Synth. Catal. , 348 : 206 – 210 .
  • Zhao , L. , Liang , F. , Bi , X. , Sun , S. and Liu , Q. 2006 . Efficient synthesis of highly functionalized dihydropyrido[2,3‐d]pyrmidines by a double annulation strategy from α‐alkenoyl‐α‐carbamoyl ketene‐(S,S)‐acetals . J. Org. Chem. , 71 : 1094 – 1098 .
  • Anabha , E. R. and Asokan , C. V. 2006 . A Convenient preparation of 2‐aroyl‐3,3‐bis(alkylsulfanyl)acrylaldehydes and their application in the synthesis of 5‐aroyl‐2‐oxo‐1,2‐dihydro‐2‐pyrdinecarbonitriles . Synthesis , 1 : 151 – 155 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.