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Volumn 50, Issue 20, 2009, Pages 2293-2297

An efficient access to 3,6-disubstituted 1H-pyrazolo[3,4-b]pyridines via a one-pot double SNAr reaction and pyrazole formation

Author keywords

2,6 difluoro 3 ketopyridines; Double SNAr reaction; Lithiation; One pot synthesis; Pyrazole formation

Indexed keywords

2 TERT BUTYLAMINO 2 FLUORO 3 BENZOTHIOPHENOYLPYRIDINE; 2,6 DIFLUORO 3 KETOPYRIDINE DERIVATIVE; 6 TERT BUTYLAMINO 2 FLUORO 3 BENZOTHIOPHENOYLPYRIDINE; HYDRAZINE; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 63349096176     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.02.142     Document Type: Article
Times cited : (21)

References (32)
  • 9
    • 63349092928 scopus 로고    scopus 로고
    • Ref. 2
    • Ref. 2.
  • 22
    • 63349107593 scopus 로고    scopus 로고
    • Ref. 3
    • Ref. 3.
  • 26
    • 63349096831 scopus 로고    scopus 로고
    • note
    • + 324.0062, found 324.0046.
  • 27
    • 0034533365 scopus 로고    scopus 로고
    • Methylamine substitution of 2,6-difluoropyridine-3-carboxylic esters gave a mixture of methyl 2-fluoro-6-methylaminopyridine-3-carboxylate and methyl-6-fluoro-2-methylaminopyridine-3-carboxylate in a ratio of 1.8:1-1:3 depending on the solvent used. Please see:
    • Methylamine substitution of 2,6-difluoropyridine-3-carboxylic esters gave a mixture of methyl 2-fluoro-6-methylaminopyridine-3-carboxylate and methyl-6-fluoro-2-methylaminopyridine-3-carboxylate in a ratio of 1.8:1-1:3 depending on the solvent used. Please see:. Hirokawa Y., Horikawa T., and Kato S. Chem. Pharm. Bull. 48 (2000) 1847
    • (2000) Chem. Pharm. Bull. , vol.48 , pp. 1847
    • Hirokawa, Y.1    Horikawa, T.2    Kato, S.3
  • 30
    • 63349096047 scopus 로고    scopus 로고
    • note
    • 35 wt% of hydrazine aqueous also worked well.
  • 31
    • 34250202185 scopus 로고    scopus 로고
    • The 6-N-tert-butyl group of 6-tert-butylamino-3-substituted-1H-pyrazolo[3,4-b]pyridines 5a-k could be easily removed to generate the corresponding 6-amino-3-substituted-1H-pyrazolo[3,4-b]pyridines by TFA treatment. Please see:
    • The 6-N-tert-butyl group of 6-tert-butylamino-3-substituted-1H-pyrazolo[3,4-b]pyridines 5a-k could be easily removed to generate the corresponding 6-amino-3-substituted-1H-pyrazolo[3,4-b]pyridines by TFA treatment. Please see:. Yin J., Xiang B., Huffman M.A., Raab C.E., and Davies I.W. J. Org. Chem. 72 (2007) 4554
    • (2007) J. Org. Chem. , vol.72 , pp. 4554
    • Yin, J.1    Xiang, B.2    Huffman, M.A.3    Raab, C.E.4    Davies, I.W.5
  • 32
    • 63349103729 scopus 로고    scopus 로고
    • note
    • 3) δ 157.9, 152.8, 137.9, 137.7, 135.8, 135.4, 131.5, 128.7, 126.7, 122.2, 121.8, 117.5, 108.1, 105.7, 51.7, 29.2, 21.6.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.