Abstract
Anionic adduct derived from malononitrile and heterocumulenes attacks on aziridines or oxiranes in regioselective manner to afford corresponding heterocycles containing highly polarized double bond. This transformation is carried out using Li2CO3 at 25–60 °C in DMF.
Graphical abstract
Similar content being viewed by others
References
Sandstrom J, Wenoerbeck I (1970) Acta Chem Scand 24:1191
Fischer G, Rudorf WD, Kleinpeter E (1991) Magn Reson Chem 29:212
Kleinpeter E, Klod S, Rudorf WD (2004) J Org Chem 69:4317
Kleinpeter E, Koch A, Heydenreich M, Chatterjee SK, Rudorf WD (1995) J Mol Struct 356:25
Forni A, Destro R (2003) Chem Eur J 9:5528
Yavari I, Ghazanfarpour-Darjani M, Solgi Y, Ahmadian S (2011) Helv Chim Acta 94:639
Benassi R, Bertarini C, Kleinpeter E, Taddei F, Thomas S (2000) J Mol Struct Theochem 498:201
Foster JP, Weinhold F (1980) J Am Chem Soc 102:7211
Fischer G, Kleinpeter E (1991) Magn Reson Chem 29:209
Kleinpeter E (1996) J Mol Struct 380:139
Marchand P, Frageau-Bellassoued MC, Bellec C, Lhommet G (1994) Synthesis 26:1118
Kleinpeter E, Schulenburg A (2005) Tetrahedron Lett 46:5995
Markovi R, Shirazi A, D`ambaski Z, Baranac M (2001) Tetrahedron 57:5833
Forni A, Destro R (2003) Chem Eur J 9:5528
Michalik M, Freier T, Reinke H (2002) J Chem Soc Perkin Trans 2 114
Michalik M, Evers R (1989) Wiss Z Univ Rostock 38:9
Samzadeh-Kermani A (2014) Monatsh Chem 145:611
Samzadeh-Kermani A (2014) Synlett 25:1839
Samzadeh-Kermani A (2015) Synlett 26:643
Ando T, Kano D, Minakata S, Ryu N, Komatsu M (1998) Tetrahedron 54:13485
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Samzadeh-Kermani, A. One-pot synthesis of heterocyclic compounds containing highly polarized double bond. Monatsh Chem 147, 761–765 (2016). https://doi.org/10.1007/s00706-015-1529-1
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00706-015-1529-1