Synthesis of nicotinonitrile derivatives as a new class of NLO materials

Abstract

4,6-Diaryl-2-(pyrrolidin-1-yl)-nicotinonitriles 2a– k and 3-amino-2,4-dicyano-5-aryl-biphenyls 3a– c were synthesized from 1,3-diaryl-prop-2-en-1-ones 1a– k and malononitrile by a convenient one-pot method. Likewise, the reaction of aromatic aldehydes with malononitrile afforded 6-amino-4-aryl-2-(pyrrolidin-1-yl)-pyridine-3,5-dicarbonitriles 6a– f . The reaction of mesityl oxide with malononitrile gave 5-amino-7-(pyrrolidin-1-yl)-2,4,4-trimethyl-1,4-dihydro-1,6-naphthyridine-8-carbonitrile 8 . The NLO studies of the pyridinedinitrile derivatives 6a, b, f showed a high value while that of nicotinonitrile 2b was weak.