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Volumn 128, Issue 17, 2006, Pages 5646-5647

Synthesis of the pyrazolo[4,3-e][1,2,4]triazine family of natural products: Nostocine A, fluviol A, and pseudoiodinine

Author keywords

[No Author keywords available]

Indexed keywords

1,2,4 TRIAZINE DERIVATIVE; FLUVIOL A; NATURAL PRODUCT; NOSTOCINE A; PSEUDOIODININE; PYRAZOLE DERIVATIVE; PYRAZOLO[4,3 E][1,2,4]TRIAZINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 33646537465     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja060937l     Document Type: Article
Times cited : (35)

References (24)
  • 1
    • 33646564160 scopus 로고    scopus 로고
    • note
    • 20 have both been stated by others not to occur naturally.
  • 7
    • 33646544147 scopus 로고    scopus 로고
    • note
    • Procedure adapted from the synthesis of 5-hydrazinocarbonyl-4,5-dihydro- 1,2,4-triazin-6(1H)-one reported in ref 6.
  • 12
    • 0010578203 scopus 로고
    • Sutherland, I. O., Ed.; Pergamon: Oxford
    • (b) Atkinson, R. S. In Comprehensive Organic Chemistry, Sutherland, I. O., Ed.; Pergamon: Oxford. 1979; Vol. 2. p 219.
    • (1979) Comprehensive Organic Chemistry , vol.2 , pp. 219
    • Atkinson, R.S.1
  • 13
    • 37049095365 scopus 로고
    • The structure of normethylpseudoiodinine was determined by X-ray crystallography, which is regarded as an absolute method, but the literature is replete with erroneous X-ray structures: See. for example: (a) Jones, P. G. Chem. Soc. Rev. 1984, 13, 157-172.
    • (1984) Chem. Soc. Rev. , vol.13 , pp. 157-172
    • Jones, P.G.1
  • 17
    • 33646591329 scopus 로고    scopus 로고
    • note
    • Hydrazine itself is symmetrical. In contrast to the situation with methylhydrazine, the reason for the Boc protection in the present case is to suppress reaction of hydrazine with two molecules of 8, which was a significant side reaction.
  • 18
    • 33646549052 scopus 로고    scopus 로고
    • note
    • Less than 1 equiv per cycle was used to suppress dimethylation.
  • 19
    • 33646584284 scopus 로고    scopus 로고
    • note
    • See Supporting Information.
  • 20
    • 0011991438 scopus 로고
    • 5 3-hydroxypyrazoles exist primarily as the hydroxy rather than oxo tautomer in nonpolar media: Katritzky, A. R.; Maine, F. W. Tetrahedron 1964, 20, 315-322.
    • (1964) Tetrahedron , vol.20 , pp. 315-322
    • Katritzky, A.R.1    Maine, F.W.2
  • 21
    • 0003873024 scopus 로고    scopus 로고
    • Chemical Databases Online, welcome-main Web version 2004, Chapman & Hall/CRC Press
    • Dictionary of Natural Products, Chemical Databases Online, http://www.chemnetbase.com/scripts/dnpweb.exe?welcome-main Web version 2004, Chapman & Hall/CRC Press.
    • Dictionary of Natural Products
  • 24
    • 0001678426 scopus 로고    scopus 로고
    • Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Ramsden, C. A., Eds.; Pergamon: Oxford
    • Knowles, P. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Ramsden, C. A., Eds.; Pergamon: Oxford, 1996; Vol. 7, p 511.
    • (1996) Comprehensive Heterocyclic Chemistry II , vol.7 , pp. 511
    • Knowles, P.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.