83135-02-8Relevant articles and documents
Covalent analogues of DNA base-pairs and triplets. Part 3: Synthesis of 1,4- and 1,3-bis(purin-6-yl)benzenes and 1-(1,3-dimethyluracil-5-yl)-3 or 4-(purin-9-yl)benzenes
Havelková, Martina,Dvo?ák, Dalimil,Hocek, Michal
, p. 7431 - 7435 (2002)
The Stille cross-coupling reactions of 1,4- and 1,3-bis(trialkylstannyl)benzenes 2 or 3 with 9-benzyl-6-chloropurine (1) led either to mono-coupled 4- or 3-[(tributylstannyl)phenyl]benzenes 5a and 5b or to bis(9-benzylpurin-6-yl)benzenes (4a or 4b) depending on the ratio of the starting compounds, nature of the stannane and conditions. Analogous reaction of 1 with benzene-1,4-diboronic acid gave selectively 4a in good yield. The reaction of stannanes 5 with 1,3-dimethyl-5-iodouracil gave 1-(9-benzylpurin-6-yl)-4- or -3-(1,3-dimethyluracil-5-yl)benzenes (10a and 10b) in low yields. Compounds 4 and 10 are novel types of covalently linked analogues of nucleobase-pairs.
PdII-Catalyzed Purine-Directed Ortho Nitration of 6-Arylpurines by C(sp2)–H Activation: A Practical Approach to Synthesize 6-(2-Nitroaryl)-Purine Derivatives
Gou, Quan,Li, Wenxi,Zhao, Qingsheng,Xie, Jia,Luo, Ping,Cao, Guang,Chen, Suiyun,Qin, Jun
supporting information, p. 4089 - 4094 (2018/08/21)
Herein we report a method for PdII-catalyzed purine-directed ortho nitration of 6-arylpurines via C(sp2)–H activation by using tBuONO/O2 as nitration agent. This procedure is highly efficient and produces a range of 6-(2-nitroaryl)-purine derivatives with good chemoselectivity and functional-group tolerance. The utility of the method is further illustrated in the synthesis of antibacterial agent.
Visible-Light-Mediated Monoselective Ortho C-H Arylation of 6-Arylpurine Nucleosides with Diazonium Salts
Liang, Lei,Xie, Ming-Sheng,Wang, Hai-Xia,Niu, Hong-Ying,Qu, Gui-Rong,Guo, Hai-Ming
, p. 5966 - 5973 (2017/06/07)
A combined palladium- and photoredox-catalyzed monoselective arylation of 6-arylpurine nucleosides has been developed by employing purine as a directing group via the photoredox reaction, and many functional groups are well tolerated in this direct C-H arylation condition. Various of functionalized purines (nucleosides) which are potentially of great importance in medicinal chemistry could be obtained under visible light irradiation at room temperature within 4 h.
Silver-Catalyzed Direct C6–H Arylation of Purines and Purine Nucleosides with Arylboronic Acids
Tian, Miao,Yu, Mingwu,Shi, Tingting,Hu, Junbin,Li, Shunlai,Xu, Jiaxi,Chen, Ning,Du, Hongguang
supporting information, p. 3415 - 3420 (2017/07/05)
A practical and operationally simple protocol for the assembly of 6-aryl-substituted purines through the direct C6–H arylation of purines and 8-azapurine and purine nucleosides from arylboronic acids was developed. This reaction was performed under ambient conditions with ammonium persulfate as the oxidant in the presence of silver(I). The reaction was found to be regioselective with the arylation occurring predominantly at the C6 position, and a large variety of functional groups, including halides, esters, hydroxy groups, and heterocycles, were tolerated.
Rhodium-catalyzed intermolecular amidation of arenes with sulfonyl azides via chelation-assisted C-H bond activation
Kim, Ji Young,Park, Sae Hume,Ryu, Jaeyune,Cho, Seung Hwan,Kim, Seok Hwan,Chang, Sukbok
supporting information; scheme or table, p. 9110 - 9113 (2012/07/14)
We report the direct amidation of arene C-H bonds using sulfonyl azides as the amino source to release N2 as the single byproduct. The reaction is catalyzed by a cationic rhodium complex under external oxidant-free conditions in the atmospheric environment. A broad range of chelate group-containing arenes are selectively amidated with excellent functional group tolerance, thus opening a new avenue to practical intermolecular C-N bond formation.
Microwave promoted palladium-catalyzed Suzuki-Miyaura cross-coupling reactions of 6-chloropurines with sodium tetraarylborate in water
Qu, Gui-Rong,Xin, Peng-Yang,Niu, Hong-Ying,Jin, Xin,Guo, Xiao-Ting,Yang, Xi-Ning,Guo, Hai-Ming
experimental part, p. 9099 - 9103 (2011/12/01)
An efficient method for the synthesis of 6-arylpurines (nucleosides) was developed via Suzuki-Miyaura cross-coupling reactions of 6-chloropurines (nucleosides) and sodium tetraarylborate in neat water (ethanol). The process gave good to high isolated yiel
Cross-coupling reactions of halopurines with aryl- and alkyltrifluoroborates; the scope and limitations in the synthesis of modified purines
Hasnik, Zbynek,Pohl, Radek,Hocek, Michal
experimental part, p. 1309 - 1317 (2009/12/07)
The scope and limitations of the use of the palladium-catalyzed cross-coupling reactions of diverse alkyl- and aryltrifluoroborates with halopurines have been studied. While aryl- and hetaryltrifluoroborates reacted readily with both 6-chloropurines and 8
Reductive dimerization of 2- and 6-iodopurines: Side reaction in Pd-catalyzed cross-coupling of iodopurines
Tobrman, Tomas,Dvorak, Dalimil
, p. 1365 - 1374 (2008/09/17)
In the presence of a Pd catalyst and a base, 6- and 2-iodopurine derivatives undergo reductive C-C dimerization with the formation of the corresponding 6,6′- or 2,2′-dimers. The best results of the dimerization were obtained in the presence of i-Pr2
Isonitriles as efficient ligands in Suzuki-Miyaura reaction
Villemin, Didier,Jullien, Arnaud,Bar, Nathalie
, p. 4191 - 4193 (2008/02/05)
Isonitrile palladium complexes [(RNC)2PdCl2] were prepared and tested in Suzuki reaction of 4-chloroanisol. (AdNC)2PdCl2 was found the most effective catalyst and was used in phenylation of several chloro and bromoaromatic substrates.
Palladium-catalysed phenylation of heteroaromatics in water or methylformamide under microwave irradiation
Villemin, Didier,Gómez-Escalonilla, María José,Saint-Clair, Jean-Francois
, p. 635 - 637 (2007/10/03)
Rapid and efficient palladium-catalysed phenylation of heteroaromatic halides take place under focused microwave irradiation in water of monomethylformamide.