Organocatalyzed straightforward synthesis of highly fluorescent 3,5-disubstituted 2,6-dicyanoanilines via domino annulation of α-enolicdithioesters with malononitrile

Ramulu, B. Janaki ; Chanda, Tanmoy ; Chowdhury, Sushobhan ; Nandi, Ganesh C. ; Singh, Maya Shankar (2013) Organocatalyzed straightforward synthesis of highly fluorescent 3,5-disubstituted 2,6-dicyanoanilines via domino annulation of α-enolicdithioesters with malononitrile RSC Advances, 3 (16). p. 5345. ISSN 2046-2069

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Official URL: http://doi.org/10.1039/C3RA40450A

Related URL: http://dx.doi.org/10.1039/C3RA40450A

Abstract

Piperidine mediated a robust, efficient, and selective one-pot synthesis of previously inaccessible and highly fluorescent 3,5-disubstituted 2,6-dicyanoanilines. This was achieved via the domino carboannulation of α-enolicdithioesters with malononitrile by dehydrative C[double bond, length as m-dash]O/C[double bond, length as m-dash]S bond functionalization. It is presumed that the domino sequence includes base promoted nucleophilic addition, Knoevenagel condensation and ANRORC (addition of nucleophile/ring opening/ring closure) steps. The screening for optical properties identified a strong blue emission with high fluorescence quantum yields.

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