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Volumn 73, Issue 17, 2008, Pages 6816-6823

Divergent and regioselective synthesis of 1,2,4- and 1,2,5-trisubstituted imidazoles

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATION; CHEMICAL REACTIONS; ELECTRON TRANSITIONS; HYDROCARBONS; IODINE; ISOMERIZATION; ISOMERS; NUCLEAR MAGNETIC RESONANCE; SUGAR (SUCROSE);

EID: 51549118049     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo801256b     Document Type: Article
Times cited : (30)

References (44)
  • 1
    • 0004273844 scopus 로고    scopus 로고
    • For some reviews on imidazole synthesis, see: a, Academic Press, Inc, San Diego, CA
    • For some reviews on imidazole synthesis, see: (a) Grimmett, M. R. Imidazole and Benzimidazote Synthesis; Academic Press, Inc.: San Diego, CA, 1997.
    • (1997) Imidazole and Benzimidazote Synthesis
    • Grimmett, M.R.1
  • 2
    • 65549134628 scopus 로고    scopus 로고
    • Katritzky, A. R, Ramsden, C. A, Scriven, E. F. V, Taylor, R. J. K, Eds, Pergamon Press: Oxford
    • (b) Grimmett, M. R. In Comprehensive Heterocyclic Chemistry III; Katritzky, A. R., Ramsden, C. A., Scriven, E. F. V., Taylor, R. J. K., Eds.; Pergamon Press: Oxford, 2008; Vol. 4, pp 143-364.
    • (2008) Comprehensive Heterocyclic Chemistry III , vol.4 , pp. 143-364
    • Grimmett, M.R.1
  • 7
    • 16444367024 scopus 로고    scopus 로고
    • For reviews on biological activities of imidazoles, see: a
    • For reviews on biological activities of imidazoles, see: (a) Bolani, M.; Gonzalez, M. Mini-Rev. Med. Chem. 2005, 5, 409-424.
    • (2005) Mini-Rev. Med. Chem , vol.5 , pp. 409-424
    • Bolani, M.1    Gonzalez, M.2
  • 8
    • 33744958901 scopus 로고    scopus 로고
    • (b) Jin, Z. Nat. Prod. Rep. 2006, 23, 464-496.
    • (2006) Nat. Prod. Rep , vol.23 , pp. 464-496
    • Jin, Z.1
  • 11
    • 51549107027 scopus 로고    scopus 로고
    • For a personal example, see Supporting Information
    • For a personal example, see Supporting Information.
  • 22
    • 0041629071 scopus 로고    scopus 로고
    • For punctual examples of 1,5-substituted imidazole synthesis using a similar strategy with other protecting groups, see: a
    • For punctual examples of 1,5-substituted imidazole synthesis using a similar strategy with other protecting groups, see: (a) Chandana, P.; Nayyar, A.; Jain, R. Synth. Commun. 2003, 33, 2925-2933.
    • (2003) Synth. Commun , vol.33 , pp. 2925-2933
    • Chandana, P.1    Nayyar, A.2    Jain, R.3
  • 26
    • 51549113513 scopus 로고    scopus 로고
    • US 2005250948, 460319
    • (a) Jones, T. K.; Mani, N. US 2005250948, 2005; Chem. Abstr. 2005, 143, 460319.
    • (2005) Chem. Abstr , vol.143
    • Jones, T.K.1    Mani, N.2
  • 28
    • 33744944765 scopus 로고    scopus 로고
    • For some examples of metal-catalyzed coupling involving 4- or 5-iodoimidazoles, see: ref 1c. (a) Yang, X.; Knochel, P. Chem. Commun. 2006, 2170-2172.
    • For some examples of metal-catalyzed coupling involving 4- or 5-iodoimidazoles, see: ref 1c. (a) Yang, X.; Knochel, P. Chem. Commun. 2006, 2170-2172.
  • 37
    • 51549098095 scopus 로고    scopus 로고
    • Neither isomerization nor degradation was observed after 4 months at, 18°C
    • Neither isomerization nor degradation was observed after 4 months at - 18°C
  • 38
    • 51549112424 scopus 로고    scopus 로고
    • For both structures determined by X-ray diffraction analysis in this paper, 10 and 18, two independent molecules are observed in the asymmetric parts of the unit cell; they differ only by a slight different orientation of the phenyl group. The bond lengths indicate clearly a greater conjugation in the imidazole ring of 10 as compared to 18
    • For both structures determined by X-ray diffraction analysis in this paper, 10 and 18, two independent molecules are observed in the asymmetric parts of the unit cell; they differ only by a slight different orientation of the phenyl group. The bond lengths indicate clearly a greater conjugation in the imidazole ring of 10 as compared to 18.
  • 39
    • 51549096090 scopus 로고    scopus 로고
    • As a comparison, methylation of corresponding N-deprotected imidazole leads to a 57/43 mixture of 1,2,4- and 1,2,5-isomers (see Supporting Information).
    • As a comparison, methylation of corresponding N-deprotected imidazole leads to a 57/43 mixture of 1,2,4- and 1,2,5-isomers (see Supporting Information).
  • 41
    • 51549114792 scopus 로고    scopus 로고
    • 2 for 3 days in the presence of 0.3 equiv of the base. Conversely, formation of 13 is observed when stirring 10 in the presence of molecular sieve. (18) Once formed, the salt 14 may as well catalyze isomerization of 10.
    • 2 for 3 days in the presence of 0.3 equiv of the base. Conversely, formation of 13 is observed when stirring 10 in the presence of molecular sieve. (18) Once formed, the salt 14 may as well catalyze isomerization of 10.
  • 42
    • 51549115570 scopus 로고    scopus 로고
    • It has been noted that purity of reactants and solvent is crucial for reproducibility of this experiment (see Supporting Information, 20) The reaction was also tried under classical thermal conditions heating bath, but it was found to be much slower and leading to more side products
    • It has been noted that purity of reactants and solvent is crucial for reproducibility of this experiment (see Supporting Information). (20) The reaction was also tried under classical thermal conditions (heating bath), but it was found to be much slower and leading to more side products.
  • 44
    • 51549109450 scopus 로고    scopus 로고
    • 4 was purchased from Acros and purified prior to use following the procedure described by: Curphey, T. J. Org. Synth. 1971, 51, 142-147.
    • 4 was purchased from Acros and purified prior to use (following the procedure described by: Curphey, T. J. Org. Synth. 1971, 51, 142-147.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.