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Volumn 52, Issue 13, 2011, Pages 1506-1508

Regioselectivity studies of sydnone cycloaddition reactions of azine-substituted alkynes

Author keywords

Cycloadditions; Pyrazoles; Regioselectivity; Sydnones

Indexed keywords

ALKYNE DERIVATIVE; SYDNONE DERIVATIVE;

EID: 79951946187     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.01.115     Document Type: Article
Times cited : (25)

References (23)
  • 3
    • 84876563501 scopus 로고    scopus 로고
    • Chem. Abstr. 2008, 149, 121249.
    • (2008) Chem. Abstr. , vol.149 , pp. 121249
  • 5
    • 79951958017 scopus 로고    scopus 로고
    • Chem. Abstr. 2009, 152, 57307.
    • (2009) Chem. Abstr. , vol.152 , pp. 57307
  • 7
    • 79951948385 scopus 로고    scopus 로고
    • Chem. Abstr. 2007, 146, 421980.
    • (2007) Chem. Abstr. , vol.146 , pp. 421980
  • 17
    • 27644475970 scopus 로고    scopus 로고
    • D.G. Hall, Wiley-VCH Weinheim
    • D.G. Hall, Boronic Acids 2005 Wiley-VCH Weinheim
    • (2005) Boronic Acids
  • 18
    • 79951955347 scopus 로고    scopus 로고
    • note
    • The reactions were run under microwave irradiation for convenience; however, reactions conducted in refluxing xylenes over 16 h gave similar yields and identical regioisomer ratios.
  • 19
    • 79951957822 scopus 로고    scopus 로고
    • note
    • Sydnones are known to be acid sensitive, and as 11 was completely consumed in this reaction, we attribute the low yield to the decomposition of this compound.
  • 20
    • 79951944207 scopus 로고    scopus 로고
    • note
    • Subjecting a 2:1 mixture of pyrazole regioisomers 14 to TsOH in refluxing ethylene glycol over 16 h did not result in a change of regioisomer ratios. This experiment confirms that the selectivity observed in the cycloaddition of ethynylpyridinium and 11 is not the result of selective decomposition of a 3-substituted pyrazole isomer.
  • 22
    • 79951943107 scopus 로고    scopus 로고
    • note
    • 8,13 and confirmed in the case of compound 24 by NOE spectroscopy. Regiosiomer ratios were estimated on crude reaction mixtures and confirmed by chromatographic separation in the case of compounds 12, 16, 17, 22 and 24.
  • 23
    • 79951959475 scopus 로고    scopus 로고
    • note
    • 3: 222.1031, found: 222.1031.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.