A Convenient Synthesis of 8-Substituted Indolizines as Precursors to 5-Substituted Cycl{3.2.2}azine Derivatives

Journal of Heterocyclic Chemistry

Volumn 34, Issue 5, 1997, Pages 1441-1446

  Smith, Jonathan O ^a   Mandal, Braja K ^a  

^a Illinois Institute of Technology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000845343     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570340511     Document Type: Article

References (24)

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12. [9a] To exemplify the stability of 4b in the reaction mixture, its' treatment with p-toluenesulfonic acid (0.50 equivalent) over a 24 hours period in refluxing toluene, resulted in 98% isolated yield of 5b, and quantitative recovery of unreacted 4b based on p-toluenesulfonic acid added. Likewise, treatment of 4a gave 5a (70%), and near quantitative recovery of unreacted 4a. Corey and co-workers [18] have reported the use of similar compounds, such as 5a,b as silylating agents for tertiary or hindered secondary alcohols. Specifically, triisopropylsilyl triflate and tert-butyldimethylsilyl triflate. Indeed, the reaction of 5b, benzyl alcohol, 2,6-lutidine in dichloromethane at molar ratios of {1.1:1:2} resulted in silylation of the alcohol at room temperature. Also, the reaction of 5a, tert-butyl alcohol, and 2,6-lutidine in dichloromethane at molar ratios of {1.3:1:2.2} resulted in silylation of the alcohol at room temperature [3];
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