Synthesis 2020; 52(01): 40-50
DOI: 10.1055/s-0039-1690723
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© Georg Thieme Verlag Stuttgart · New York

Convenient Synthesis of Fluorescent Chromeno[4,3-d]pyrimidines from Electron-Deficient 3-Vinylchromones

Nikita M. Chernov
,
Organic Chemistry Department, Saint-Petersburg State Chemical Pharmaceutical University, Prof. Popov st. 14, Saint-Petersburg, 197376, Russian Federation   Email: h4o2@yandex.ru
,
Anastasia E. Potapova
,
Igor P. Yakovlev
› Author Affiliations
This work was funded by a Scholarship of the President of the Russian Federation (SP-2019).
Further Information

Publication History

Received: 04 September 2019

Accepted after revision: 01 October 2019

Publication Date:
21 October 2019 (online)

Abstract

We report an easy and powerful approach to the synthesis of novel chromeno[4,3-d]pyrimidine-5-acetic acids through ANRORC reaction of electron-deficient 3-vinylchromones and 1,3-N,N-binucleophiles. The reaction proceeds under mild conditions (EtOH, rt) and is applicable to a wide range of substrates. The described compounds show fluorescence in the violet-blue range (390–460 nm) with Stokes shift of 40–80 nm and moderate quantum yield (0.15–0.20). As the electron-withdrawing group is conserved in the form of an acetic acid fragment, these compounds may readily be functionalized or conjugated to a required substrate for (bio)analytical purposes.

Supporting Information

 
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