Trityl-directed regiospecific synthesis of 2,3-disubstituted bioimidazoles

Synthetic Communications

Volumn 33, Issue 16, 2003, Pages 2925-2933

  Chandana, Pooja ^a   Nayyar, Amit ^a   Jain, Rahul ^a  

^a NATIONAL INSTITUTE OF PHARMACEUTICAL EDUCATION AND RESEARCH NIPER   (India)

Author keywords

Bioimidazoles; Homolytic free radical reaction; Trityl

Indexed keywords

BIOIMIDAZOLE DERIVATIVE; FREE RADICAL; HISTAMINE DERIVATIVE; HISTIDINE DERIVATIVE; IMIDAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; THIN LAYER CHROMATOGRAPHY;

EID: 0041629071     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-120022183     Document Type: Article

References (18)

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15. For mechanistic details of the free-radical reaction, please see: (a) Minisci, F.; Bernardi, R.; Bertini, F.; Galli, R.; Perchinummo, M. Nucleophilic character of alkyl radical - IV. A new convenient selective alkylation of heteroaromatic bases. Tetrahedron 1971, 27, 3575-3579; (b) Minisci, F. Novel applications of free-radical reactions in preparative organic chemistry. Synthesis 1973, 1-24; (c) Minisci, F.; Vismara, E.; Fontana, F. Recent developments of free-radical substitution of heteroaromatic bases. Heterocycles 1989, 28, 489-519.
16. For mechanistic details of the free-radical reaction, please see: (a) Minisci, F.; Bernardi, R.; Bertini, F.; Galli, R.; Perchinummo, M. Nucleophilic character of alkyl radical - IV. A new convenient selective alkylation of heteroaromatic bases. Tetrahedron 1971, 27, 3575-3579; (b) Minisci, F. Novel applications of free-radical reactions in preparative organic chemistry. Synthesis 1973, 1-24; (c) Minisci, F.; Vismara, E.; Fontana, F. Recent developments of free-radical substitution of heteroaromatic bases. Heterocycles 1989, 28, 489-519.
17. For mechanistic details of the free-radical reaction, please see: (a) Minisci, F.; Bernardi, R.; Bertini, F.; Galli, R.; Perchinummo, M. Nucleophilic character of alkyl radical - IV. A new convenient selective alkylation of heteroaromatic bases. Tetrahedron 1971, 27, 3575-3579; (b) Minisci, F. Novel applications of free-radical reactions in preparative organic chemistry. Synthesis 1973, 1-24; (c) Minisci, F.; Vismara, E.; Fontana, F. Recent developments of free-radical substitution of heteroaromatic bases. Heterocycles 1989, 28, 489-519.
18. The optical purity of all ring-modified histidine analogues was assessed on HPLC using CHIRALPAK WH chiral column (ID 0.46 cm, particle size 10 μm), and results indicate presence of ≤1% of the D-enatiomer in all cases.