PDF herunterladen
Synlett 2011(8): 1073-1080  
DOI: 10.1055/s-0030-1260540
ACCOUNT
© Georg Thieme Verlag Stuttgart ˙ New York

[5+1]-Annulation Strategy Based on Alkenoyl Ketene Dithioacetals and Analogues

Ling Pan, Qun Liu*
Department of Chemistry, Northeast Normal University, Changchun, 130024, P. R. of China
Fax: +86(431)85099759; e-Mail: liuqun@nenu.edu.cn;
Weitere Informationen

Publikationsverlauf

Received 1 December 2010
Publikationsdatum:
20. April 2011 (online)

   Lizenzen und Reprints Alle Artikel dieser Rubrik

Abstract

Functionalized ketene dithioacetals are versatile intermediates in organic synthesis. The important multiple roles of the dialkylthio group make these substrates particularly useful for the synthesis of a number of important classes of substituted carbo- and heterocyclic systems, such as thiophenes, lactones, pyrroles, furans, pyridines, substituted cyclohexanones, and benzene derivatives. This account focuses on the utility of alkenoyl ketene dithioacetals, which have been found useful in the synthesis of six-membered carbo- and heterocyclic systems relying upon utilization of alkenoyl ketene dithioacetals, as the 1,5-bielectrophilic component in the [5+1] annulation with carbon, nitrogen, sulfur, and other nucleophiles.

1 Introduction

2 Synthesis of Alkenoyl Ketene Dithioacetals

2.1 Synthesis of α-Acetyl Ketene Dithioacetals

2.2 Synthesis of Alkenoyl Ketene Dithioacetals

3 [5C+1C] Annulation

3.1 Synthesis of Substituted Phenols, Cyclohexenones, and Hindered Benzophenones

3.2 Synthesis of Unsymmetrical Biaryls and p-Terphenyls

4 [5C+1N] Annulation

4.1 Synthesis of Functionalized 2,3-Dihydro-4-pyridones and Bipyridines

4.2 Synthesis of Substituted Pyridines

5 [5C+1S/Se] Annulation

6 Future Directions

7 Conclusions

Key words

alkenoyl ketene dithioacetals - 1,5-bielectrophiles - dialkylthio group - [5+1] annulation - carbo- and heterocyclic systems

