메뉴 건너뛰기




Volumn 8, Issue 7, 2006, Pages 1291-1294

Selective magnesiation of chloro-iodopurines: An efficient approach to new purine derivatives

Author keywords

[No Author keywords available]

Indexed keywords

HALOGENATED HYDROCARBON; MAGNESIUM; PURINE DERIVATIVE;

EID: 33645951409     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol053013w     Document Type: Article
Times cited : (27)

References (35)
  • 25
    • 0000854982 scopus 로고
    • This compound was prepared by benzylation of 2-chloro-6-iodopurine, which was prepared from 2,6-dichloropurine by an exchange reaction with concentrated hydroiodic acid: Elion, G. B.; Hitchings, G. H. J. Am. Chem. Soc. 1956, 78, 3508. The position of halogens in the above paper was only estimated. Thus, the reaction described in Scheme 2 is also proof that the compound obtained from 2.6-dichloropurine by reaction with hydroiodic acid is 2-chloro-6-iodopurine and not isomeric 6-chloro-2-iodopurine.
    • (1956) J. Am. Chem. Soc. , vol.78 , pp. 3508
    • Elion, G.B.1    Hitchings, G.H.2
  • 26
    • 33645956827 scopus 로고    scopus 로고
    • note
    • The outcome of the reaction with 1 equiv of RMgCl strongly depends on the reaction temperature. Thus, the reaction with iPrMgCl at -80 °C followed with addition of water at -80 °C affords exclusively 5, whereas the same reaction at higher temperatures gives mixtures of 5 and 7a in a different ratio. Interestingly, formation of 9-benzyl-6-iodopurine or 6-isopropyl-2-chloropurine was not observed. It suggests that a Cl/Mg exchange reaction is connected with the introduction of an alkyl group to the 6 position. However, all attempts to prepare 6-alkyl-2-chloro-9-benzylpurines as putative intermediates of the formation of 9 failed.
  • 35
    • 33645918661 scopus 로고    scopus 로고
    • note
    • Preliminary results show that 2-magnesiated purines are stabilized by electron-donating substituents in the 6 position of purine nuclei.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.