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Volumn 50, Issue 6, 2009, Pages 684-687

Synthesis of new aza-bicyclic 2-isoxazolines by 1,3-dipolar cycloaddition of endocyclic enecarbamates and enamides with nitrile oxides

Author keywords

1,3 Dipolar cycloaddition; 2 Isoxazolines; Enamides; Endocyclic enecarbamates; Nitrile oxides

Indexed keywords

2 ISOXAZOLINE BISAMIDE; 4,5 DIHYDROISOXAZOLE[5,4 B]PIPERIDINE; 4,5 DIHYDROISOXAZOLE[5,4 B]PYRROLIDINE; AMIDE; AMINE; AZA BICYCLIC 2 ISOXAZOLINE; CARBAMIC ACID DERIVATIVE; ENAMIDE; ENDOCYCLIC ENECARBAMATE; ISOXAZOLINE DERIVATIVE; NITRILE OXIDE; PIPERIDINE DERIVATIVE; PYRROLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 57749195088     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.11.096     Document Type: Article
Times cited : (9)

References (24)
  • 7
    • 33947231700 scopus 로고    scopus 로고
    • Excellent reviews:
    • Excellent reviews:. Pellissier H. Tetrahedron 63 (2007) 3235
    • (2007) Tetrahedron , vol.63 , pp. 3235
    • Pellissier, H.1
  • 8
    • 57749195615 scopus 로고    scopus 로고
    • 1,3-Dipolar cycloaddition in 'Comprehensive Organic Synthesis' 1991, Vol. 5, pp 247-270.
    • 1,3-Dipolar cycloaddition in 'Comprehensive Organic Synthesis' 1991, Vol. 5, pp 247-270.
  • 15
    • 57749194680 scopus 로고    scopus 로고
    • note
    • 3N in dry THF, under reflux. The reaction mixture is left over reflux for additional 3 h. Next, THF is removed in vacuo and the crude enamide/enecarbamate purified by flash-chromatography: silica gel, ethyl acetate/hexane 1:10. Enamides and enecarbamates absorb iodine intensely on TLC.
  • 18
    • 2942584978 scopus 로고    scopus 로고
    • 4 and then concentrated in vacuo. The hydroximinoyl chlorides were used without further purification
    • 4 and then concentrated in vacuo. The hydroximinoyl chlorides were used without further purification
    • (2004) Tetrahedron Lett. , vol.45 , pp. 4931
    • Park, K.1    Marshall, W.J.2
  • 19
    • 57749207339 scopus 로고    scopus 로고
    • note
    • f for the cycloadduct on a TLC plate is smaller than that observed for the enamide/enecarbamate (UV, phosphomolybdic acid).
  • 23
    • 85099526929 scopus 로고    scopus 로고
    • note
    • 3, δ, 300 MHz, rt): 1.95 and 1.81 (m, 2H, rot), 2.13 (m, 2H); 3.81 and 3.57 (m, 2H, rot), 4.88 and 5.24 (m, 1H, rot), 6.45 and 7.23 (d, J = 8.1 Hz, 1H, rot), 7.10 (m, 2H), 7.51 (m, 2H).
  • 24
    • 57749208004 scopus 로고    scopus 로고
    • note
    • See the experimental procedures or spectra in the online version.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.