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Synlett 2021; 32(17): 1714-1718
DOI: 10.1055/a-1545-7086
letter

A Convenient Approach to meso-Uracil–4,4-Difluoro-4-bora-3a, 4a-diaza-s-indacene Derivatives

M. Trapani
a   CNR- ISMN Istituto per lo Studio dei Materiali Nanostrutturati, c/o Dipartimento di Scienze Chimiche, Biologiche, Farmaceutiche e Ambientali, 98166 V. le F. Stagno D’Alcontres 31, Messina, Italy
,
M. A. Castriciano
a   CNR- ISMN Istituto per lo Studio dei Materiali Nanostrutturati, c/o Dipartimento di Scienze Chimiche, Biologiche, Farmaceutiche e Ambientali, 98166 V. le F. Stagno D’Alcontres 31, Messina, Italy
,
J. A. A. W. Elemans
b   Institute for Molecules and Materials, Radboud University, Heyendaalseweg 135, 6525 AJ, Nijmegen, the Netherlands
,
A. Nicosia
c   Dipartimento di Scienze Chimiche, University of Catania, V. A. Doria 6, 95100 Catania, Italy
,
P. Mineo
c   Dipartimento di Scienze Chimiche, University of Catania, V. A. Doria 6, 95100 Catania, Italy
d   CNR-IPCF Istituto per i Processi Chimico-Fisici, V.le F. Stagno D’Alcontres 37, I-98158 Messina, Italy
,
M. Cordaro  ∗
e   Dipartimento di Scienze Chimiche, Biologiche, Farmaceutiche e Ambientali, 98166 V. le F. Stagno D’Alcontres 31, University of Messina, Messina, Italy
› Author AffiliationsThe authors thank the MIUR (PRIN 2015 project no.2015XBZ5YA) and the MatISSE “Materiali Innovativi e Sostenibili per la Salute e l’Energia” (CUP G77B17000180009, grant to M.T.).
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Abstract

An effective and convenient protocol for the synthesis of 1-substituted uracil-6-carbaldehyde derivatives has been developed. A three-step sequence permits the preparation of uracil-6-carbaldehydes with various substituents at the N-1 in large quantities by using low-cost precursors. The aldehyde-functionalized uracils served as useful precursors for the preparation of meso-(1-substituted 6-uracil)-derivatives of 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY). In this way, regioselectively functionalized BODIPYs with a direct connection to a nucleobase were prepared in yields of 30–45%. MALDI-TOF mass spectrometry, NMR, UV/vis absorption, and steady-state and time-­resolved fluorescence spectroscopies were used to characterize the structures and the spectroscopic/photophysical properties of the resultant dyes.

Key words

difluoroboradiazaindacenes - aldehydes - dyes - atropisomerism - formyluracils

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1545-7086.
  • Supporting Information


Publication History

Received: 06 June 2021

Accepted after revision: 07 July 2021

Accepted Manuscript online:
07 July 2021

Article published online:
18 August 2021

© 2021. Thieme. All rights reserved

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