2-amino-6-(1,2,4-triazol-4-yl)-purine: a useful intermediate in the synthesis of 9-alkylguanines

被引:7
作者
Alarcon, K [1 ]
Martelli, A [1 ]
Demeunynck, M [1 ]
Lhomme, J [1 ]
机构
[1] Univ Grenoble 1, CNRS, UMR 5616, LEDSS, F-38041 Grenoble 9, France
关键词
guanine; 2,6-diaminopurine; 1,2,4-triazole;
D O I
10.1016/S0040-4039(00)01236-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
2-Amino-6-(1,2,4-triazol-4-yl)purine, prepared from 2,6-diaminopurine, was regioselectively alkylated at position 9. Subsequent alkaline hydrolysis afforded 9-alkylguanines in high yield. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:7211 / 7215
页数:5
相关论文
共 14 条
[1]  
ALHEDE B, 1991, J ORG CHEM, V56, P3139
[2]   TRANSAMINATIONS OF NN-DIMETHYLFORMAMIDE AZINE [J].
BARTLETT, RK ;
HUMPHREY, IR .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1967, (17) :1664-&
[3]   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-&
[4]   SYNTHESIS OF 9-SUBSTITUTED GUANINES - A REVIEW [J].
CLAUSEN, FP ;
JUHLCHRISTENSEN, J .
ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1993, 25 (04) :373-401
[5]  
Gao H, 2000, SYNTHESIS-STUTTGART, P329
[6]   TOTAL SYNTHESIS OF (-)-CARBOVIR [J].
JONES, MF ;
MYERS, PL ;
ROBERTSON, CA ;
STORER, R ;
WILLIAMSON, C .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (10) :2479-2484
[7]   Protection of 2,6-diaminopurine 2'-deoxyriboside [J].
Luyten, I ;
VanAerschot, A ;
Rozenski, J ;
Busson, R ;
Herdewijn, P .
NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 1997, 16 (7-9) :1649-1652
[8]   ALKYLPURINES AS IMMUNE POTENTIATING AGENTS - SYNTHESIS AND ANTIVIRAL ACTIVITY OF CERTAIN ALKYLGUANINES [J].
MICHAEL, MA ;
COTTAM, HB ;
SMEE, DF ;
ROBINS, RK ;
KINI, GD .
JOURNAL OF MEDICINAL CHEMISTRY, 1993, 36 (22) :3431-3436
[9]   NUCLEIC-ACID RELATED-COMPOUNDS .87. NUCLEOPHILIC FUNCTIONALIZATION OF CYTIDINE AND 2'-DEOXYCYTIDINE DERIVATIVES VIA ELABORATION OF THE 4-AMINO GROUP INTO A READILY DISPLACED 1,2,4-TRIAZOL-4-YL SUBSTITUENT [J].
MILES, RW ;
SAMANO, V ;
ROBINS, MJ .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (21) :7066-7069
[10]   NUCLEIC-ACID RELATED-COMPOUNDS .86. NUCLEOPHILIC FUNCTIONALIZATION OF ADENINE, ADENOSINE, TUBERCIDIN, AND FORMYCIN DERIVATIVES VIA ELABORATION OF THE HETEROCYCLIC AMINO GROUP INTO A READILY DISPLACED 1,2,4-TRIAZOL-4-YL SUBSTITUENT [J].
MILES, RW ;
SAMANO, V ;
ROBINS, MJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (22) :5951-5957