Issue 16, 2013
From the journal:

RSC Advances

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

B. Janaki Ramulu,a   Tanmoy Chanda,a   Sushobhan Chowdhury,a   Ganesh C. Nandib  and  Maya Shankar Singh*a  

* Corresponding authors

a Department of Chemistry, Faculty of Science, Banaras Hindu University, Varanasi-221005, India
E-mail: mssinghbhu@yahoo.co.in
Fax: +91-542-2368127
Tel: +91-542-6702502

b Department of Chemistry, University of North Florida, 1 UNF Drive, Jacksonville, FL 32224, USA

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

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/C3RA40450A
Article type
Communication
Submitted
25 Jan 2013
Accepted
21 Feb 2013
First published
22 Feb 2013

RSC Adv., 2013,3, 5345-5349

Permissions

Request permissions

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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements