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Volumn 40, Issue 13, 1999, Pages 2453-2456

Directed ortho metalation-cross coupling route to indolo-4,5- quinodimethanes. Synthesis of benz[e]indoles

Author keywords

[No Author keywords available]

Indexed keywords

INDOLE DERIVATIVE; INDOLO 4,5 QUINODIMETHANE; UNCLASSIFIED DRUG;

EID: 0033605818     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00247-6     Document Type: Article
Times cited : (14)

References (31)
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  • 2
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    • Department of Chemistry, Queen's University, Kingston, Ontario, K7L 3N6 CANADA; email: baderadm@chem.queensu.ca
    • (b) Department of Chemistry, Queen's University, Kingston, Ontario, K7L 3N6 CANADA; email: baderadm@chem.queensu.ca
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    • Mills, R. J.; Taylor, N. J.; Snieckus, V. J. Org. Chem. 1989, 54, 4372. For a study in the naphthalene series, see Puumala, K. M.Sc. Thesis, University of Waterloo, 1997.
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    • For example, reaction of 12 with methyl acrylate under CsF or TBAF conditions described for 13 gave, in addition to the expected cycloadducts 14, indole-N Michael addition products. Kinsman, A. C. M.Sc. Thesis, University of Waterloo, 1997.
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    • 13C COSY experiments on these mixtures suggested that the C-8 ester is the major isomer.
    • 13C COSY experiments on these mixtures suggested that the C-8 ester is the major isomer.
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    • X-ray structure of 17. (Formula presented)
    • X-ray structure of 17. (Formula presented)
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    • Control experiments indicated that this product distribution was the result of isomerization of dimethyl maleate under the reaction conditions coupled with the relatively rapid cycloaddition rate of dimethyl fumarate.
    • Control experiments indicated that this product distribution was the result of isomerization of dimethyl maleate under the reaction conditions coupled with the relatively rapid cycloaddition rate of dimethyl fumarate.
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    • 13C NMR, IR, LRMS and either elemental analysis or HRMS
    • 13C NMR, IR, LRMS and either elemental analysis or HRMS.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.