3-Cyano-2-azaanthracene-based "push-pull" fluorophores: A one-step preparation from 5-cyano-1, 2, 4-triazines and 2, 3-dehydronaphthalene, generated in situ. Issue 50 (14th December 2016)

• Record Type: Journal Article
• Authors: Kopchuk, Dmitry S.; Chepchugov, Nikolay V.; Taniya, Olga S.; Khasanov, Albert F.; Giri, Kousik; Kovalev, Igor S.; Santra, Sougata; Zyryanov, Grigory V.; Majee, Adinath; Rusinov, Vladimir L.; Chupakhin, Oleg N.
• Is Part Of: Tetrahedron letters. Volume 57:Issue 50(2016)
• Page Start: 5639
• Page End: 5643
• Publication Date: 2016-12-14
• Subjects: 1, 2, 4-Triazine -- 2, 3-Dehydronaphthalene -- Aza-Diels-Alder reaction -- 2-Azaanthracene-based fluorophores -- Photophysical properties; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2016.11.008
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: A one-step approach toward 3-cyano-2-azaanthracene fluorophores was reported. Only readily available reagents, simple one-step procedures, and short reaction times were used. The reaction proceeds with high regioselectivity. This procedure will open up a new routes for the synthesis of 3-cyano-2-azaanthracenes. Abstract: A facile one-step approach towards 3-cyano-2-azaanthracenes via the [4+2] cycloaddition reaction between 5-cyano-1, 2, 4-triazines and 2, 3-dehydronaphthalene, generated in situ from commercially available 3-amino-2-naphthoic acid, has been reported. The influence of the 1, 2, 4-triazine ring substituents nature on the product yield has been studied. The observed experimental results were confirmed by DFT calculations of the HOMO-LUMO energy levels of the both cycloaddends. The photophysical properties of the products have been investigated.