Cerium(IV)-mediated halogenation at C-5 of uracil derivatives

Asakura, Jun-Ichi; Robins, Morris J.

doi:10.1021/jo00303a033

Cited by 141 publications

(89 citation statements)

References 5 publications

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“…34 Subsequent reaction of the crude intermediate with POCl 3 and 1,2,4-triazole 33 afforded the deoxycytidine analog 10 (Scheme 3) in 51% overall based on 9, after chromatographic purification. With intermediate 10 in hand, substitution at C4 with 2-bromoaniline was performed in wet dioxane.…”

Section: Chemistrymentioning

confidence: 99%

Synthesis and spectral characterization of environmentally responsive fluorescent deoxycytidine analogs

Elmehriki

Suchý

Chicas

et al. 2014

Artificial DNA: PNA & XNA

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Section: Chemistrymentioning

confidence: 99%

Synthesis and spectral characterization of environmentally responsive fluorescent deoxycytidine analogs

Elmehriki

Suchý

Chicas

et al. 2014

Artificial DNA: PNA & XNA

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“…The synthesis of nucleoside 1a was already reported [23]. The nucleosides 1b -d were synthesized from 5-iodo-2'-deoxyuridine (3) [30] by the Sonogashira cross-coupling reaction [31] (Scheme 1). The reaction was performed in dry DMF in the presence of Et 3 N, of [Pd 0 (PPh 3 ) 4 ] and CuI as catalyst in a 1 : 2 ratio, and of an excess of the diyne or alkyne.…”

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confidence: 99%

Nucleosides and Oligonucleotides with Diynyl Side Chains: Base Pairing and Functionalization of 2′‐Deoxyuridine Derivatives by the Copper(I)‐Catalyzed AlkyneAzide ‘Click’ Cycloaddition

Seela

Sirivolu

2007

Helvetica Chimica Acta

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Oligonucleotides containing the 5‐substituted 2′‐deoxyuridines 1b or 1d bearing side chains with terminal CC bonds are described, and their duplex stability is compared with oligonucleotides containing the 5‐alkynyl compounds 1a or 1c with only one nonterminal CC bond in the side chain. For this, 5‐iodo‐2′‐deoxyuridine (3) and diynes or alkynes were employed as starting materials in the Sonogashira cross‐coupling reaction (Scheme 1). Phosphoramidites 2b–d were prepared (Scheme 3) and used as building blocks in solid‐phase synthesis. Tm Measurements demonstrated that DNA duplexes containing the octa‐1,7‐diynyl side chain or a diprop‐2‐ynyl ether residue, i.e., containing 1b or 1d, are more stable than those containing only one triple bond, i.e., 1a or 1c (Table 3). The diyne‐modified nucleosides were employed in further functionalization reactions by using the protocol of the CuI‐catalyzed Huisgen–Meldal–Sharpless [2+3] cycloaddition (‘click chemistry’) (Scheme 2). An aliphatic azide, i. e., 3′‐azido‐3′‐deoxythymidine (AZT; 4), as well as the aromatic azido compound 5 were linked to the terminal alkyne group resulting in 1H‐1,2,3‐triazole‐modified derivatives 6 and 7, respectively (Scheme 2), of which 6 forms a stable duplex DNA (Table 3). The Husigen–Meldal–Sharpless cycloaddition was also performed with oligonucleotides (Schemes 4 and 5).

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“…21 The presence of this iminic group is also contion. The NMR spectra were obtained from solu- Figure 2, analogously to the 15 N chemical shifts observed for N 3 of Urd tively, thus confirming the presence in the same solution of the dicarbonylic form I.…”

Section: Methodsmentioning

confidence: 96%

An NMR and vibrational study of 5-bromouridine and its base pairing with guanosine and adenosine

Morelli¹,

Tinti²,

Tosi³

et al. 1997

Biospectroscopy

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Cerium(IV)-mediated halogenation at C-5 of uracil derivatives

Cited by 141 publications

References 5 publications

Synthesis and spectral characterization of environmentally responsive fluorescent deoxycytidine analogs

Synthesis and spectral characterization of environmentally responsive fluorescent deoxycytidine analogs

Nucleosides and Oligonucleotides with Diynyl Side Chains: Base Pairing and Functionalization of 2′‐Deoxyuridine Derivatives by the Copper(I)‐Catalyzed AlkyneAzide ‘Click’ Cycloaddition

An NMR and vibrational study of 5-bromouridine and its base pairing with guanosine and adenosine

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