A convenient, highly selective and eco-friendly N-Boc protection of pyrimidines under microwave irradiation

被引:10
作者
Bessieres, Maxime [1 ]
Roy, Vincent [1 ]
Agrofoglio, Luigi A. [1 ]
机构
[1] Univ Orleans, ICOA, UMR CNRS 7311, Orleans, France
关键词
EFFICIENT SYNTHESIS; TERT-BUTYLOXYCARBONYLATION; ACID; SOLVENT;
D O I
10.1039/c4ra13033b
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Protected pyrimidine nucleobases are of major importance as intermediates in the synthesis of nucleoside analogues and molecules with biological interests. We describe herein a novel practical microwave-assisted N-Boc protection of pyrimidine nucleobases under mild conditions using silica gel, avoiding treatment steps, and in increased yield.
引用
收藏
页码:59747 / 59749
页数:3
相关论文
共 25 条
[11]   NUCLEIC-ACID COMPONENTS AND THEIR ANALOGS .153. PREPARATION OF 2'-DEOXY-L-RIBONUCLEOSIDES OF PYRIMIDINE SERIES [J].
HOLY, A .
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1972, 37 (12) :4072-4087
[12]  
Hwu JR, 1996, TETRAHEDRON LETT, V37, P2035
[13]   Efficient N-arylation and N-alkenylation of the five DNA/RNA nucleobases [J].
Jacobsen, Mikkel F. ;
Knudsen, Martin M. ;
Gothelf, Kurt V. .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (24) :9183-9190
[14]   Recent advances in antimicrobial nucleoside antibiotics targeting cell wall biosynthesis [J].
Kimura, K ;
Bugg, TDH .
NATURAL PRODUCT REPORTS, 2003, 20 (02) :252-273
[15]   Pyrimidine as constituent of natural biologically active compounds [J].
Lagoja, IM .
CHEMISTRY & BIODIVERSITY, 2005, 2 (01) :1-50
[16]  
Li T. S., 2010, J CHIN PHARM SCI, V19, P436
[17]   Efficient synthesis of β2-amino acid by homologation of α-amino acids involving the Reformatsky reaction and Mannich-type imminium electrophile [J].
Moumne, R ;
Lavielle, S ;
Karoyan, P .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (08) :3332-3334
[18]   2-naphthalenesulfonyl as a tosyl substitute for protection of amino functions. Cyclic voltammetry studies on model sulfonamides and their preparative cleavage by reduction [J].
Nyasse, B ;
Grehn, L ;
Maia, HLS ;
Monteiro, LS ;
Ragnarsson, U .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (19) :7135-7139
[19]   A Practical and Efficient Approach to PNA Monomers Compatible with Fmoc-Mediated Solid-Phase Synthesis Protocols [J].
Porcheddu, Andrea ;
Giacomelli, Giampaolo ;
Piredda, Ivana ;
Carta, Mariolino ;
Nieddu, Giammario .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (34) :5786-5797
[20]   Lewis acid and hexamethyldisilazane-promoted efficient synthesis of N-alkyl- and N-arylimide derivatives [J].
Reddy, PY ;
Kondo, S ;
Toru, T ;
Ueno, Y .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (08) :2652-2654