    References

  • For reviews on acceptor-substituted ketene dithioacetals, see:
  • 1a Dieter RK. Tetrahedron  1986,  42:  3029 
    Suche in Google Scholar
  • 1b Junjappa H. Ila H. Asokan CV. Tetrahedron  1990,  46:  5423 
    Suche in Google Scholar
  • 1c Elgemeie GH. Sayed SH. Synthesis  2001,  1747 
  • For synthesis and synthetic applications of phosphonoketene dithioacetals, see:
  • 2a Minami T. Okauchi T. Matsuki H. Nakamura M. Ichikawa J. Ishida M. J. Org. Chem.  1996,  61:  8132 
    Suche in Google Scholar
  • 2b Kouno R. Okauchi T. Nakamura M. Ichikawa J. Minami T. J. Org. Chem.  1998,  63:  6239 
    Suche in Google Scholar
  • For synthesis and synthetic applications of uorinated ketene dithioacetals, see:
  • 3a Muzard M. Portella C. J. Org. Chem.  1993,  58:  29 
    Suche in Google Scholar
  • 3b Pirrung MC. Rowley EG. Holmes CP. J. Org. Chem.  1993,  58:  5683 
    Suche in Google Scholar
  • 3c Sotoca E. Bouillon J.-P. Gil S. Parra M. Portella C. Tetrahedron  2005,  61:  4395 ; and references cited therein
    Suche in Google Scholar
  • For synthesis and synthetic applications of silylketene dithioacetals, see:
  • 4a Okauchi T. Tanaka T. Minami T.
    J. Org. Chem.  2001,  66:  3924 
    Suche in Google Scholar
  • 4b Yahiro S. Shibata K. Saito T. Okauchi T. Minami T. J. Org. Chem.  2003,  68:  4947 
    Suche in Google Scholar
  • For synthesis and synthetic applications of trifluoromethylketene dithioacetals, see:
  • 5a Yoshida S. Yorimitsu H. Oshima K. Org. Lett.  2009,  11:  2185 
    Suche in Google Scholar
  • 5b Yoshida S. Yorimitsu H. Oshima K. Org. Lett.  2007,  9:  5573 
    Suche in Google Scholar
  • 5c Kobatake T. Yoshida S. Yorimitsu H. Oshima K. Angew. Chem. Int. Ed.  2010,  49:  2340 
    Suche in Google Scholar
  • 5d Kobatake T. Fujino D. Yoshida S. Yorimitsu H. Oshima K. J. Am. Chem. Soc.  2010,  132:  11838 
    Suche in Google Scholar
  • For selected recent reports, see:
  • 6a Gill S. Kocienski P. Kohler A. Pontiroli A. Liu Q. Chem. Commun.  1996,  1743 
  • 6b Peruncheralathan S. Khan TA. Ila H. Junjappa H. J. Org. Chem.  2005,  70:  10030 
    Suche in Google Scholar
  • 6c Panda K. Suresh JR. Ila H. Junjappa H. J. Org. Chem.  2003,  68:  3498 
    Suche in Google Scholar
  • 6d Liu B. Duan S. Sutterer AC. Moeller KD.
    J. Am. Chem. Soc.  2002,  124:  10101 
    Suche in Google Scholar
  • 6e Cheng D. Zhou J. Saiah E. Beaton G. Org. Lett.  2002,  4:  4411 
    Suche in Google Scholar
  • 6f Rao HSP. Sivakumar S. J. Org. Chem.  2006,  71:  8715 
    Suche in Google Scholar
  • 6g Chen L. Zhao Y. Liu Q. Cheng C. Piao C. J. Org. Chem.  2007,  72:  9259 
    Suche in Google Scholar
  • 6h Piao C. Zhao Y. Han X. Liu Q. J. Org. Chem.  2008,  73:  2264 
    Suche in Google Scholar
  • 6i Fu Z. Wang M. Ma Y. Liu Q. Liu J. J. Org. Chem.  2008,  73:  7625 
    Suche in Google Scholar
  • 6j Zhao Y. Liu Q. Zhang J. Liu Z. J. Org. Chem.  2005,  70:  6913 
    Suche in Google Scholar
  • 6k Zhao Y. Zhang W. Wang S. Liu Q. J. Org. Chem.  2007,  72:  4985 
    Suche in Google Scholar
  • 6l Wang Y. Huang J. Chai Y. Liu Q. Liang Y. Dong D. J. Comb. Chem.  2008,  10:  511 
    Suche in Google Scholar
  • 6m Savant MM. Pansuriya AM. Bhuva CV. Kapuriya N. Patel AS. Audichya VB. Pipaliya PV. Naliapara YT. J. Comb. Chem.  2010,  12:  176 
    Suche in Google Scholar
  • 6n Yuan H. Wang M. Liu Y. Wang L. Liu J. Liu Q. Chem. Eur. J.  2010,  16:  13450 
    Suche in Google Scholar
  • 6o Zhao Y. Yang S. Di C. Han X. Liu Q. Chem. Commun.  2010,  46:  7614 
    Suche in Google Scholar
  • 6p Liang D. Wang M. Bekturhun B. Xiong B. Liu Q. Adv. Synth. Catal.  2010,  352:  1593 
    Suche in Google Scholar
  • 6q Pan W. Dong D. Sun S. Liu Q. Synlett  2006,  1090 
  • 7a Joseph BK. Verghese B. Sudarsanakumar C. Deepa S. Viswam D. Chandrana P. Asokan CV. Chem. Commun.  2002,  736 
  • 7b Bi X. Liu Q. Sun S. Liu J. Pan W. Zhao L. Dong D. Synlett  2005,  49 
  • 7c Bi X. Zhang J. Liu Q. Tan J. Li B. Adv. Synth. Catal.  2007,  349:  2301 
    Suche in Google Scholar
  • 7d Li Y. Xu X. Tan J. Liao P. Zhang J. Liu Q. Org. Lett.  2010,  12:  244 
    Suche in Google Scholar
  • 7e Liu J. Wang M. Li B. Liu Q. Zhao Y. J. Org. Chem.  2007,  72:  4401 
    Suche in Google Scholar
  • 7f Zhang L. Xu X. Tan J. Xia W. Liu Q. Chem. Commun.  2010,  46:  3357 
