Microwave promoted reaction of purin-6-yl magnesium halides with aldehydes in dichloromethane at 100 °C

被引:6
作者
Gordon, Malcolm R. [1 ]
Lindell, Stephen D. [1 ]
机构
[1] Bayer AG, Crop Sci Div, Ind Pk Hochst, Frankfurt, Germany
关键词
Purin-6-yl magnesium halide; Microwave; Dichloromethane; Nucleobase; Grignard; NUCLEOSIDES; PURINES;
D O I
10.1016/j.tetlet.2018.04.014
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Treatment of a dichloromethane solution of 9-benzyl or 9-phenyl 6-iodopurine with ethereal ethylmagnesium bromide at ambient temperature gives the corresponding purin-6-yl magnesium halides. Addition of an aldehyde followed by heating at 100 degrees C in a microwave reactor yielded the corresponding carbinols in 52-81% yield. (C) 2018 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1945 / 1947
页数:3
相关论文
共 13 条
[1]   Synthesis, biological activity, and SAR of antimycobacterial 2-and 8-substituted 6-(2-furyl)-9-(p-methoxvbenzyl)purines [J].
Braendvang, Morten ;
Gundersen, Lise-Lotte .
BIOORGANIC & MEDICINAL CHEMISTRY, 2007, 15 (22) :7144-7165
[2]  
Burnstock G., 2012, Wiley Interdiscip. Rev. Membr. Transp. Signal., DOI DOI 10.1002/WMTS.14
[3]   An Improved Route to Purin-6-yl Magnesium Halides by Metal-Halogen Exchange in Dichloromethane [J].
Gordon, Malcolm R. ;
Lindell, Stephen D. ;
Richards, Daniel .
SYNLETT, 2018, 29 (04) :473-476
[4]   Synthesis of diverse 6-(1,2-disubstituted ethyl)purine bases and nucleosides via 6-(oxiran-2-yl)purines [J].
Kuchar, Martin ;
Pohl, Radek ;
Klepetarova, Blanka ;
Hocek, Michal .
TETRAHEDRON, 2008, 64 (45) :10355-10364
[5]   Synthesis, cytostatic, and antiviral activity of novel 6-[2-(dialkylamino)ethyl]-, 6-(2-alkoxyethyl)-, 6-[2-(alkylsulfanyl)ethyl]-, and 6-[2-(dialkylamino)vinyl]purine nucleosides [J].
Kuchar, Martin ;
Hocek, Michal ;
Pohl, Radek ;
Votruba, Ivan ;
Shih, I-hung ;
Mabery, Eric ;
Mackman, Richard .
BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (03) :1400-1424
[6]   REGIOSELECTIVE ELECTROPHILIC REACTIONS ON SUBSTITUTED PURINES - PREDOMINANT INTERMEDIACY OF 6-PURINYL OR 8-PURINYL CARBANIONS [J].
LEONARD, NJ ;
BRYANT, JD .
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (25) :4612-4616
[7]  
Miyashita A, 1998, CHEM PHARM BULL, V46, P390
[8]  
Prasad ASB, 1997, TETRAHEDRON, V53, P7237
[9]   The chemodiversity of purine as a constituent of natural products [J].
Rosemeyer, H .
CHEMISTRY & BIODIVERSITY, 2004, 1 (03) :361-401
[10]   Facile and efficient synthesis of 6-(hydroxymethyl)purines [J].
Silhár, P ;
Pohl, R ;
Votruba, I ;
Hocek, M .
ORGANIC LETTERS, 2004, 6 (19) :3225-3228