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Volumn 69, Issue 4, 2004, Pages 1346-1352

Synthesis of Fused Tetrazole Derivatives via a Tandem Cycloaddition and N-Allylation Reaction and Parallel Synthesis of Fused Tetrazole Amines

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; BENZENE; BROMINE COMPOUNDS; DERIVATIVES; KETONES; SYNTHESIS (CHEMICAL);

EID: 1242307323     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo035498c     Document Type: Article
Times cited : (31)

References (39)
  • 14
    • 1242336249 scopus 로고    scopus 로고
    • Preparation of allylic aromatic compounds by reaction of aromatic amines with a nitrite and an allylic olefin; Eur. Patent 1013636; 2000; 11 pp.
    • Ek, F.; Wistrand, L. G. Preparation of allylic aromatic compounds by reaction of aromatic amines with a nitrite and an allylic olefin; Eur. Patent 1013636; 2000; 11 pp.
    • Ek, F.1    Wistrand, L.G.2
  • 19
    • 1242291289 scopus 로고    scopus 로고
    • Imidazodiazepine derivatives and intermediates for their preparation, medicaments containing them and their therapeutic application; Eur. Patent 27214; 1981; 116 pp
    • Haefely, W.; Hunkeler, W.; Kyburz, E.; Moehler, H.; Pieri, L.; Polc, P.; Gerecke, M. Imidazodiazepine derivatives and intermediates for their preparation, medicaments containing them and their therapeutic application; Eur. Patent 27214; 1981; 116 pp.
    • Haefely, W.1    Hunkeler, W.2    Kyburz, E.3    Moehler, H.4    Pieri, L.5    Polc, P.6    Gerecke, M.7
  • 25
    • 1242268706 scopus 로고    scopus 로고
    • Process for preparation of 5-substituted tetrazoles; Eur. Patent 796852; 1997; 22 pp.
    • Koguro, K.; Oga, T.; Tokunaga, N.; Mitsui, S.; Orita, R. Process for preparation of 5-substituted tetrazoles; Eur. Patent 796852; 1997; 22 pp.
    • Koguro, K.1    Oga, T.2    Tokunaga, N.3    Mitsui, S.4    Orita, R.5
  • 28
    • 1242268711 scopus 로고    scopus 로고
    • note
    • Conformational analysis using PcSpartan Pro (AM1).
  • 29
    • 0033518276 scopus 로고    scopus 로고
    • The overlay was done in Chem3D using a reported low-energy conformation of 24, See: Tønder et al. J. Med. Chem. 1999, 42, 4970-4980.
    • (1999) J. Med. Chem. , vol.42 , pp. 4970-4980
    • Tønder1
  • 36
    • 1242336251 scopus 로고    scopus 로고
    • note
    • 2 and 1,2-dichloroethane reacted with the amines in the reaction mixture, which resulted in other amines than the product.
  • 37
    • 1242268710 scopus 로고    scopus 로고
    • note
    • f value from the other substances. To obtain a pure product, it was therefore important to consume all starting material.
  • 38
    • 1242291291 scopus 로고    scopus 로고
    • note
    • The allylation reactions gave approximately 2.0 mmol of nitrile-containing products and byproducts. Therefore, the amounts of DBTO and (TMS)N3 used in the tandem reaction were based on the fact that the reaction mixture contained 2 mmol of crude allylic bromide. However, the final yields of the fused tetrazoles were calculated using the yields (internal standard) from the allylation reactions.
  • 39
    • 1242313736 scopus 로고    scopus 로고
    • note
    • 2, which complicated these reactions. However, additional solvent and a change in the solvent composition remedied this problem. Also, the corresponding products 11c and 11f had poor solubility in common solvents, but recrystallization without prior chromatography gave the pure compounds.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.