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Volumn 10, Issue 2, 2006, Pages 346-348

Practical synthesis of 2-amino-5-fluorothiazole hydrochloride

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EID: 33645550150     PISSN: 10836160     EISSN: None     Source Type: Journal    
DOI: 10.1021/op0502194     Document Type: Article
Times cited : (17)

References (31)
  • 6
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    • U.S. Patent 4,046,768
    • (a) Krenzer, J.; Wu, C. C. U.S. Patent 4,046,768; Chem. Abstr. 1977, 87, 184508.
    • (1977) Chem. Abstr. , vol.87 , pp. 184508
    • Krenzer, J.1    Wu, C.C.2
  • 7
    • 33645538753 scopus 로고
    • Br. Patent 1,579,771
    • (b) Wu, F.; Krenzer, J. Br. Patent 1,579,771; Chem. Abstr. 1978, 88,105336.
    • (1978) Chem. Abstr. , vol.88 , pp. 105336
    • Wu, F.1    Krenzer, J.2
  • 8
    • 33645536848 scopus 로고
    • U.S. Patent 4,086,240
    • (c) Wu, C. C.; Krenzer, J. U.S. Patent 4,086,240; Chem. Abstr. 1978, 89,109486.
    • (1978) Chem. Abstr. , vol.89 , pp. 109486
    • Wu, C.C.1    Krenzer, J.2
  • 9
    • 33645535528 scopus 로고
    • U.S. Patent 4,097,485
    • (d) Krenzer, J.; Wu, C. C. U.S. Patent 4,097,485; Chem. Abstr. 1978, 89, 197553.
    • (1978) Chem. Abstr. , vol.89 , pp. 197553
    • Krenzer, J.1    Wu, C.C.2
  • 13
    • 33645534759 scopus 로고    scopus 로고
    • PCT Int. Appl. WO 2005/014591, 17 February 2005
    • Mavro, J.; Vidal, L.; Saunier, J.-B. PCT Int. Appl. WO 2005/014591, 17 February 2005; Chem. Abstr. 2005, 142, 225134.
    • (2005) Chem. Abstr. , vol.142 , pp. 225134
    • Mavro, J.1    Vidal, L.2    Saunier, J.-B.3
  • 23
    • 0032763340 scopus 로고    scopus 로고
    • The fluorination of acetamidothiophenes with F-TEDA is also problematic, affording very low yields of the desired fluorinated products: Kobarfard, F.; Kauffman, J. M.; Boyko, W. J. J. Heterocycl. Chem. 1999, 36, 1247-1251.
    • (1999) J. Heterocycl. Chem. , vol.36 , pp. 1247-1251
    • Kobarfard, F.1    Kauffman, J.M.2    Boyko, W.J.3
  • 25
    • 33645550447 scopus 로고    scopus 로고
    • note
    • The only other electrophilic fluorinating agents commercially available in bulk at present are 1-fluoropyridinium pyridine heptafluorodiborate [AccuFluor NFPy] and 1-fluoro-4-hydroxy-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) [AccuFluor NFTh].
  • 28
    • 33645554388 scopus 로고    scopus 로고
    • note
    • It is believed that the proton source for the formation of 1c is NFSi itself, as quenching of the dianion with DMF gave a quantitative yield of the appropriate aldehyde.
  • 29
    • 33645539206 scopus 로고    scopus 로고
    • note
    • The difluorinated compound 2-tert-butoxycarbonylamino-4,5- difluorothiazole (5) was produced in 5-10% yield (determined by HPLC at 275 nm) when a larger quantity of t-BuLi (2.4 equiv) was employed.
  • 31
    • 33645544782 scopus 로고    scopus 로고
    • available via the Internet
    • This organometallic reagent was purchased on a multikilogram scale from Chemetall GmbH (Frankfurt a. M., Germany). CAUTION: t-BuLi is extremely pyrophoric and should be handled on a large scale only by experienced personnel. Solutions of t-BuLi react vigorously and often violently with oxygen, water, and other protic solvents. As a result, the reaction must be conducted with extreme care under a dry, oxygen free, inert atmosphere. Appropriate protective clothing should be worn, and a suitable safety shield should be employed. In case of fire, a dry-powder extinguisher should be used. For further information on the handling of t-BuLi solutions in large quantities, see: Bailey, W. F.; Longstaff, S. C. FMC Lithium Link, Fall 2000, tert-Butyllithium in Organic Synthesis (available via the Internet at http://www.fmclithium.com).
    • FMC Lithium Link, Fall 2000, Tert-Butyllithium in Organic Synthesis
    • Bailey, W.F.1    Longstaff, S.C.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.