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European Journal of Organic Chemistry
Volumn , Issue 13, 2009, Pages 2185-2189
Synthesis of indoles by intermolecular cyclization of unfunctionalized nitroarenes and alkynes: one-step synthesis of the skeleton of fluvastatin
Author keywords

Alkynes ; Arenes ; Carbonylation; Nitrogen heterocycles ; Palladium
Indexed keywords

EID: 66149105405     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200801274     Document Type: Article
Times cited : (49)
References (41)
  • 3
    • 33747092660 scopus 로고    scopus 로고
    • For reviews on the applications of reduction reactions of ni- troarenes by CO in fine chemistry, see: a
    • For reviews on the applications of reduction reactions of ni- troarenes by CO in fine chemistry, see: a) F. Ragaini, S. Cenini, E. Gallo, A. Caselli, S. Fantauzzi, Curr. Org. Chem. 2006, 10, 1479-1510
    • (2006) Curr. Org. Chem , vol.10 , pp. 1479-1510
    • Ragaini, F.1    Cenini, S.2    Gallo, E.3    Caselli, A.4    Fantauzzi, S.5
  • 5
    • 66149104588 scopus 로고    scopus 로고
    • For the literature before 1996, see ch. 5 in ref.[8].
    • c) For the literature before 1996, see ch. 5 in ref.[8].
  • 21
    • 66149137345 scopus 로고    scopus 로고
    • The use ofDMF as solvent has been reported to be instrumental for allowing indole synthesis by cyclization of o-nitrosty- renes by palladium-phenanthroline catalysts under mild conditions 100 °C and ca. 2 bar CO pressure, 19] We tested these mild conditions in the present system, but only a 6.3% conversion was observed
    • The use ofDMF as solvent has been reported to be instrumental for allowing indole synthesis by cyclization of o-nitrosty- renes by palladium-phenanthroline catalysts under mild conditions (100 °C and ca. 2 bar CO pressure).[19] We tested these mild conditions in the present system, but only a 6.3% conversion was observed.
  • 25
    • 66149087416 scopus 로고    scopus 로고
    • The 13C NMR and 19F NMR spectra for 3c have never been described in the literature and are here reported for the first time.
    • The 13C NMR and 19F NMR spectra for 3c have never been described in the literature and are here reported for the first time.
  • 29
    • 66149144446 scopus 로고    scopus 로고
    • J. K. Perregaard, K. Andersen, Eur. Pat. EP 470039 A2 19920205, 1992.
    • J. K. Perregaard, K. Andersen, Eur. Pat. EP 470039 A2 19920205, 1992.
  • 30
    • 66149090071 scopus 로고    scopus 로고
    • The formation of 3c can be skipped in the preparation of Flu- vastatin if the isopropyl group is introduced before the cycliza- tion reaction described in ref.[24,28] However, this is not possible in other cases. Starting from 3c, Fluvastatin can be obtained by N-alkylation with an isopropyl group by well-established procedures,[29-31] followed by introduction of the chiral substit- uent as reported in the literature.[28,32]
    • The formation of 3c can be skipped in the preparation of Flu- vastatin if the isopropyl group is introduced before the cycliza- tion reaction described in ref.[24,28] However, this is not possible in other cases. Starting from 3c, Fluvastatin can be obtained by N-alkylation with an isopropyl group by well-established procedures,[29-31] followed by introduction of the chiral substit- uent as reported in the literature.[28,32]
  • 36
    • 66149154759 scopus 로고    scopus 로고
    • Alkynes are also central to some alternative synthetic strategies for the synthesis of indoles. These have been very recently reviewed by Beller and coworkers.[34] Indoles bearing an aryl group in the 3-position have been obtained in only a few cases by these reactions and the 2-position was also substituted in all cases.[35-38] So these approaches cannot yield 3c.
    • Alkynes are also central to some alternative synthetic strategies for the synthesis of indoles. These have been very recently reviewed by Beller and coworkers.[34] Indoles bearing an aryl group in the 3-position have been obtained in only a few cases by these reactions and the 2-position was also substituted in all cases.[35-38] So these approaches cannot yield 3c.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.