Novel Generation of Pyridinium Ylides from N-(Silylmethyl)pyridone Analogs via 1,4-Silatropy and their 1,3-Dipolar Cycloadditions Leading to N-Heteropolycycles

Abstract

Non-stabilized pyridinium methylides were successfully generated from N-(siliymethyl)pyridone analogs via 1,4-silatropy and the resulting 1,3-dipoles were trapped by reaction with acetylenic and olefinic dipolarophiles to afford N-heteropolycycles. The method does not require the use of any additives or strong bases.

Key words

1,3-dipolar cycloaddition - 1,4-silatropy - pyridinium methylides - pyridone analogs - N-heterocycles

References

• 1 Huisgen R. In 1,3-Dipolar Cycloaddition Chemistry   Vol. 1:  Padwa A. Wiley; New York: 1984. 
• For reviews, see:
• 2a Lown JW. In 1,3-Dipolar Cycloaddition Chemistry   Vol.1:  Padwa A. Wiley; New York: 1984.  p.653 
• 2b Vedejs E. West FG. Chem. Rev.  1986,  86:  941 
• 2c Tsuge O. Kanemasa S. Adv. Heterocycl. Chem.  1989,  45:  231 
• 3 Ohno M. Komatsu M. Miyata H. Ohshiro Y. Tetrahedron Lett.  1991,  32:  5813 
• 4a Uchida T. Matsumoto K. Synthesis  1976,  209 
• 4b Swinbourne FJ. Hunt JH. Klinkert G. Adv. Heterocycl. Chem.  1978,  23:  103 
• 5 Kröhnke F. Angew. Chem.  1953,  65:  605 
• 6 Ratts KW. Howe RK. Phillips WG. J. Am. Chem. Soc.  1963,  91:  6115 
• 7a Tsuge O. Kanemasa S. Kuraoka S. Takenaka S. Chem. Lett.  1984,  279 
• 7b Miki Y. Hachiken H. Takemura S. Heterocycles  1984,  22:  701 
• 8 Sliwa W. Heterocycles  1984,  22:  705 
• 9 Matsuda Y. Kohra S. Katou K. Itou T. Uemura T. Heterocycles  1997,  45:  2223 
• 10 Potts KT. Yao S. J. Org. Chem.  1979,  44:  977 
• 11 McEwen WE. Mineo IC. Shen YH. J. Am. Chem. Soc.  1971,  93:  4479 
• 12 Potts KT. Borbeaux KG. Kuehuling WR. Salsbury RL. J. Org. Chem.  1985,  50:  1677 
• 13 Meth-Cohn O. Tetrahedron Lett.  1975,  413