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Volumn 36, Issue 23, 1995, Pages 3993-3996

The behavior of indene oxide in the ritter reaction: A simple route to cis-aminoindanol

Author keywords

[No Author keywords available]

Indexed keywords

1 AMINO 2 INDANOL; INDAN DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0029070472     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)00696-A     Document Type: Article
Times cited : (130)

References (27)
  • 2
    • 84914005322 scopus 로고    scopus 로고
    • Poster presentations at the IX International Conference on AIDS; Berlin, Germany, June 6, 1993 and the 206th ACS National meeting, MEDI-6 Chicago, August 22, 1993.
  • 14
    • 0001893995 scopus 로고
    • EPOXIDATION OF OLEFINS BY HYDROGEN PEROXIDE-ACETONITRILE: cis-CYCLOOCTENE OXIDE
    • (1981) Organic Syntheses , vol.60 , pp. 63
    • Bach1    Knight2
  • 15
    • 84914005321 scopus 로고    scopus 로고
    • Other nitriles are comparable to acetonitrile in this reaction. However due to the expense (nitrile is used as the solvent) and the high toxicity of some of the nitriles, acetonitrile was deemed optimal.
  • 16
    • 84914005320 scopus 로고    scopus 로고
    • 3H without acetonitrile generated the indanone and mesylate 5b as the major compounds, along with several other by-products.
  • 17
    • 84914005319 scopus 로고    scopus 로고
    • Compounds 6, 8 and 9 were individually subjected to reflux in aqueous sulfuric acid. The corresponding aminoindanol was obtained with no detectable epimerization at the C-1 position. NMR study indicated that cis aminoindanol is obtained mainly via the acetate intermediate 14 by further hydrolysis as shown below.
  • 18
    • 84914005318 scopus 로고    scopus 로고
    • The 1-chloro- and 1-trifluroacetoxy-2-hydroxyindanes are stable products and do not ionize to the corresponding carbenium ion to provide compound 6. Increasing the temperature of the reaction media resulted in decomposition.
  • 19
    • 84914005317 scopus 로고    scopus 로고
    • 3 is critical in order to avoid ketone formation.
  • 20
    • 0002578608 scopus 로고
    • Asymmetric Catalytic Epoxidation of Unfunctionalized Olefins
    • For the preparation of chiral indene oxide via asymmetric metal catalysis, see, VCH, New York, Chapter 4.2
    • (1994) Catalytic Asymmetric Synthesis , pp. 159
    • Jacobsen1
  • 23
    • 0018078927 scopus 로고
    • Synthesis and absolute stereochemistry of cis- and trans-1,2-indandiols: metabolites of indene and 2-indanone
    • For the preparation of chiral indene oxide via microbiological transformation, see:
    • (1978) The Journal of Organic Chemistry , vol.43 , pp. 4540
    • Zeffer1    Imuta2
  • 25
    • 84914005316 scopus 로고    scopus 로고
    • 1S, 2R indene oxide was prepared in 〉99% ee from the racemic epoxide with epoxide hydrolase; Zhang, J.; Chartrain, M.; Grasham, R.; Senanayake, C.H. manuscript in preparation.
  • 27
    • 84914005315 scopus 로고    scopus 로고
    • Both cis- and transindandiol (15) with the correct stereochemistry at C-2 serve as sources of methyl oxazoline. Racemic 2-bromo-indan-1-ol (16) also provides racemic methyl oxazoline when the intermediate Ritter product, trans-1-acetamido-2-bromo indane, is heated.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.