Improved Synthesis of Cationic Pyridinium-Substituted Indolizines

Abstract

This paper describes the optimization of the synthesis of pyridinium-substituted indolizines. Different conditions, solution and solid-phase synthesis were used for the key step of [3+2] cycloaddition. The best yields and shortest reaction time were obtained by microwave-assisted solid-phase synthesis.

Key words

cycloadditions - fused-ring systems - heterocycles - solid-phase synthesis - ylide

References

• 1 Chai W. Breitenbucher JG. Kwok A. Li X. Wong V. Carruthers NI. Lovenberg TW. Mazur K. Wilson SJ. Axe FU. Jones TK. Bioorg. Med. Chem.  2003,  11:  1767 
• 2 Gundersen LL. Malterud KE. Negussie AH. Rise F. Teklu S. Ostby OB. Bioorg. Med. Chem.  2003,  11:  5409 
• 3 Li Y. Hu H.-Y. Ye J.-P. Fun H.-K. Hu H.-W. Xu J.-H. J. Org. Chem.  2004,  69:  2332 
• 4 Jorgensen AS. Jacobsen P. Christiansen LB. Bury PS. Kanstrup A. Thorpe SM. Naerum L. Wassermann K. Bioorg. Med. Chem. Lett.  2000,  10:  2383 
• 5 Millet R. Domarkas J. Rigo B. Goossens L. Goosens J.-F. Houssin R. Hénichart JP. Bioorg. Med. Chem.  2002,  10:  2905 
• 6 Shen Y. Zhang Y. Jiang GF. Synthesis  2002,  714 
• 7 Sonnenschein H. Hennrich G. Resch-Genger U. Schulz B. Dyes Pigm.  2000,  46:  23 
• 8 Troll T. Beckel H. Lentner-Bohm C. Tetrahedron  1997,  53:  81 
• 9 Hodgkiss RJ. Middleton RW. Parrick J. Rami HK. Wardman P. Wison GD. J. Med. Chem.  1992,  35:  1920 
• 10 Vlahovici A. Druta I. Andrei M. Cotlet M. Dinica R. J. Lumin.  1999,  82:  155 
• 11 Druta I. Dinica R. Bacu E. Humelnicu I. Tetrahedron  1998,  54:  10811 
• 12 Delattre F. Woisel P. Surpateanu G. Cazier F. Blach P. Tetrahedron  2005,  61:  3939 
• 13 Katritzky AR. Qiu G. Yang B. He H.-Y. J. Org. Chem.  1999,  64:  7618 
• 14 Brown HC. J. Org. Chem.  1985,  50:  1384 
• 15 Rheinboldt H. Perrier M. J. Am. Chem. Soc.  1947,  69:  3148 
• 16 Kröhnke F. Chem. Ber.  1935,  68B:  1177 
• 17 Dinica R. Druta I. Pettinari C. Synlett  2000,  1013