Preparation of 8-(arylsulfanyl)adenines with diazonium salts under mild, aerobic conditions

被引：9

作者：

Biamonte, MA ^{[1
]}

Shi, JD ^{[1
]}

Hurst, D ^{[1
]}

Hong, K ^{[1
]}

Boehm, MF ^{[1
]}

Kasibhatla, SR ^{[1
]}

机构：

[1] Conforma Therapeut Corp, San Diego, CA 92121 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 02期

关键词：

D O I：

10.1021/jo048522a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

8-(Arylsulfanyl)adenines 11 were prepared in up to 75% yield by reacting the 8-thionoadenine 6 (acetic acid 3-(6-amino-8-thioxo-7,8-dihydropurin-9-yl)propyl ester) with benzenediazonium tetrafluoroborates in DMSO. Benzenediazonium ions carrying an electron-withdrawing substituent gave the highest yields. The reaction proceeded smoothly at room temperature without any base and could be performed under air atmosphere. The extremely mild conditions are compatible with a wide range of functional groups.

引用

收藏

页码：717 / 720

页数：4

相关论文

共 25 条

[1] Trifluoromethylthiodediazoniation: a simple, efficient route to trifluoromethyl aryl sulfides [J].

Adams, DJ ;

Goddard, A ;

Clark, JH ;

Macquarrie, DJ .

CHEMICAL COMMUNICATIONS, 2000, (11) :987-988

[2] THE FACILE CONVERSION OF AROMATIC-AMINES TO ARYLMETHYLSULFIDES WITH METHYLTHIOCOPPER [J].

BALEJA, JD .

SYNTHETIC COMMUNICATIONS, 1984, 14 (03) :215-218

[3] Alkyl- and arylthiodediazoniations of dry arenediazonium o-benzenedisulfonimides.: Efficient and safe modifications of the Stadler and Ziegler reactions to prepare alkyl aryl and diaryl sulfides [J].

Barbero, M ;

Degani, I ;

Diulgheroff, N ;

Dughera, S ;

Fochi, R ;

Migliaccio, M .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (18) :5600-5608

[4] On the reaction of diazonium salt with thiourea and derivatives [J].

Busch, M ;

Schulz, K .

JOURNAL FUR PRAKTISCHE CHEMIE-LEIPZIG, 1938, 150 (6/8) :173-185

[5] Development of a purine-scaffold novel class of Hsp90 binders that inhibit the proliferation of cancer cells and induce the degradation of Her2 tyrosine kinase [J].

Chiosis, G ;

Lucas, B ;

Shtil, A ;

Huezo, H ;

Rosen, N .

BIOORGANIC & MEDICINAL CHEMISTRY, 2002, 10 (11) :3555-3564

[6]

Clifford A. M., 1932, J AM CHEM SOC, V54, P1163

[7]

DRYSDALE MJ, 2003, Patent No. 03055860

[8] Inhibitors of HSP90 and other chaperones for the treatment of cancer [J].

Dymock, BW ;

Drysdale, MJ ;

McDonald, E ;

Workman, P .

EXPERT OPINION ON THERAPEUTIC PATENTS, 2004, 14 (06) :837-847

[9] General method for the synthesis of 8-arylsulfanyl adenine derivatives [J].

He, HZ ;

Llauger, L ;

Rosen, N ;

Chiosis, G .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (09) :3230-3232

[10] Researches on pyrimidines. CXIII. An improved method for the synthesis of cytosine [J].

Hilbert, GE ;

Johnson, TB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1930, 52 :1152-1157