    Suche in Google Scholar
  • 7g Ma Y. Wang M. Li D. Bekturhun B. Liu J. Liu Q. J. Org. Chem.  2009,  74:  3116 
    Suche in Google Scholar
  • 7h Liang F. Li D. Zhang L. Gao J. Liu Q. Org. Lett.  2007,  9:  4845 
    Suche in Google Scholar
  • 7i Li Y. Liang F. Bi X. Liu Q.
    J. Org. Chem.  2006,  71:  8006 
    Suche in Google Scholar
  • 7j Liang F. Zhang J. Tan J. Liu Q. Adv. Synth. Catal.  2006,  348:  1986 
    Suche in Google Scholar
  • 7k Wang M. Han F. Yuan H. Liu Q. Chem. Commun.  2010,  46:  2247 
    Suche in Google Scholar
  • 8a Ouyang Y. Dong D. Yu H. Liang Y. Liu Q. Adv. Synth. Catal.  2006,  348:  206 ; and references therein
    Suche in Google Scholar
  • 8b Wang M. Ai L. Zhang J. Liu Q. Gao L. Chin. J. Chem.  2002,  20:  1591 
    Suche in Google Scholar
  • 9 Zhang J. Zhao Y. Li D. Liang F. Liu Q. Synth. Commun.  2007,  37:  3077 
    CrossrefSuche in Google Scholar
  • 10a Wang Y. Dong D. Yang Y. Huang J. Ouyang Y. Liu Q. Tetrahedron  2007,  63:  2724 
    Suche in Google Scholar
  • 10b Wang Y. Huang J. Chai Y. Liu Q. Liang Y. Dong D. J. Comb. Chem.  2008,  10:  511 
    Suche in Google Scholar
  • 11a Choi EB. Youn IK. Pak CS. Synthesis  1991,  15 
  • 11b Liu Q. Li J. Liu J. Sun Z. Acta Chim. Sin.  2000,  53:  92 
    Suche in Google Scholar
  • 12 Ouyang Y. Dong D. Pan W. Zhang J. Liu Q. Tetrahedron  2006,  62:  10111 
    CrossrefSuche in Google Scholar
  • 13 Ai L. Liu Q. Li X. Wang M. Chem. J. Chin. Univ.  2003,  24:  1222 
    Suche in Google Scholar
  • 14 Ouyang Y. Huang J. Pan W. Liang Y. Yang Y. Dong D. Eur. J. Org. Chem.  2009,  2003 
  • 15a Silvanus AC. Groombridge BJ. Andrews BI. Kociok-Kohn G. Carbery DR. J. Org. Chem.  2010,  75:  7491 ; and references therein
    Suche in Google Scholar
  • 15b Zhang D. Xu X. Tan J. Liu Q. Synlett  2010,  917 
  • 15c Liu J. Xu X. Li D. Zhang L. Zhang K. Liu Q. Tetrahedron Lett.  2010,  51:  6918 
    Suche in Google Scholar
  • 16a Bi X. Dong D. Liu Q. Pan W. Zhao L. Li B. J. Am. Chem. Soc.  2005,  127:  4578 
    Suche in Google Scholar
  • 16b Li D. Xu X. Liu Q. Dong S. Synthesis  2008,  1895 
  • 17a Fu Z. Wang M. Dong Y. Liu J. Liu Q. J. Org. Chem.  2009,  74:  6105 
    Suche in Google Scholar
  • 17b Wang M. Fu Z. Feng H. Dong Y. Liu J. Liu Q. Chem. Commun.  2010,  46:  9061 
    Suche in Google Scholar
  • 18a For a review of applications of nitroalkanes in the synthesis of benzene derivatives, see: Ballini R. Palmieri A. Barboni L. Chem. Commun.  2008,  2975 
  • 18b Serra S. Fuganti C. Brenna E. Chem. Eur. J.  2007,  13:  6782 
    Suche in Google Scholar
  • 19 Zhang L. Liang F. Cheng X. Liu Q. J. Org. Chem.  2009,  74:  899 
    Suche in Google Scholar
  • 20 Zhang Q. Sun S. Hu J. Liu Q. Tan J. J. Org. Chem.  2009,  72:  139 
    Suche in Google Scholar
  • 21 Zhao M. Liu Q. Hu Y. Li D. Chin. Chem. Lett.  2000,  11:  283 
    Suche in Google Scholar
  • 22a Dong D. Bi X. Liu Q. Cong F. Chem. Commun.  2005,  3580 
  • 22b Zhao L. Liang F. Bi X. Sun S. Liu Q. J. Org. Chem.  2006,  71:  1094 
    Suche in Google Scholar
  • 23 Hu J. Zhang Q. Yuan H. Liu Q. J. Org. Chem.  2008,  73:  2442 
    CrossrefSuche in Google Scholar
  • For reviews, see:
  • 24a Basavaiah D. Rao AJ. Satyanarayana T. Chem. Rev.  2003,  103:  811 
    Suche in Google Scholar
  • 24b Drewes SE. Ross GHP. Tetrahedron  1988,  44:  4653 
    Suche in Google Scholar
  • 24c Kataoka T. Kinoshita H. Eur. J. Org. Chem.  2005,  45 
  • 24d Basavaiah D. Reddy BS. Badsara SS. Chem. Rev.  2010,  110:  5447 
    Suche in Google Scholar
  • 25 Bi X. Dong D. Li Y. Zhang Q. Liu Q. J. Org. Chem.  2005,  70:  10886 
    CrossrefPubMedSuche in Google Scholar
  • 26 Pan W. Dong D. Ouyang Y. Wu R. Yang Y. Liu Q. Synthesis  2007,  2115 
    Thieme Connect
  • For reviews on Nazarov reactions, see:
  • 27a Pellissier H. Tetrahedron  2005,  61:  6479 
    Suche in Google Scholar
  • 27b Frontier AJ. Collison C. Tetrahedron  2005,  61:  7577 
    Suche in Google Scholar
  • 27c Tius MA. Eur. J. Org. Chem.  2005,  2193 
  • 28 Tan J. Xu X. Zhang L. Li Y. Liu Q. Angew. Chem. Int. Ed.  2009,  48:  2868 
    CrossrefPubMedSuche in Google Scholar
  • 29 For a review on the synthetic utility of isocyanoacetate derivatives, see: Gulevich AV. Zhdanko AG. Orru RVA. Nenajdenko VG. Chem. Rev.  2010,  110:  5235 
    CrossrefSuche in Google Scholar