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Volumn 11, Issue 15, 2009, Pages 3514-3517

Reaction of thioacids with lsocyanates and lsothiocyanates: A convenient amide ligation process

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; AMINE; ISOCYANIC ACID DERIVATIVE; ISOTHIOCYANIC ACID DERIVATIVE;

EID: 68149096914     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol901370y     Document Type: Article
Times cited : (85)

References (45)
  • 10
    • 0035948251 scopus 로고    scopus 로고
    • Beyond the original paper, which itself has only been cited 14 times to date, we are only aware of four isolated examples of the reaction of isothiocyanates with simple thioacids (three with thioacetic acid and one with indolethioacetic acid) and of none between isocyanates themselves and thioacids. The four examples of isothiocyanates and thioacids all make use of heating to 60 or 80 °C to achieve the reactions described, and none of the four papers makes reference to the original work of Kricheldorf and Leppert. (a) Gonda, J.; Martinkova, M.; Walko, M.; Zavacka, E.; Budesinsky, M.; Cisarova, I. Tetrahedron Lett. 2001, 42, 4401-4404.
    • Beyond the original paper, which itself has only been cited 14 times to date, we are only aware of four isolated examples of the reaction of isothiocyanates with simple thioacids (three with thioacetic acid and one with indolethioacetic acid) and of none between isocyanates themselves and thioacids. The four examples of isothiocyanates and thioacids all make use of heating to 60 or 80 °C to achieve the reactions described, and none of the four papers makes reference to the original work of Kricheldorf and Leppert. (a) Gonda, J.; Martinkova, M.; Walko, M.; Zavacka, E.; Budesinsky, M.; Cisarova, I. Tetrahedron Lett. 2001, 42, 4401-4404.
  • 14
    • 0019529504 scopus 로고
    • For other amide bond forming reactions employing thioacids, see: a
    • For other amide bond forming reactions employing thioacids, see: (a) Blake, J. Int. Pept. Protein Res. 1981, 17, 273-274.
    • (1981) Int. Pept. Protein Res , vol.17 , pp. 273-274
    • Blake, J.1
  • 37
  • 42
    • 0003713167 scopus 로고    scopus 로고
    • Boons, G.-J, Ed, Blackie Academic and Professional: London
    • (b) Roy, R. In Carbohydrate Chemistry; Boons, G.-J., Ed.; Blackie Academic and Professional: London, 1998; pp 243-321.
    • (1998) Carbohydrate Chemistry , pp. 243-321
    • Roy, R.1
  • 45
    • 68149096402 scopus 로고    scopus 로고
    • In an attempt to accelerate the decomposition of the intermediate and improve the yield of 2 and 9, a number of Lewis acids, nBu2BOTf, BF3.OEt2, Sc(OTf) 3, Sn(OTf)2, Yb(OTf)3, TiCl4, CuBr2, Fe(acac)3, Cu(acac)2, Ti(O iPr)4, Zr(OiPr)4, and Sn(2-ethylhexanoate)2) were screened both with and without the addition of Hunig's base, unfortunately to no avail
    • 2) were screened both with and without the addition of Hunig's base, unfortunately to no avail.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.