One step synthesis of imidazole and benzimidazole acycloaromatic nucleoside analogs

A facile and rapid method for the synthesis of novel imidazole and benzimidazole aromatic acyclic nucleosides is described. Synchronous N-alkylation of imidazole or benzimidazole and potassium aryloxide with methylene iodide in the presence of triethylamine and a catalytic amount of tetrabutylammoni...

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Published inTetrahedron Vol. 58; no. 52; pp. 10341 - 10344
Main Authors Khalafi-Nezhad, A, Rad, MNS, Hakimelahi, GH, Mokhtari, B
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 23.12.2002
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
DESIGN
acycloaromatic nucleosides
POTENTIAL AGENTS
imidazole
benzimidazole
HUMAN CYTOMEGALOVIRUS INFECTIONS
ANTIVIRAL EVALUATION
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Abstract A facile and rapid method for the synthesis of novel imidazole and benzimidazole aromatic acyclic nucleosides is described. Synchronous N-alkylation of imidazole or benzimidazole and potassium aryloxide with methylene iodide in the presence of triethylamine and a catalytic amount of tetrabutylammonium bromide (TBAB) in dry acetonitrile or acetone gave moderate yields of the acycloaromatic nucleoside analogs. (C) 2002 Elsevier Science Ltd. All rights reserved.
AbstractList A facile and rapid method for the synthesis of novel imidazole and benzimidazole aromatic acyclic nucleosides is described. Synchronous N-alkylation of imidazole or benzimidazole and potassium aryloxide with methylene iodide in the presence of triethylamine and a catalytic amount of tetrabutylammonium bromide (TBAB) in dry acetonitrile or acetone gave moderate yields of the acycloaromatic nucleoside analogs. (C) 2002 Elsevier Science Ltd. All rights reserved.
ArticleNumber 0040
Author Hakimelahi, GH
Rad, MNS
Mokhtari, B
Khalafi-Nezhad, A
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Cites_doi 10.1021/jm9604888
10.1021/jm00317a030
10.1021/jm960533b
10.1080/00397919308012596
10.1021/jm960462g
10.1021/ja00788a033
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Issue 52
Keywords DESIGN
acycloaromatic nucleosides
POTENTIAL AGENTS
imidazole
benzimidazole
HUMAN CYTOMEGALOVIRUS INFECTIONS
ANTIVIRAL EVALUATION
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References Zou, RM (WOS:A1997WK72600021) 1997; 40
Zou, RM (WOS:A1997WK72600020) 1997; 40
DOU HSM (WOS:000179827300010.5) 1973
ZHENZHONG L (WOS:000179827300010.11) 1993; 23
BUTLER, K (WOS:A19679859400031) 1967; 10
AMIRGHOFRAN Z (WOS:000179827300010.1) 2001; 26
KHALAFINEZHAD A (WOS:000179827300010.7) 2000; 4
MATTHEWS, HR (WOS:A1973P261900033) 1973; 95
COSAR, C (WOS:A1959WV45000013) 1959; 96
VOGEL AI (WOS:000179827300010.10) 1954
Gudmundsson, KS (WOS:A1997WK72600018) 1997; 40
DECLERCQ E (WOS:000179827300010.4) 1993; 1
NORD CE (WOS:000179827300010.9) 1982; 10
Gudmundsson (10.1016/S0040-4020(02)01415-1_BIB3) 1997; 40
De Clercq (10.1016/S0040-4020(02)01415-1_BIB6) 1993; Vol. 1
Cosar (10.1016/S0040-4020(02)01415-1_BIB1) 1959; 96
Zou (10.1016/S0040-4020(02)01415-1_BIB4) 1997; 40
Dou (10.1016/S0040-4020(02)01415-1_BIB9) 1973
Nord (10.1016/S0040-4020(02)01415-1_BIB2) 1982; 10
Zhen-Zhong (10.1016/S0040-4020(02)01415-1_BIB12) 1993; 23
Vogel (10.1016/S0040-4020(02)01415-1_BIB13) 1954
Zou (10.1016/S0040-4020(02)01415-1_BIB5) 1997; 40
Butler (10.1016/S0040-4020(02)01415-1_BIB11) 1967; 10
10.1016/S0040-4020(02)01415-1_BIB7
Amirghofran (10.1016/S0040-4020(02)01415-1_BIB8) 2001; 26
Randall Matthews (10.1016/S0040-4020(02)01415-1_BIB10) 1973; 95
References_xml – start-page: 1861
  year: 1973
  ident: WOS:000179827300010.5
  publication-title: B SOC CHIM FR
  contributor:
    fullname: DOU HSM
– volume: 26
  start-page: 16
  year: 2001
  ident: WOS:000179827300010.1
  publication-title: IRANIAN J MED SCI
  contributor:
    fullname: AMIRGHOFRAN Z
– volume: 40
  start-page: 802
  year: 1997
  ident: WOS:A1997WK72600020
  article-title: Design, synthesis, and antiviral evaluation of 2-substituted 4,5-dichloro- and 4,6-dichloro-1-beta-D-ribofuranosylbenzimidazoles as potential agents for human cytomegalovirus infections
  publication-title: JOURNAL OF MEDICINAL CHEMISTRY
  contributor:
    fullname: Zou, RM
– volume: 96
  start-page: 238
  year: 1959
  ident: WOS:A1959WV45000013
  article-title: ACTIVITY OF (HYDROXY-2' ETHYL)-1 METHYL-2 NITRO-5 IMIDAZOLE (8823 RP) IN EXPERIMENTAL TRICHOMONAS-VAGINALIS INFECTIONS
  publication-title: ANNALES DE L INSTITUT PASTEUR
