메뉴 건너뛰기




Volumn 12, Issue 19, 2010, Pages 4220-4223

Acetoacetanilides as masked isocyanates: Facile and efficient synthesis of unsymmetrically substituted ureas

Author keywords

[No Author keywords available]

Indexed keywords

ACETANILIDE DERIVATIVE; ACETOACETANILIDE; ISOCYANIC ACID DERIVATIVE; PROLINE; UREA;

EID: 77957148007     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol101474f     Document Type: Article
Times cited : (43)

References (69)
  • 1
    • 77957124765 scopus 로고    scopus 로고
    • For reviews on substituted ureas, see
    • For reviews on substituted ureas, see
  • 6
    • 77957164704 scopus 로고    scopus 로고
    • Selected examples on substituted ureas as intermediates in organic synthesis, see
    • Selected examples on substituted ureas as intermediates in organic synthesis, see
  • 12
    • 77957135420 scopus 로고    scopus 로고
    • Selected examples on urea-based bifunctional organocatalysts in organic synthesis, see
    • Selected examples on urea-based bifunctional organocatalysts in organic synthesis, see
  • 25
    • 77957148261 scopus 로고    scopus 로고
    • The reaction of isocyanates with various nucleophiles has been extensively reported in the literature, see
    • The reaction of isocyanates with various nucleophiles has been extensively reported in the literature, see
  • 27
    • 0000150949 scopus 로고
    • For the utilization of isocyanate towards the synthesis of eight-membered cyclic ureas via [6 + 2] cycloaddition, reaction with 2-vinylazetidines has been reported. See:
    • Braunstein, P.; Nobel, D. Chem. Rev. 1989, 89, 1927 For the utilization of isocyanate towards the synthesis of eight-membered cyclic ureas via [6 + 2] cycloaddition, reaction with 2-vinylazetidines has been reported. See:
    • (1989) Chem. Rev. , vol.89 , pp. 1927
    • Braunstein, P.1    Nobel, D.2
  • 28
    • 72449142146 scopus 로고    scopus 로고
    • For the reaction of isocyanatobenzene with lithiated chiral diamine towards chiral ureas, see
    • Koya, S.; Yamanoi, K.; Yamasaki, R.; Azumaya, I.; Masu, H.; Saito, S. Org. Lett. 2009, 11, 5438 For the reaction of isocyanatobenzene with lithiated chiral diamine towards chiral ureas, see:
    • (2009) Org. Lett. , vol.11 , pp. 5438
    • Koya, S.1    Yamanoi, K.2    Yamasaki, R.3    Azumaya, I.4    Masu, H.5    Saito, S.6
  • 30
    • 77957161236 scopus 로고    scopus 로고
    • For recent examples for the preparation of ureas via in situ formation of isocyanate, see
    • For recent examples for the preparation of ureas via in situ formation of isocyanate, see
  • 34
    • 77957169496 scopus 로고    scopus 로고
    • For selected representative reactions from β-ketoamides, see
    • For selected representative reactions from β-ketoamides, see
  • 45
    • 77957105378 scopus 로고    scopus 로고
    • For N -aryl urea preparation
    • For N -aryl urea preparation
  • 47
    • 77957162330 scopus 로고    scopus 로고
    • More recently, ortho -directed C-H bond activation and cross-coupling of aryl ureas have emerged. For representative examples, see
    • More recently, ortho -directed C-H bond activation and cross-coupling of aryl ureas have emerged. For representative examples, see
  • 51
    • 77957149770 scopus 로고    scopus 로고
    • Examples for the formation of isocyanates from amides under Pd catalysis, see
    • Examples for the formation of isocyanates from amides under Pd catalysis, see
  • 56
    • 77957146954 scopus 로고    scopus 로고
    • CCDC 771468 (3a) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via
    • CCDC 771468 (3a) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
  • 57
    • 77957122736 scopus 로고    scopus 로고
    • All the acetoacetanilide derivatives were either commercially available or prepared according to the procedure reported. See
    • All the acetoacetanilide derivatives were either commercially available or prepared according to the procedure reported. See
  • 60
    • 77957148260 scopus 로고    scopus 로고
    • a values of the N-H
    • a values of the N-H.
  • 61
    • 77957149395 scopus 로고    scopus 로고
    • Other amines such as ethanol amine, aminopyridine, and t -butylamine were also tried but led to complex mixtures
    • Other amines such as ethanol amine, aminopyridine, and t -butylamine were also tried but led to complex mixtures.
  • 62
    • 77957118295 scopus 로고    scopus 로고
    • Decarboxylation of α-amino acids proceeds under conditions such as in the presence of ketone catalyst in hydrocarbon solvents like xylene or tetralin. For references, see
    • Decarboxylation of α-amino acids proceeds under conditions such as in the presence of ketone catalyst in hydrocarbon solvents like xylene or tetralin. For references, see
  • 67
    • 77957142275 scopus 로고    scopus 로고
    • 2 and gaseous acetone
    • 2 and gaseous acetone.
  • 68
    • 77957153735 scopus 로고    scopus 로고
    • Obviously, the formation of the iminium ion intermediate II facilitates both the decarboxylation and the enamine elimination processes
    • Obviously, the formation of the iminium ion intermediate II facilitates both the decarboxylation and the enamine elimination processes.
  • 69
    • 77957167621 scopus 로고    scopus 로고
    • We would like to thank the reviewers for valuable comments on the manuscript
    • We would like to thank the reviewers for valuable comments on the manuscript.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.