51549-18-9Relevant academic research and scientific papers
CuI controlled C-C and C-N bond formation of heteroaromatics through C(sp3)-H activation
Xia, Ran,Niu, Hong-Ying,Qu, Gui-Rong,Guo, Hai-Ming
supporting information, p. 5546 - 5549 (2013/01/15)
A new method for C-C and C-N bond formation of heteroaromatics and C(sp3)-H alkanes was developed with high regioselectivity. The reaction occurred on C8 to give 8-cylcoakylpurines by C-C bond formation only promoted by tBuOOtBu, while it occurred on the amino group to give N6-alkylated purines by C-N bond formation when 2 equiv of CuI were added. A reaction mechanism was also proposed based on our preliminary experimental data.
The scope and mechanism of phosphonium-mediated SNAr reactions in heterocyclic amides and ureas
Wan, Zhao-Kui,Wacharasindhu, Sumrit,Levins, Christopher G.,Lin, Melissa,Tabei, Keiko,Mansour, Tarek S.
, p. 10194 - 10210 (2008/04/12)
(Chemical Equation Presented) An efficient "one-step" synthesis of cyclic amidines and guanidines has been developed. Treatment of cyclic amides and ureas with benzotriazol-l-yloxytris(dimethylamino)phosphonium hexafluorophosphate (BOP), base, and nitrogen nucleophiles leads to the formation of the corresponding cyclic amidines and guanidines, typically in good to excellent yields. This method has also been used to prepare heteroaryl ethers and thioethers using phenol and thiophenol nucleophiles. Time course NMR and HPLC-MS studies have facilitated explicit characterization of the proposed intermediates (the phosphonium salt and HOBt adduct); the data reveal a stepwise reaction pathway.
A novel nucleophilic approach to 1-alkyladenosines. A two-step synthesis of [1-15N]adenosine from inosine
Terrazas, Montserrat,Ariza, Xavier,Farras, Jaume,Vilarrasa, Jaume
, p. 3968 - 3970 (2007/10/03)
A novel ANRORC mechanism in the reaction of 1-(2,4-dinitrobenzenesulfonyl) inosines with amines has allowed the preparation of 1-alkyladenosines and [1-15N]adenosines in a straightforward way from inosines. The Royal Society of Chemistry 2005.
A highly facile and efficient one-step synthesis of N6-adenosine and N6-2′-deoxyadenosine derivatives
Wan, Zhao-Kui,Binnun, Eva,Wilson, Douglas P.,Lee, Jinbo
, p. 5877 - 5880 (2007/10/03)
(Chemical Equation Presented) A highly facile and efficient one-step synthesis of N6-adenosine and N6-2′-deoxyadenosine derivatives has been developed. Treatment of inosine or 2′-deoxyinosine, without protection of sugar hydroxyl groups, with alkyl or arylamines, in the presence of BOP and DIPEA in DMF, led to the formation of N6- adenosine and N6-2′-deoxyadenosine derivatives in good to excellent yields. Carcinogenic polyaromatic hydrocarbon (PAH) N 6-2′-deoxyadenosine adduct 10 and a rare DNA constituent 11 were thus synthesized directly from 2′-deoxyinosine both in 98% yield.
One-pot synthesis of nucleosides using bismuth (III) bromide as catalyst
Winum, Jean-Yves,Kamal, Mehrnaz,Barragan, Veronique,Leydet, Alain,Montero, Jean-Louis
, p. 603 - 606 (2007/10/03)
A peracetylated α-D-ribofuranosyl bromide reacted with silylated heterocyclic bases in the presence of bismuth (III) bromide (a non-toxic catalyst) in a one-pot procedure to give the corresponding β-D-nucleoside in good yield.
PERMANGANATE OXIDATION OF N6,N6,8-TRISUBSTITUTED-2',3',5'-TRI-O-ACETYLADENOSINES
Kato, Tetsuo,Ogawa, Shuichi,Ito, Isoo
, p. 3205 - 3208 (2007/10/02)
Oxidation of 2',3',5'-tri-O-acetyl derivatives of N6,N6-dialkyl-adenosines(3a-g) with KMnO4 in 50percent AcOH gave both the mono(5a-g) and didealkylderivati3es(6a-c) ; it was conclusiveoly proved that one and two methylene groups of the title nucleosides(3a-g) in the α position to the exocyclic nitrogen atom were simultaneously oxidized.