  contributor:
    fullname: COSAR, C
– volume: 95
  start-page: 2297
  year: 1973
  ident: WOS:A1973P261900033
  article-title: DIFFERENTIATION OF 1,4-DISUBSTITUTED AND 1,5-DISUBSTITUTED IMIDAZOLES
  publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
  contributor:
    fullname: MATTHEWS, HR
– volume: 4
  start-page: 147
  year: 2000
  ident: WOS:000179827300010.7
  publication-title: IRANIAN BIOMEDICAL J
  contributor:
    fullname: KHALAFINEZHAD A
– volume: 10
  start-page: 891
  year: 1967
  ident: WOS:A19679859400031
  article-title: NITROIMIDAZOLE DERIVATIVES . RELATIONSHIP BETWEEN STRUCTURE AND ANTITRICHOMONAL ACTIVITY
  publication-title: JOURNAL OF MEDICINAL CHEMISTRY
  contributor:
    fullname: BUTLER, K
– volume: 10
  year: 1982
  ident: WOS:000179827300010.9
  publication-title: J ANTIMICROB CH SA35
  contributor:
    fullname: NORD CE
– volume: 40
  start-page: 785
  year: 1997
  ident: WOS:A1997WK72600018
  article-title: Synthesis and antiviral activity of certain 5'-modified analogs of 2,5,6-trichloro-1-(beta-D-ribofuranosyl)benzimidazole
  publication-title: JOURNAL OF MEDICINAL CHEMISTRY
  contributor:
    fullname: Gudmundsson, KS
– volume: 23
  start-page: 2611
  year: 1993
  ident: WOS:000179827300010.11
  publication-title: SYNTHETIC COMMUN
  contributor:
    fullname: ZHENZHONG L
– start-page: 161
  year: 1954
  ident: WOS:000179827300010.10
  publication-title: PRACTICAL ORGANIC CH
  contributor:
    fullname: VOGEL AI
– volume: 1
  start-page: 39
  year: 1993
  ident: WOS:000179827300010.4
  publication-title: ADV ANTIVIRAL DRUG D
  contributor:
    fullname: DECLERCQ E
– volume: 40
  start-page: 811
  year: 1997
  ident: WOS:A1997WK72600021
  article-title: Design, synthesis, and antiviral evaluation of 2-chloro-5,6-dihalo-1-beta-D-ribofuranosylbenzimidazoles as potential agents for human cytomegalovirus infections
  publication-title: JOURNAL OF MEDICINAL CHEMISTRY
  contributor:
    fullname: Zou, RM
– volume: 40
  start-page: 785
  year: 1997
  ident: 10.1016/S0040-4020(02)01415-1_BIB3
  publication-title: J. Med. Chem.
  doi: 10.1021/jm9604888
  contributor:
    fullname: Gudmundsson
– ident: 10.1016/S0040-4020(02)01415-1_BIB7
– volume: 10
  issue: suppl. A35
  year: 1982
  ident: 10.1016/S0040-4020(02)01415-1_BIB2
  publication-title: J. Antimicrob. Chemother.
  contributor:
    fullname: Nord
– volume: 10
  start-page: 891
  year: 1967
  ident: 10.1016/S0040-4020(02)01415-1_BIB11
  publication-title: J. Med. Chem.
  doi: 10.1021/jm00317a030
  contributor:
    fullname: Butler
– volume: 40
  start-page: 802
  year: 1997
  ident: 10.1016/S0040-4020(02)01415-1_BIB4
  publication-title: J. Med. Chem.
  doi: 10.1021/jm960533b
  contributor:
    fullname: Zou
– start-page: 1861
  year: 1973
  ident: 10.1016/S0040-4020(02)01415-1_BIB9
  publication-title: Bull. Soc. Chim. Fr.
  contributor:
    fullname: Dou
– volume: 96
  start-page: 238
  year: 1959
  ident: 10.1016/S0040-4020(02)01415-1_BIB1
  publication-title: Ann. Inst. Pasteur (Paris)
  contributor:
    fullname: Cosar
– volume: Vol. 1
  start-page: 39
  year: 1993
  ident: 10.1016/S0040-4020(02)01415-1_BIB6
  contributor:
    fullname: De Clercq
– volume: 23
  start-page: 2611
  year: 1993
  ident: 10.1016/S0040-4020(02)01415-1_BIB12
  publication-title: Synth. Commun.
  doi: 10.1080/00397919308012596
  contributor:
    fullname: Zhen-Zhong
– volume: 26
  start-page: 16
  year: 2001
  ident: 10.1016/S0040-4020(02)01415-1_BIB8
  publication-title: Iranian J. Med. Sci.
  contributor:
    fullname: Amirghofran
– year: 1954
  ident: 10.1016/S0040-4020(02)01415-1_BIB13
  contributor:
    fullname: Vogel
– volume: 40
  start-page: 811
  year: 1997
  ident: 10.1016/S0040-4020(02)01415-1_BIB5
  publication-title: J. Med. Chem.
  doi: 10.1021/jm960462g
  contributor:
    fullname: Zou
– volume: 95
  start-page: 2297
  year: 1973
  ident: 10.1016/S0040-4020(02)01415-1_BIB10
  publication-title: J. Am. Chem. Soc.
  doi: 10.1021/ja00788a033
  contributor:
    fullname: Randall Matthews
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Snippet A facile and rapid method for the synthesis of novel imidazole and benzimidazole aromatic acyclic nucleosides is described. Synchronous N-alkylation of...
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Chemistry, Organic
Physical Sciences
Science & Technology
Title One step synthesis of imidazole and benzimidazole acycloaromatic nucleoside analogs
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