Intramolecular Aromatic Nucleophilic Substitution of the Benzimidazole-Activated Nitro Group

Organic Letters

Volumn 5, Issue 25, 2003, Pages 4795-4798

  Fekner, Tomasz ^a   Gallucci, Judith ^a   Chan, Michael K ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARGON; AROMATIC COMPOUND; BASE; BENZIMIDAZOLE DERIVATIVE; FUNCTIONAL GROUP; NITRITE; NITRO DERIVATIVE; OXIDE; SODIUM DERIVATIVE;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; HIGH TEMPERATURE; ISOMERIZATION; METHODOLOGY;

BENZIMIDAZOLES; CYCLIZATION; HETEROCYCLIC COMPOUNDS WITH 4 OR MORE RINGS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; NITRO COMPOUNDS;

EID: 0347052794     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035761w     Document Type: Article

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28. 2O-exchangeable primary and secondary hydroxyl groups, respectively, gave the anticipated splitting patterns. In addition, the aromatic proton located ortho to the aryl-heteroaryl axis in the seven-membered cyclic ether 25 experiences a far greater downfield shift than the analogous proton in the rotationally less restricted eight-membered cyclic ether 26 (8.44 and 7.74 ppm, respectively). The identity of the hydroxymethyl compound 25 was further confirmed by its conversion, via the corresponding tosylate, into its methyl analogue 27.
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