Sonogashira alkynylation of unprotected 8-brominated adenosines and guanosines: fluorescence properties of compact conjugated acetylenes containing a purine ring

TY - JOUR

T1 - Sonogashira alkynylation of unprotected 8-brominated adenosines and guanosines

T2 - fluorescence properties of compact conjugated acetylenes containing a purine ring

AU - Firth, Andrew G.

AU - Fairlamb, Ian J. S.

AU - Darley, Kate

AU - Baumann, Christoph G.

PY - 2006/5/22

Y1 - 2006/5/22

N2 - A practical Sonogashira alkynylation protocol for the preparation of 8-alkynylated adenosines and guanosines has been developed. Protection of the sugar hydroxyl substituents is not required; protection hinders the purification of these products. A preliminary fluorescent study is reported, which shows that the presence of a substituent on the phenylene ring influences the fluorescent properties considerably, an outcome that could be utilized in biological applications. (c) 2006 Elsevier Ltd. All rights reserved.

AB - A practical Sonogashira alkynylation protocol for the preparation of 8-alkynylated adenosines and guanosines has been developed. Protection of the sugar hydroxyl substituents is not required; protection hinders the purification of these products. A preliminary fluorescent study is reported, which shows that the presence of a substituent on the phenylene ring influences the fluorescent properties considerably, an outcome that could be utilized in biological applications. (c) 2006 Elsevier Ltd. All rights reserved.

KW - CROSS-COUPLING REACTION

KW - TERMINAL ALKYNES

KW - ARYL HALIDES

KW - OPTICAL-PROPERTIES

KW - NUCLEOSIDE ANALOGS

KW - SUZUKI-MIYAURA

KW - PALLADIUM

KW - COMPLEXES

KW - EFFICIENT

KW - CATALYSTS

U2 - 10.1016/j.tetlet.2006.03.100

DO - 10.1016/j.tetlet.2006.03.100

M3 - Article

SN - 0040-4039

VL - 47

SP - 3529

EP - 3533

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 21

ER -