NUCLEOSIDES .3. REACTIONS OF AICA-RIBOSIDE WITH ISOTHIOCYANATES - A CONVENIENT SYNTHESIS OF ISOGUANOSINE AND XANTHOSINE DERIVATIVES

被引：24

作者：

CHERN, JW

LIN, GS

CHEN, CS

TOWNSEND, LB

机构：

[1] UNIV MICHIGAN,COLL PHARM,DEPT MED CHEM,ANN ARBOR,MI 48109

[2] UNIV MICHIGAN,DEPT CHEM,ANN ARBOR,MI 48109

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 13期

关键词：

D O I：

10.1021/jo00013a026

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cyclodesulfurative annulations of 5-[1-(3-substituted-thioureido)]-1-(beta-D-ribofuranosyl)imidazole-4-carboxamides (3a-h) with N,N'-dicyclohexylacarbodiimide are described. Isoguanosine (4) and several 1-substituted isoguanosines 6a-f,h are readily prepared by a ring closure of the appropriate resulting 5-(3-substituted-1-ureido)-1-(beta-D-ribofuranosyl)imididazole-4-carbonitriles 5a-h. Treatment of the appropriate 1-substituted isoguanosines under basic conditions has furnished the corresponding 1-substituted xanthosine 12.

引用

收藏

页码：4213 / 4218

页数：6

相关论文

共 25 条

[1] 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

[2]

BARTLETT RT, 1980, LIFE SCI, V26, P1089

[3] 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

[4] Remarks on crotonoside. [J].

Cherbuliez, E ;

Bernhard, K .

HELVETICA CHIMICA ACTA, 1932, 15 :978-980

[5] REACTIONS OF ANTHRANILAMIDE WITH ISOCYANATES - A NEW FACILE SYNTHESIS OF 2,3-DIHYDRO-5H-OXAZOLO[2,3-B]QUINAZOLIN-5-ONE AND 3,4-DIHYDRO-2H,6H-[1,3]OXAZINO[2,3-B]QUINAZOLIN-6-ONE [J].

CHERN, JW ;

SHISH, FJ ;

CHANG, CD ;

CHAN, CH ;

LIU, KC .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1988, 25 (04) :1103-1105

[6] 2H-1,2,4-BENZOTHIADIAZINE 1,1-DIOXIDES .2. A CONDENSATION OF 2-AMINOBENZENESULFONAMIDE WITH CHLOROALKYL ISOTHIOCYANATES [J].

CHERN, JW ;

WU, YH ;

LIU, KC .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1990, 27 (05) :1485-1488

[7] AN UNEXPECTED PRODUCT FROM THE CYCLODESULFURIZATION OF 5-[1-(3-METHOXYCARBONYL)THIOUREIDO]-1-(BETA-D-RIBOFURANOSYL)IMIDAZOLE-4-CARBOXAMIDE WITH DICYCLOHEXYLCARBODIIMIDE [J].

CHERN, JW ;

GROZIAK, MP ;

TOWNSEND, LB .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1986, 23 (01) :153-154

[8]

CHERN JW, 1987, HETEROCYCLES, V26, P3193

[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]

CRAMER F, 1964, TETRAHEDRON LETT, P3201