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Volumn 48, Issue 44, 2009, Pages 8325-8327

Synthesis of pyridines and pyrazines using an intramolecular hydroamination-based reaction sequence

Author keywords

Alkynes; Homogeneous catalysis; Hydroaminatlon; Nitrogen heterocycles; Sustainable chemistry

Indexed keywords

ALKYNES; HOMOGENEOUS CATALYSIS; HYDROAMINATLON; NITROGEN HETEROCYCLES; SUSTAINABLE CHEMISTRY;

EID: 70350010210     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200903922     Document Type: Article
Times cited : (54)

References (62)
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  • 21
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    • Eds.: M. Beller, C. Bolm, Wiley-VCH, Weinheim
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  • 30
    • 0003748618 scopus 로고    scopus 로고
    • Eds.: S. Murahashi, S. G. Davies, Blackwell Science, Oxford
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  • 38
    • 34247624623 scopus 로고    scopus 로고
    • Angew. Chem Int. Ed. 2007, 46, 2074. For examples of related cyclizations of alkynyl imines, see:
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  • 46
    • 70350039937 scopus 로고    scopus 로고
    • See references [6g] and [6i] for specific examples of pyridine ring formation from 2-en-4-yn-1-imines.
    • See references [6g] and [6i] for specific examples of pyridine ring formation from 2-en-4-yn-1-imines.
  • 54
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    • Such reactions are also called reverse Cope cyclizations/eliminations. For a review: N. J. Cooper, D W Knight, Tetrahedron 2004, 60, 243.
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    • Cooper, N.J.1    Knight, D.W.2
  • 61
    • 70350027514 scopus 로고    scopus 로고
    • After cyclization, intermediate II could be formed after deprotonation (III→IV) and isomerization (IV→II). So far, all attempts to observe reaction intermediates by NMR methods have not been fruitful.
    • After cyclization, intermediate II could be formed after deprotonation (III→IV) and isomerization (IV→II). So far, all attempts to observe reaction intermediates by NMR methods have not been fruitful.
  • 62
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    • note
    • The use of the milder reaction conditions A is generally optimal for aldoximes (which tend to decompose at higher temperatures) or for cyclization onto terminal alkynes (which are typically more facile). To provide calibration on the usual reaction conditions, substrate la provided the desired pyridine 2a in 73 % yield after 2 h as determined by NMR methods, whereas only a 14% yield was observed after 6 h at 100 °C (NMR methods). By NMR methods, most of the mass balance proved to be unreacted starting material.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.