Scandium Triflate-Catalyzed Nucleophilic Additions to Indolylmethyl Meldrum’s Acid Derivatives via a Gramine-Type Fragmentation: Synthesis of Substituted Indolemethanes

Treatment of indolylmethyl Meldrum’s acids with catalytic scandium triflate and a variety of nucleophiles results in the nucleophilic displacement of the Meldrum’s acid moiety via a gramine-type fragmentation. The reaction is useful for the generation of heterocyclic compounds of significant molecul...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 78; no. 20; pp. 10534 - 10540
Main Authors Armstrong, Erin L, Grover, Huck K, Kerr, Michael A
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 18.10.2013
Amer Chemical Soc
Subjects
Catalysis
Chemistry
Chemistry, Organic
Dioxanes - chemistry
Heterocyclic Compounds - chemical synthesis
Heterocyclic Compounds - chemistry
Indoles - chemical synthesis
Indoles - chemistry
Mesylates - chemistry
Molecular Structure
Physical Sciences
Scandium - chemistry
Science & Technology
FUNCTIONALIZATION
3-ALKYLINDOLES
FRIEDEL-CRAFTS REACTION
BIS(INDOLYL)METHANES
QUATERNARY
INDOLES
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Summary:Treatment of indolylmethyl Meldrum’s acids with catalytic scandium triflate and a variety of nucleophiles results in the nucleophilic displacement of the Meldrum’s acid moiety via a gramine-type fragmentation. The reaction is useful for the generation of heterocyclic compounds of significant molecular complexity.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/jo4017524