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Volumn 31, Issue 16, 1990, Pages 2333-2336

Annulation of imidazolines: A 1,3-dipolar cycloaddition route to pyrroloimidazoles, pyrrolidines and pyrroles

Author keywords

[No Author keywords available]

Indexed keywords

2 IMIDAZOLINE DERIVATIVE; PYRIDINE DERIVATIVE; PYRROLE DERIVATIVE;

EID: 0025218813     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(90)80221-7     Document Type: Article
Times cited : (35)

References (21)
  • 5
    • 85065119512 scopus 로고
    • Azomethine Ylids, Azomethine Imines, and Iminophosphoranes in Organic Syntheses
    • (1973) Synthesis , pp. 469
    • Stuckwisch1
  • 13
    • 84918636356 scopus 로고    scopus 로고
    • Prepared from N-benzyl-1,2-dinminoethane and triethyl orthoformate (4 mol. equiv.; p-TsOH, 0.05 mol equiv.; 72%).
  • 14
    • 84918627303 scopus 로고    scopus 로고
    • All new compounds gave spectral data (i.r., u.v., n.m.r., m.s.) in accord with the assigned structure, and satisfactory combustion analysis or accurate mass measurement.
  • 18
    • 84918621251 scopus 로고    scopus 로고
    • This reaction stereochemistry can be rationalised by assuming the anti conformation (i) of the dipole and an endo transition state (cf. ref. 1c). The failure to observe n.O.e, enhancements involving C-5(H) leaves open the possibility of the opposite configuration at C-5.
  • 20
    • 84918599259 scopus 로고    scopus 로고
    • Removal of the pendant chain at N-1 should be possible via chemistry we have developed in the tetrahydropyridine series (ref. 3a), to access 2,4-disubstituted pyrroles.
  • 21
    • 84918634567 scopus 로고    scopus 로고
    • Related eliminations from the products of azomethine ylide cycloaddition have been reported, e.g. refs. 1a,d.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.