A simple preparation of N-vinyl derivatives of DNA nucleobases.

被引:33
作者
Ciapetti, P [1 ]
Taddei, M [1 ]
机构
[1] Univ Sassari, Dipartimento Chim, I-07100 Sassari, Italy
关键词
D O I
10.1016/S0040-4020(98)00670-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
1-Vinylpyrimidines and 9-vinylpurines have been prepared via selective alkylation of the heterocyclic ring with 1,2-dibromoethane (or 1,2-dibromopropanol) followed by dehydrobromination with sodium ethoxide in ethanol/ DME. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:11305 / 11310
页数:6
相关论文
共 11 条
[1]   SYNTHETIC SPECTROSCOPIC MODELS RELATED TO COENZYMES AND BASE PAIRS .2. EVIDENCE FOR INTRAMOLECULAR BASE-BASE INTERACTIONS IN DINUCLEOTIDE ANALOGS [J].
BROWNE, DT ;
ESINGER, J ;
LEONARD, NJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (26) :7302-&
[2]  
DULCERE JP, 1995, SYNLETT, P923
[3]  
Flyerat A., 1993, J AM CHEM SOC, V115, P9952
[4]   Synthesis of two 6-N-protected 9-N-vinyladenines as dipolarophiles in the synthesis of modified nucleosides [J].
Giglio, G ;
Napoli, A ;
Leggio, A ;
Liguori, A ;
Procopio, A ;
Siciliano, C ;
Sindona, G .
SYNTHETIC COMMUNICATIONS, 1996, 26 (22) :4211-4217
[5]   Synthesis of 4'-aza analogues of 2',3'-dideoxythymidine by 1,3-dipolar cycloadditions of nitrones to 1-N-vinyl-thymine [J].
Leggio, A ;
Liguori, A ;
Procopio, A ;
Siciliano, C ;
Sindona, G .
TETRAHEDRON LETTERS, 1996, 37 (08) :1277-1280
[6]   SYNTHESIS OF N-BOC-ALPHA-AMINO ACIDS WITH NUCLEOBASE RESIDUES AS BUILDING-BLOCKS FOR THE PREPARATION OF CHIRAL PNA (PEPTIDIC NUCLEIC-ACIDS) [J].
LENZI, A ;
REGINATO, G ;
TADDEI, M .
TETRAHEDRON LETTERS, 1995, 36 (10) :1713-1716
[7]   N-VINYL DERIVATIVES OF SUBSTITUTED PYRIMIDINES AND PURINES [J].
PITHA, J ;
TSO, POP .
JOURNAL OF ORGANIC CHEMISTRY, 1968, 33 (04) :1341-&
[8]  
Shaw G., 1984, COMPR HETEROCYCL CHE, P499
[9]   FMOC MEDIATED SYNTHESIS OF PEPTIDE NUCLEIC-ACIDS [J].
THOMSON, SA ;
JOSEY, JA ;
CADILLA, R ;
GAUL, MD ;
HASSMAN, CF ;
LUZZIO, MJ ;
PIPE, AJ ;
REED, KL ;
RICCA, DJ ;
WIETHE, RW ;
NOBLE, SA .
TETRAHEDRON, 1995, 51 (22) :6179-6194
[10]  
UEDA N, 1968, MAKROMOL CHEM, V120, P13