메뉴 건너뛰기




Volumn 9, Issue 2, 2007, Pages 200-203

Chemoselective reduction of nitroarenes in the presence of acid-sensitive functional groups: Solid-phase syntheses of amino aryl azides and benzotriazoles

Author keywords

[No Author keywords available]

Indexed keywords

ACID; AZIDE; BENZOTRIAZOLE; TRIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 34047222933     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc060116c     Document Type: Article
Times cited : (24)

References (24)
  • 3
    • 0036097584 scopus 로고    scopus 로고
    • For a notable heterogeneous reduction on solid supports, see
    • For a notable heterogeneous reduction on solid supports, see: Rodel, M.; Thieme, F.; Buchholz, H.; König, B. Synth. Commun. 2002, 32, 1181-1187.
    • (2002) Synth. Commun , vol.32 , pp. 1181-1187
    • Rodel, M.1    Thieme, F.2    Buchholz, H.3    König, B.4
  • 4
    • 0001722739 scopus 로고
    • For an overview of sulfide reductions, see
    • For an overview of sulfide reductions, see: Porter, H. K. Org. React. 1973, 20, 455-481.
    • (1973) Org. React , vol.20 , pp. 455-481
    • Porter, H.K.1
  • 7
    • 34047216743 scopus 로고    scopus 로고
    • Nicolaou, K. C, Hanko, R, Hartwig, W, Eds, Wiley-VCH: Weinheim, Germany
    • Corrette, C. P.; Christopher, C. W. In Handbook of Combinatorial Chemistry; Nicolaou, K. C., Hanko, R., Hartwig, W., Eds.; Wiley-VCH: Weinheim, Germany, 2002; pp 387-439.
    • (2002) Handbook of Combinatorial Chemistry , pp. 387-439
    • Corrette, C.P.1    Christopher, C.W.2
  • 13
    • 34047220742 scopus 로고    scopus 로고
    • Merrifield resin (0.93 mmol/g) was obtained from Polymer Laboratories.
    • Merrifield resin (0.93 mmol/g) was obtained from Polymer Laboratories.
  • 14
    • 0004127585 scopus 로고    scopus 로고
    • Nicolaou, K. C, Hanko, R, Hartwig, W, Eds, Wiley-VCH: Weinheim, Germany, Chapter 4
    • Dahmen, S.; Bräse, S. In Handbook of Combinatorial Chemistry; Nicolaou, K. C., Hanko, R., Hartwig, W., Eds.; Wiley-VCH: Weinheim, Germany, 2002; Chapter 4.
    • (2002) Handbook of Combinatorial Chemistry
    • Dahmen, S.1    Bräse, S.2
  • 18
    • 0034686869 scopus 로고    scopus 로고
    • 4, see: Scheuerman, R. A.; Tumelty, D. Tetrahedron Lett. 2000, 41, 6531-6535.
    • 4, see: Scheuerman, R. A.; Tumelty, D. Tetrahedron Lett. 2000, 41, 6531-6535.
  • 19
    • 34047221043 scopus 로고    scopus 로고
    • Thanks to Dr. Johannes Köbberling for suggesting this reagent
    • Thanks to Dr. Johannes Köbberling for suggesting this reagent.
  • 20
    • 2542623187 scopus 로고    scopus 로고
    • The combination of viologen with sodium sulfide was not reported earlier. During our investigation, the reduction of a nitro group with dithionite and a viologen was reported to give the aniline in a 22% yield: Carroll, W. A.; Altenbach, R. J.; Bai, H.; Brioni, J. D.; Brune, M. E.; Cassidy, C.; Chen, Y.; Coghlan, M. J.; Daza, A. V.; Drizin, I.; Fey, T. A.; Fitzgerald, M; Gopalakrishnan, M.; Turner, S. C.; Whiteaker, K. L.; Yi, L.; Zhang, H.; Sullivan, J. P, J. Med. Chem. 2004, 47, 3163-3179.
    • (a) The combination of viologen with sodium sulfide was not reported earlier. During our investigation, the reduction of a nitro group with dithionite and a viologen was reported to give the aniline in a 22% yield: Carroll, W. A.; Altenbach, R. J.; Bai, H.; Brioni, J. D.; Brune, M. E.; Cassidy, C.; Chen, Y.; Coghlan, M. J.; Daza, A. V.; Drizin, I.; Fey, T. A.; Fitzgerald, M; Gopalakrishnan, M.; Turner, S. C.; Whiteaker, K. L.; Yi, L.; Zhang, H.; Sullivan, J. P, J. Med. Chem. 2004, 47, 3163-3179.
  • 21
    • 0027432522 scopus 로고
    • For an earlier example, see also
    • (b) For an earlier example, see also: Park, K. K.; Oh, C. H.; Joung, W. K. Tetrahedron Lett. 1993, 34, 7445-7450.
    • (1993) Tetrahedron Lett , vol.34 , pp. 7445-7450
    • Park, K.K.1    Oh, C.H.2    Joung, W.K.3
  • 23
    • 0035830562 scopus 로고    scopus 로고
    • For the combination of 9 and samarium, see
    • For the combination of 9 and samarium, see: Yu, C.; Liu, B.; Hu, L. J. Org. Chem. 2001, 66, 919-924.
    • (2001) J. Org. Chem , vol.66 , pp. 919-924
    • Yu, C.1    Liu, B.2    Hu, L.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.