Regiochemistry in addition of Grignard reagents to N,N'-dibenzylated 2-purinones

被引：11
作者：
Andresen, G
Gundersen, LL
Rise, F
机构：
[1] Department of Chemistry, University of Oslo, N-0315 Oslo, P. O. Box 1033, Blindern
来源：
TETRAHEDRON | 1996年 / 52卷 / 40期
关键词：
D O I：
10.1016/0040-4020(96)00779-X
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
1,3-, 1,7-,1,9- and 3,7-dibenzylpurin-2-one form stable adducts when reacted with Grignard reagents. Reaction took place in the purine 6- or 8-position, and substantial differences in the regiochemical outcome of the reactions were found among the isomers. Several new classes of purinones are described here for the first time. The structure elucidations of the products were accomplished by HETCOR, COLOC, GA-HMQC and GA-HMBC NMR spectroscopy. Copyright (C) 1996 Elsevier Science Ltd
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页码：12979 / 12992
页数：14
相关论文
共 53 条
[1]   REGIOSELECTIVE ADDITION OF GRIGNARD-REAGENTS TO A 2-OXOPURINIUM SALT [J].
ANDRESEN, G ;
GUNDERSEN, LL ;
LUNDMARK, M ;
RISE, F ;
SUNDELL, S .
TETRAHEDRON, 1995, 51 (12) :3655-3664
[2]   A SYNTHESIS OF VITAMIN-A FROM CYCLOHEXANONE [J].
ATTENBURROW, J ;
CAMERON, AFB ;
CHAPMAN, JH ;
EVANS, RM ;
HEMS, BA ;
JANSEN, ABA ;
WALKER, T .
JOURNAL OF THE CHEMICAL SOCIETY, 1952, (MAR) :1094-1111
[3]   SYNTHESIS AND PHARMACOLOGICAL EVALUATION OF A SERIES OF ANALOGS OF 1-METHYLISOGUANOSINE [J].
BARTLETT, RT ;
COOK, AF ;
HOLMAN, MJ ;
MCCOMAS, WW ;
NOWOSWAIT, EF ;
POONIAN, MS ;
BAIRDLAMBERT, JA ;
BALDO, BA ;
MARWOOD, JF .
JOURNAL OF MEDICINAL CHEMISTRY, 1981, 24 (08) :947-954
[4]   SYNTHESIS OF 6-ALKYL AND 6-ARYL SUBSTITUTED 9-BETA-D-RIBOFURANOSYL PURINES VIA THE NICKEL CATALYZED COUPLING OF GRIGNARD-REAGENTS TO 2',3',5'-TRIS-O-(TERT-BUTYLDIMETHYLSILYL)-9-BETA-D-RIBOFURANOSYL-6-CHLOROPURINE [J].
BERGSTROM, DE ;
REDDY, PA .
TETRAHEDRON LETTERS, 1982, 23 (41) :4191-4194
[5]   LONGAMIDE AND 3,7-DIMETHYLISOGUANINE, 2 NOVEL ALKALOIDS FROM THE MARINE SPONGE AGELAS-LONGISSIMA [J].
CAFIERI, F ;
FATTORUSSO, E ;
MANGONI, A ;
TAGLIALATELASCAFATI, O .
TETRAHEDRON LETTERS, 1995, 36 (43) :7893-7896
[6]   BIOSYNTHESIS AND CYTOKININ ACTIVITY OF 8-HYDROXY AND 2,8-DIHYDROXY DERIVATIVES OF ZEATIN AND N6-(DELTA2-ISOPENTENYL)ADENINE [J].
CHEN, CM ;
SMITH, OC ;
MCCHESNEY, JD .
BIOCHEMISTRY, 1975, 14 (14) :3088-3093
[7]   Research into croton seed. I. On the crotonoside (2-oxy-6-amino-purine-d-riboside) [J].
Cherbuliez, E ;
Bernhard, K .
HELVETICA CHIMICA ACTA, 1932, 15 :464-471
[8]  
CONGDANH N, 1979, TETRAHEDRON LETT, P3159
[9]   1-METHYLISOGUANOSINE, A PHARMACOLOGICALLY ACTIVE AGENT FROM A MARINE SPONGE [J].
COOK, AF ;
BARTLETT, RT ;
GREGSON, RP ;
QUINN, RJ .
JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (20) :4020-4025
[10]   PLANT-GROWTH FACTORS PRODUCED BY THE FUNGUS ALTERNARIA-BRASSICAE [J].
DAHIYA, JS ;
TEWARI, JP .
PHYTOCHEMISTRY, 1991, 30 (09) :2825-2828
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