Iodotrimethylsilane-Mediated Cross-Aldol Condensation: A Facile Synthesis of α,α′-Bis(substituted benzylidene)cycloalkanones [1]

 

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Abstract

A facile and efficient method for the preparation of α,α′-bis(substituted benzylidene)cycloalkanones is described for the first time using iodotrimethylsilane generated in situ from chlorotrimethylsilane and sodium iodide in acetonitrile. The reaction proceeds rapidly at room temperature, giving high yields of products.

IICT Communication No. 030516.

References

• 2a Deli J. Lorand T. Szabo D. Foldesi A. Pharmazie  1984,  39:  539 
  CrossrefGoogle Scholar
• 2b Zongchao J. Quail JW. Arora KV. Dimmock RJ. Acta Cryst., Sect. C  1989,  45:  285 
  CrossrefGoogle Scholar
• 3 Raj AA. Raghunathan R. Synth. Commun.  2002,  32:  3295 
  CrossrefGoogle Scholar
• 4 Otohiko T. Kanemasa S. Ohen M. Yorozu K. Bull. Chem. Soc. Jpn.  1987,  60:  4067 
  Google Scholar
• 5 Hathaway BA. J. Chem. Educ.  1987,  64:  367 
  CrossrefGoogle Scholar
• 6 Nakano T. Migita T. Chem. Lett.  1993,  12:  2157 
  Google Scholar
• 7 Iranpoor N. Kazemi F. Tetrahedron  1998,  54:  9475 
  CrossrefGoogle Scholar
• 8 Aoyama Y. Tanaka Y. Yoshida T. Toi H. Ogoshi H. J. Organometal. Chem.  1987,  329:  251 
  CrossrefGoogle Scholar
• 9 Bao W. Zhang Y. Ying T. Synth. Commun.  1996,  26:  503 
  Google Scholar
• 10a Yadav JS. Reddy BVS. Nagaraju A. Sarma JARP. Synth. Commun.  1996,  26:  503 
  CrossrefGoogle Scholar
• 10b Wang J.-X. Kang L. Hu Y. Wei BG. Synth. Commun.  1996,  26:  503 
  CrossrefGoogle Scholar
• 10c Zheng M. Wang L. Shao J. Zhong Q. Synth. Commun.  1997,  27:  351 
  CrossrefGoogle Scholar
• 11 Irie K. Watanabe K. Bull. Chem. Soc. Jpn.  1980,  53:  1366 
  CrossrefGoogle Scholar
• 12 Zhang X. Fan X. Niu H. Wang J. Green Chem.  2003,  5:  267 
  CrossrefGoogle Scholar
• 13 Salehi P. Khodaei MM. Zolfigol MA. Keyvan A. Monatsh. Chem.  2002,  133:  1291 
  CrossrefGoogle Scholar
• 14a Sabitha G. Reddy GSKK. Reddy CS. Yadav JS. Synlett  2003,  858 
  CrossrefGoogle Scholar
• 14b Sabitha G. Reddy GSKK. Reddy CS. Yadav JS. Tetrahedron Lett.  2003,  44:  4129 
  CrossrefGoogle Scholar
• 14c Sabitha G. Yadav JS. Synth. Commun.  1998,  28:  3065 
  CrossrefGoogle Scholar
• 14d Sabitha G. Abraham S. Reddy BVS. Yadav JS. Tetrahedron Lett.  1999,  40:  1569 
  CrossrefGoogle Scholar
• 15 Yadav JS. Reddy BVS. Sadasiv K. Satheesh G. Tetrahedron Lett.  2002,  43:  9695 
  CrossrefGoogle Scholar
• 16 Nekano T. Irifune S. Vmano S. Inada A. Ishii Y. Ogawa M. J. Org. Chem.  1987,  52:  2239 
  CrossrefGoogle Scholar
• 17 Beilsteins Handbuch der Organischen Chemie   Vol. 7:  Springer; Berlin: 1925.  p.513 
  Google Scholar
• 18 Beilsteins Handbuch der Organischen Chemie   Vol. 8:  Springer; Berlin: 1925.  p.359 
  Google Scholar
• 19 Beilsteins Handbuch der Organischen Chemie   Vol. 7:  Springer; Berlin: 1925.  p.535 
  Google Scholar
• 20 Beilsteins Handbuch der Organischen Chemie   Vol. 7:  Springer; Berlin: 1925.  p.403 
  Google Scholar
• 21 Beilsteins Handbuch der Organischen Chemie   Vol. 7:  Springer; Berlin: 1925.  p.514 
  Google Scholar

IICT Communication No. 030516.