Synthetic applications of azolium ylides to a traceless solid-phase synthesis of 2-substituted azoles

Organic Letters

Volumn 4, Issue 23, 2002, Pages 4017-4020

  Deng, Yijun ^a   Hlasta, Dennis J ^a  

^a JOHNSON AND JOHNSON PHARMACEUTICAL RESEARCH AND DEVELOPMENT   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; PYRROLE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; SYNTHESIS;

AZOLES; INDICATORS AND REAGENTS; MODELS, MOLECULAR; MOLECULAR CONFORMATION;

EID: 0037078805     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0266727     Document Type: Article

References (29)

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16. General Procedure. To carboxypolystyrene resin (1 g, 1.10 mmol/g, from Novabiochem) in dichloroethane (20 mL) was added 2-chloro-1,3-dimethylimidazolinium chloride (3 equiv) and N,N-diisopropylethylamine (6 equiv). The resulting mixture was shaken at room temperature for 4 h, followed by addition of 1-benzylimidazole (3 equiv) and benzaldehyde (5 equiv) and shaken for another 24 h at room temperature. The solvent was drained, and the resin was washed three times with dichloromethane and dried under vacuum.
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21. 2O (1.5 equiv) gave the best results.
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28. The yield is based on the loading of 2 (70% determined by elemental analysis).
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