Issue 16, 2013

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

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.

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

Supplementary files

Article information

Article type
Communication
Submitted
25 Jan 2013
Accepted
21 Feb 2013
First published
22 Feb 2013

RSC Adv., 2013,3, 5345-5349

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

B. J. Ramulu, T. Chanda, S. Chowdhury, G. C. Nandi and M. S. Singh, RSC Adv., 2013, 3, 5345 DOI: 10.1039/C3RA40450A

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